- One-pot Synthesis of 4-Aminocyclohexanol Isomers by Combining a Keto Reductase and an Amine Transaminase
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The efficient multifunctionalization by one-pot or cascade catalytic systems has developed as an important research field, but is often challenging due to incompatibilities or cross-reactivities of the catalysts leading to side product formation. Herein we report the stereoselective preparation of cis- and trans-4-aminocyclohexanol from the potentially bio-based precursor 1,4-cyclohexanedione. We identified regio- and stereoselective enzymes catalyzing reduction and transamination of the diketone, which can be performed in a one-pot sequential or cascade mode. For this, we identified regioselective keto reductases for the selective mono reduction of the diketone to give 4-hydroxycyclohexanone. The system is modular and by choosing stereocomplementary amine transaminases, both cis- and trans-4-aminocyclohexanol were synthesized with good to excellent diastereomeric ratios. Furthermore, we identified an amine transaminase that produces cis-1,4-cyclohexanediamine with diastereomeric ratios >98 : 2. These examples highlight that the high selectivity of enzymes enable short and stereoselective cascade multifunctionalizations to generate high-value building blocks from renewable starting materials. Introduction.
- Sviatenko, Olha,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Venkata Manideep, Kollipara,Merdivan, Simon,Günther, Sebastian,Süss, Philipp,H?hne, Matthias
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- Histone Deacetylase Inhibitor (HDACi) Conjugated Polycaprolactone for Combination Cancer Therapy
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The short chain fatty acid, 4-phenylbutyric acid (PBA), is used for the treatment of urea cycle disorders and sickle cell disease as an endoplasmic reticulum stress inhibitor. PBA is also known as a histone deacetylase inhibitor (HDACi). We report here the effect of combination therapy on HeLa cancer cells using PBA as the HDACi together with the anticancer drug, doxorubicin (DOX). We synthesized γ-4-phenylbutyrate-?-caprolactone monomer which was polymerized to form poly(γ-4-phenylbutyrate-?-caprolactone) (PPBCL) homopolymer using NdCl3·3TEP/TIBA (TEP = triethyl phosphate, TIBA = triisobutylaluminum) catalytic system. DOX-loaded nanoparticles were prepared from the PPBCL homopolymer using poly(ethylene glycol) as a surfactant. An encapsulation efficiency as high as 88% was obtained for these nanoparticles. The DOX-loaded nanoparticles showed a cumulative release of >95% of DOX at pH 5 and 37 °C within 12 h, and PBA release was monitored by 1H NMR spectroscopy. The efficiency of the combination therapy can notably be seen in the cytotoxicity study carried out on HeLa cells, where only ～20% of cell viability was observed after treatment with the DOX-loaded nanoparticles. This drastic cytotoxic effect on HeLa cells is the result of the dual action of DOX and PBA on the DNA strands and the HDAC enzymes, respectively. Overall, this study shows the potential of combination treatment with HDACi and DOX anticancer drug as compared to the treatment with an anticancer drug alone.
- Kularatne, Ruvanthi N.,Washington, Katherine E.,Bulumulla, Chandima,Calubaquib, Erika L.,Biewer, Michael C.,Oupicky, David,Stefan, Mihaela C.
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- Ionic liquids based on the 7-azabicyclo[2.2.1]heptane skeleton: Synthesis and properties
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Based on a previously developed method for the synthesis of epibatidine analogues, a series of new ionic liquids, based on the 7-azabicyclo[2.2.1] heptane skeleton, have been synthesized. The chemical and physical properties of the ionic liquids with bis(trifluoromethylsulfonyl)imide (Tf2N) and dicyanamide [N(CN)2] anions were investigated and they were found to exhibit very good electrochemical and thermal stabilities. Ionic liquids with the cationic part based on the structure of epibatidine (a 7-azabicyclo[2.2.1] skeleton) have been prepared. The chemical and physical properties of these ionic liquids with dicyanamide and bis(trifluoromethylsulfonyl)imide anions were investigated and they were found to show very good electrochemical and thermal stability. Copyright
- De Vos, Nils,Maton, Cedric,De Vreese, Peter,Brooks, Neil R.,Binnemans, Koen,Stevens, Christian V.
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- High-Cluster (Cu9) Cage Silsesquioxanes: Synthesis, Structure, and Catalytic Activity
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Unusual high-cluster (Cu9) cage phenylsilsesquioxanes were obtained via complexation of in situ CuII,Na-silsesquioxane species formed with phenanthroline and neocuproine. In the first case, phenanthroline, acting as "a silent ligand" (not participating in the composition of the final product), favors the formation of an unprecedented cagelike phenylsilsesquioxane of Cu9Na6 nuclearity, 1. In the second case, neocuproine ligands withdraws two Cu ions from the metallasilsesquioxane matrix, producing two cationic fragments Cu+(neocuproine)2. The remaining metallasilsesquioxane is rearranged into an anionic cage of Cu9Na4 nuclearity, finalizing the formation of a specific ionic complex, 2. The impressive molecular architecture of both types of complexes, e.g., the presence of different (cyclic/acyclic) types of silsesquioxane ligands, was established by single-crystal X-ray diffraction studies. Compound 1 was revealed to be highly active in the oxidative amidation of benzylic alcohol and the catalyst loading could be reduced down to 100 ppm of Cu. Catalytic studies of compound 1 demonstrated its high activity in hydroperoxidation of alkanes with H2O2 and oxidation of alcohols to ketones with tert-BuOOH.
- Astakhov, Grigorii S.,Bilyachenko, Alexey N.,Korlyukov, Alexander A.,Levitsky, Mikhail M.,Shul'Pina, Lidia S.,Bantreil, Xavier,Lamaty, Frédéric,Vologzhanina, Anna V.,Shubina, Elena S.,Dorovatovskii, Pavel V.,Nesterov, Dmytro S.,Pombeiro, Armando J. L.,Shul'Pin, Georgiy B.
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- Stereoselective conjugate addition directed by an enantiomerically pure ketal. Preparation of the cyclohexanone fragment of N-methylwelwitindolinone C isothiocyanate
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A cyclohexanone intermediate to be employed in the synthesis of the marine natural product N-methylwelwitindolinone C isothiocyanate has been prepared. The synthesis is diastereoselective for the production of the C12 quaternary center, which is obtained via a conjugate addition reaction directed by an adjacent chiral, nonracemic ketal. A single crystal X-ray analysis of a derivative of the final product established the absolute stereochemistry at C12.
- Konopelski, Joseph P.,Deng, Hongbo,Schiemann, Kai,Keane, Joseph M.,Olmstead, Marilyn M.
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- The mechanism of the tertiary amine catalysed isomerisation of endoperoxides to hydroxyketones: Synthesis and chemistry of the intermediate postulated in the peroxide attack mechanism
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Evidence is presented which demonstrates that the Kornblum-DeLaMare rearrangement does not proceed via nucleophilic attack of the peroxide linkage.
- Kelly, David R.,Bansal, Harjinder,Morgan
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- NMR spectroscopic conformational analysis of 4‐methylene‐ cyclohexyl pivalate—the effect of sp2 hybridization
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The conformational equilibrium of the axial/equatorial conformers of 4‐methylene ‐cyclohexyl pivalate is studied by dynamic NMR spectroscopy in a methylene chloride/freon mixture. At 153 K, the ring interconversion gets slow on the nuclear magnetic resonance timescale, the conformational equilibrium (?ΔG°) can be examined, and the barrier to ring interconversion (ΔG#) can be determined. The structural influence of sp2 hybridization on both ΔG° and ΔG#of the cyclohexyl moiety can be quantified.
- Kleinpeter, Erich,Heydenreich, Matthias,Koch, Andreas,Krtitschka, Angela,Krüger, Tobias,Linker, Torsten
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- Liquid-Phase Catalytic Hydrogenation of 1,4-Cyclohexanedione: Activity and Selectivity
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Liquid-phase catalytic hydrogenation of 1,4-cyclohexanedione was carried out by using various metal catalysts on SiO2 (Ni, Cu, Pd, Pt ,Ir, Ru) in 2-propanol as solvent under low hydrogen pressure, 6.2 bar, and 20 deg C.A kinetically consecutive process, diketone -> ketol -> diol, is obtained , and 4-hydroxycyclohexanone may be obtained in a single step at a yield of 70percent by utilizing Ru/SiO2.The rate and the selectivity for the first step of the reaction giving the ketol were examined as a function of several parameters: hydrogen pressure, substrate concentration, and temperature.The kinetic orders are 1 in H2 and -0.6 in diketone with an activation energy of 11 kcal/mol.
- Bonnet, Marc,Geneste, Patrick,Rodrigues, Marcel
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- Microreactors for oxidations using fluorine
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Continuous flow gas-liquid thin film microreactors have been effectively used for the oxidation of alcohols and Baeyer-Villiger oxidation of ketones using elemental fluorine.
- Chambers, Richard D.,Holling, Darren,Rees, Anthony J.,Sandford, Graham
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- POLITAG-Pd(0) catalyzed continuous flow hydrogenation of lignin-derived phenolic compounds using sodium formate as a safe H-source
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Phenols are aromatic biobased compounds and as they are accessible from lignin depolymerization, they can be a useful platform chemicals to produce value-added products. Herein we report our recent investigations on the definition of an approach to the efficient continuous flow selective hydrogenation of phenols in water. Our protocol is based on the use of sodium formate as a clean and safe hydrogen source in combination with our newly defined heterogeneous POLITAG-Pd(0) catalytic system. POLITAG is a polymeric heterogeneous support decorated with pincer-type ionic ligands proven to be highly efficient for the stabilization of Pd(0) nanoparticles. The results obtained are remarkable in comparison with other protocols that employ sodium formate as H-source. Indeed, our investigation has been extended to a variety of differently substituted phenolic compounds that have been hydrogenated with excellent to good selectivity in continuous flow conditions. Durability of the catalyst has been also tested with a representative continuous processing of over 100 mmol that showed no loss in efficiency and minimal metal leaching.
- Campana, Filippo,Ferlin, Francesco,Silvetti, Matteo,Trombettoni, Valeria,Vaccaro, Luigi,Valentini, Federica
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- Trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives
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A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a commercially available heterogeneous palladium catalyst is reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite cis-isomers. The diastereoselectivity of the phenol hydrogenation can be switched to the cis-isomers by employing rhodium-based catalysts. Moreover, a protocol for the chemoselective hydrogenation of phenols to cyclohexanones was developed.
- Bergander, Klaus,Glorius, Frank,Heusler, Arne,Wollenburg, Marco
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p. 11365 - 11370
(2020/11/24)
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- AMINOPYRIMIDINE COMPOUND
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The present invention provides a compound having a CaMKII inhibitory action, which is expected to be useful as an agent for the prophylaxis or treatment of cardiac diseases (particularly catecholaminergic polymorphic ventricular tachycardia, postoperative atrial fibrillation, heart failure, fatal arrhythmia) and the like. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.
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Paragraph 1085; 1531-1532
(2020/04/10)
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- Hydrogenation of Phenol to Cyclohexanone over Bifunctional Pd/C-Heteropoly Acid Catalyst in the Liquid Phase
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Abstract: Cyclohexanone is an important intermediate in the manufacture of polyamides in chemical industry, but direct selective hydrogenation of phenol to cyclohexanone under mild conditions is a challenge. Hydrogenation of phenol to cyclohexanone has been investigated in the presence of the composite catalytic system of Pd/C-heteropoly acid. 100% conversion of phenol and 93.6% selectivity of cyclohexanone were achieved within 3?h under 80?°C and 1.0?MPa hydrogen pressure. It has been found that a synergetic effect of Pd/C and heteropoly acid enhanced the catalytic performance of the composite catalytic system which suppressed the hydrogenation of cyclohexanone to cyclohexanol. Graphic Abstract: [Figure not available: see fulltext.].
- Liu, Shiwei,Han, Jing,Wu, Qiong,Bian, Bing,Li, Lu,Yu, Shitao,Song, Jie,Zhang, Cong,Ragauskas, Arthur J.
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p. 2383 - 2389
(2019/06/19)
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- Amorphous Cr/SiO2 Materials Hydrothermally Treated: Liquid Phase Cyclohexanol Oxidation
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Abstract: Amorphous Cr–SiO2 materials were synthesized by the sol–gel method and hydrothermally treated at temperatures between 150 and 220?°C. These materials were used as catalysts for cyclohexanol oxidation with H2O2 as oxidant and CH3CN as a solvent. They were responsible for the decomposition of H2O2, which triggers, by a free?radical mechanism in the homogeneous phase, the oxidation or degradation of the hydrocarbon chain. Metal leaching causes a drop in catalytic activity when the material is recycled. Studies on the hydrothermal treatment effect on the leaching process have demonstrated that the higher the hydrothermal treatment temperature, the higher the metal/support interaction, leading to a diminution of the leaching process. Under mild reaction conditions, and using TBHP as oxidant, leaching was reduced, and improvements were obtained on the selectivity towards the formation of cyclohexanone. The use of these catalysts in the oxidation of verbenol, an allylic alcohol, showed a significant increase in the substrate conversion and in the selectivity to carbonyl derivative formation. Graphical Abstract: [Figure not available: see fulltext.].
- Miranda, José Feliciano,Cuesta Zapata, Pablo M.,Gonzo, Elio E.,Parentis, Mónica L.,Davies, Lilian E.,Bonini, Norberto A.
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p. 2082 - 2094
(2018/05/28)
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- Synthesis and NMR spectroscopic conformational analysis of benzoic acid esters of mono- and 1,4-dihydroxycyclohexane, 4-hydroxycyclohexanone and the -ene analogue – The more polar the molecule the more stable the axial conformer
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para-Substituted benzoic acid esters of cyclohexanol, 1,4-dihydroxycyclohexane, 4-hydroxy-cyclohexanone and of the corresponding exo-methylene derivative were synthesized and the conformational equilibria of the cyclohexane skeleton studied by low temperature 1H and 13C NMR spectroscopy. The geometry optimized structures of the axial/equatorial chair conformers were computed at the DFT level of theory. Only one preferred conformation of the ester group was obtained for both the axial and the equatorial conformer, respectively. The content of the axial conformer increases with growing polarity of the 6-membered ring moiety; hereby, in addition, the effect of sp2 hybridization/polarity of C(4)=O/C(4)=CH2 on the present conformational equilibria is critically evaluated. Another dynamic process could be studied, for the first time in this kind of compounds.
- Kleinpeter, Erich,Werner, Peter,Linker, Torsten
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p. 3801 - 3809
(2017/06/13)
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- A Pd/Monolayer Titanate Nanosheet with Surface Synergetic Effects for Precise Synthesis of Cyclohexanones
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A catalyst composed of monolayer nonstoichiometric titanate nanosheets (denoted as TN) and Pd clusters is constructed for precise synthesis of cyclohexanone from phenol hydrogenation with high conversion (>99%) and selectivity (>99%) in aqueous media under light irradiation. Experimental and DFT calculation results reveal that the surface exposed acid and basic sites on TN could interact with phenol molecules in a nonplanar fashion via a hexahydroxy hydrogen-bonding ring to form a surface coordination species. This greatly facilitates the adsorption and activation of phenol molecules and suppresses the further hydrogenation of cyclohexanone. Moreover, the surface Pd clusters serve as the active sites for the adsorption and dissociation of hydrogen molecules to provide active H atoms. The synergistic effect of the surface coordination species, TN and Pd clusters remarkably facilitate the high yield of cyclohexanone in photocatalysis. Finally, the possible thermo/photocatalytic mechanisms on Pd/TN are proposed. This work not only highlights the great potential for monolayer nonstoichiometric composition nanosheets in the construction of catalysts for precise organic synthesis but also provides insight into the inherent catalytic behavior at a molecular level.
- Song, Yujie,Wang, Hao,Gao, Xiaomei,Feng, Yingxin,Liang, Shijing,Bi, Jinhong,Lin, Sen,Fu, Xianzhi,Wu, Ling
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p. 8664 - 8674
(2017/12/08)
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- Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction
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An efficient desymmetrizing carbonyl-ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N′-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol methodology originates from the efficient interaction between the catalyst with enophiles, discrimination of the two chair conformations of olefinic components, and the intrinsic six-membered transition-state structure of ene process.
- Luo, Weiwei,Lin, Lili,Zhang, Yu,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 3374 - 3377
(2017/07/15)
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- FeCl3·6H2O/acetaldehyde, a versatile system for the deprotection of ketals and acetals via a transacetalization process
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Mild and efficient catalytic deprotection of ketals/acetals mediated by FeCl3·6H2O/acetaldehyde has been described in this paper. The versatility and high chemoselectivity of the iron(iii)/aldehyde system are demonstrated by a large scope of examples. Deprotected ketones/aldehydes are nearly quantitatively isolated after filtration over a pad of silica gel followed by evaporation of volatile by-products.
- Schiavo, Lucie,Jeanmart, Lo?c,Lanners, Steve,Choppin, Sabine,Hanquet, Gilles
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p. 1421 - 1424
(2017/02/23)
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- Robustly supported rhodium nanoclusters: Synthesis and application in selective hydrogenation of lignin derived phenolic compounds
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The stabilization of small rhodium nanoclusters (NCs) in a polymer derived silicon carbonitride (SiCN) matrix has been reported to generate highly robust and active solid catalysts for the selective hydrogenation of phenolic compounds. An aminopyridinato Rh complex was used to modify a preceramic polymer (HTT 1800) followed by its pyrolysis at 1100 °C to afford small Rh NCs nicely dispersed over dense SiCN ceramic. For the synthesis of porous catalysts containing Rh NCs, microphase separation (followed by pyrolysis) of a diblock copolymer of HTT 1800 with hydroxy-polyethylene (PE-OH) was used. Both catalysts exhibit high activity in the hydrogenation of substituted phenols at room temperature and under low hydrogen pressure. The catalysts remained highly active and selective for six consecutive catalytic runs.
- Fehn, Sonja,Zaheer, Muhammad,Denner, Christine E.,Friedrich, Martin,Kempe, Rhett
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p. 9252 - 9256
(2016/11/11)
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- Pd/TiN nanocomposite catalysts for selective hydrogenation of phenol and its derivatives
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Pd/TiN nanocomposite catalysts were fabricated for one-step selective hydrogenation of phenol to cyclohexanone successfully. High conversion of phenol (99%) and selectivity of cyclohexanone (98%) were obtained at 30?°C and 0.2?MPa H2for 12?h in the mixed solvents of H2O and CH2Cl2. The Pd nanoparticles were stable in the reaction, and no aggregation was detected after four successive runs. The catalytic activity and selectivity depended on slightly the Pd particle sizes. The generality of the catalysts for this reaction was demonstrated by the selective hydrogenation of phenol derivatives, which showed that the catalyst was selective for the formation of cyclohexanone.
- Li, Hai-Feng,Zhang, Qin-Sheng,Pang, Zeng-Bo,Tian, Mi,Gao, Ping,Wang, Lai-Lai
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p. 1500 - 1504
(2016/09/23)
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- Post-synthesized zirconium-containing Beta zeolite in Meerwein-Ponndorf-Verley reduction: Pros and cons
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Zr-Beta zeolite was prepared by a two-step post-synthesis method involving dealumination of Al-Beta followed by wet impregnation with Zr(NO3)4. Compared with Zr-Beta formed under fluoride-mediated hydrothermal conditions, the post-synthesized samples had smaller particle size and stronger Lewis acidity. The materials were tested as catalysts for Meerwein-Ponndorf-Verley reduction. In the reduction of 4-tert-butylcyclohexanone, it exhibited the same excellent stereoselectivity toward cis-4-tert-butylcyclohexanol (>99%) as the HF-synthesized Zr-Beta, but had a lower TOF. Because of the higher density of zirconium sites and the nanosized crystallites, it was a more effective catalyst for the MPV reduction of 1,4-cyclohexanedione, bulky aldehydes and aromatic ketones. However, it is more susceptible to poisoning by water adsorption because of its hydrophilic nature. The easily scalable synthesis method allows a faster preparation of metal-substituted Lewis acid zeolites, although differences in textural and chemical properties should be taken into consideration when the material is applied as a catalyst.
- Wang, Jie,Okumura, Kazu,Jaenicke, Stephan,Chuah, Gaik-Khuan
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p. 112 - 120
(2015/09/28)
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- Efficient room-temperature aqueous-phase hydrogenation of phenol to cyclohexanone catalyzed by Pd nanoparticles supported on mesoporous MMT-1 silica with unevenly distributed functionalities
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Efficient and selective aqueous-phase hydrogenation of phenol by a novel Pd catalyst supported on dually and selectively functionalized mesoporous MMT-1 silica nanoparticles has been developed. The catalyst features small (～1.1 nm) Pd nanoparticles surrounded by unevenly distributed nitrogen- or heteroatom-free organic groups in the helical mesopores and the presence of non-hydrogen-bonded isolated silanol groups on the mesopore surface. The catalyst exhibited superior conversion of phenol and high selectivity of cyclohexanone at room temperature under atmospheric pressure of hydrogen and remained highly active after ten catalytic runs. The catalyst was active for the aqueous-phase hydrogenation of a variety of mono- and dihydroxylated aromatic compounds. The green protocol with the designed catalyst would be practical for the hydrogenation of phenol and other derivatives.
- Lin, Chi-Jui,Huang, Shao-Hsien,Lai, Nien-Chu,Yang, Chia-Min
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p. 4121 - 4129
(2015/11/11)
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- Selective hydrogenation of phenol to cyclohexanone in water over PD@N-doped carbon derived from ionic-liquid precursors
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In this report, a kind of mesoporous N-doped carbon (CN-x) derived from N-containing ionic-liquid (IL) precursors were synthesized, and Pd@CN-x prepared by a simple ultrasound-assisted method showed higher catalytic activity for the selective hydrogenation of phenol and its derivatives under mild reaction conditions in water than commercial Pd@C and other common Pd heterogeneous catalysts. The catalytic activities of Pd@CN-x derived from different ILs were different, and further study into the influencing factors, including physical properties, N species of CN-x, and Pd status of Pd@CN-x, were performed. Being picky: N-Doped carbon (CN-x) derived from N-containing ionic-liquid precursors are used as Pd nanoparticle supports for the selective hydrogenation of phenol to cyclohexanone with high activity and selectivity under mild reaction conditions. The activities of the Pd@CN-x catalysts derived from a variety of ionic liquids are different, and studies on the physical properties, Pd status, and N species of the catalysts are performed.
- Xu, Xuan,Li, Haoran,Wang, Yong
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p. 3328 - 3332
(2015/04/16)
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- Selective Hydrogenation of Phenol to Cyclohexanone over Pd-HAP Catalyst in Aqueous Media
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The production of pure cyclohexanone under mild conditions over catalysts with high reactivity, selectivity, compatibility, stability, and low cost is still a great challenge. Here we report a hydroxyapatite-bound palladium catalyst (Pd-HAP) to demonstrate its excellent performance on phenol hydrogenation to cyclohexanone. Based on catalyst characterization, the Pd nanoclusters (≈0.9 nm) are highly dispersed and bound to phosphate in HAP. Only basic active sites on HAP surface are detected. At 25°C and ambient H2 pressure in water, phenol can be 100% converted into cyclohexanone with 100% selectivity. This system shows a universal applicability to temperature, pH, solvent, low H2 purity, and pressure. The catalyst reveals high stability to be recycled without deactivation or morphology change; and Pd nano-clusters barely aggregate even at 400°C. During the reaction, HAP adsorbs phenol, and Pd nanoclusters activate and spillover H2. The mechanism is also investigated, proposed, and verified.
- Xu, Guangyue,Guo, Jianhua,Zhang, Ying,Fu, Yao,Chen, Jinzhu,Ma, Longlong,Guo, Qingxiang
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p. 2485 - 2492
(2015/08/24)
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- Regio- and enantioselective reduction of diketones: Preparation of enantiomerically pure hydroxy ketones catalysed by Candida parapsilosis ATCC 7330
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Enantiomerically enriched hydroxy ketones were prepared by the reduction of the corresponding diketones with excellent enantiomeric excess (98%) and in good yields (up to 75%) using whole cells of Candida parapsilosis ATCC 7330. Cyclic diketones, such as 1,2-cyclohexanedione and 1,4-cyclohexanedione, resulted in hydroxy ketones as products. Cyclohexane-1,3-dione and 5,5-dimethylcyclohexane-1,3-dione gave dimerised products, such as 2,2′-(ethane-1,1-diyl)bis(3-hydroxycyclohex-2-enone) and 2,2′-(ethane-1,1-diyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) with acetaldehyde generated in situ from whole cells of Candida parapsilosis ATCC 7330, which is reported here for the first time.
- Mahajabeen, Pula,Chadha, Anju
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p. 1167 - 1173
(2015/10/28)
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- Preparation, characterization and catalytic activity of MgO/SiO2 supported vanadium oxide based catalysts
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Vanadium oxide-based catalyst obtained by grafting VOCl3 on Florisil (MgO:SiO2) with the molar ratio of 15:85 have been studied for the selective oxidation of cyclohexane in order to obtain cyclohexyl hydroperoxide, cyclohexanol and
- Aboelfetoh, Eman Fahmy,Pietschnig, Rudolf
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- Highly selective hydrogenation of phenol and derivatives over Pd catalysts supported on SiO2 and γ-Al2O3 in aqueous media
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Pd/Al2O3 and Pd/SiO2 catalysts containing Pd nanoparticles in the size range of 3-13 nm were prepared and investigated in direct selective hydrogenation of phenol to cyclohexanone. Catalysts with 3 nm Pd nanoparticles present highly active and promoted the selective formation of cyclohexanone under atmospheric pressure of hydrogen in aqueous media without additives. Conversion of 99% and a selectivity higher than 99% were achieved within 3 h at 333 K. The generality of Pd/Al2O3 catalyst with 3 nm Pd nanoparticles for this reaction was demonstrated by selective hydrogenation of other hydroxylated aromatic compounds with similar performance.
- Cheng, Ling,Dai, Qiguang,Li, Hua,Wang, Xingyi
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- Discovery of spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amines as potent NOP and opioid receptor agonists
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We report the discovery of spiro[cyclohexane-pyrano[3,4-b]indole]-amines, as functional nociceptin/orphanin FQ peptide (NOP) and opioid receptor agonists with strong efficacy in preclinical models of acute and neuropathic pain. Utilizing 4-(dimethylamino)-4-phenylcyclo-hexanone 1 and tryptophol in an oxa-Pictet-Spengler reaction led to the formation of spiroether 2, representing a novel NOP and opioid peptide receptor agonistic chemotype. This finding initially stems from the systematic derivatization of 1, which resulted in alcohols 3-5, ethers 6 and 7, amines 8-10, 22-24, and 26-28, amides 11 and 25, and urea 12, many with low nanomolar binding affinities at the NOP and mu opioid peptide (MOP) receptors.
- Schunk, Stefan,Linz, Klaus,Frormann, Sven,Hinze, Claudia,Oberb?rsch, Stefan,Sundermann, Bernd,Zemolka, Saskia,Englberger, Werner,Germann, Tieno,Christoph, Thomas,K?gel, Babette-Y.,Schr?der, Wolfgang,Harlfinger, Stephanie,Saunders, Derek,Kless, Achim,Schick, Hans,Sonnenschein, Helmut
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p. 851 - 856
(2014/09/17)
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- Microwave-assisted oxidation of alcohols using zinc polyoxometalate
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In the presence of 30% aqueous hydrogen peroxide and [WZn3(H2O)2][ZnW9O34)2]12- polyoxometalate as a catalyst, primary and secondary alcohols were oxidized to carboxylic acids and ketones, respectively, in short reaction times (ca. 15 min) under microwave-pressurized conditions.
- Kasprzyk, Wiktor,Galica, Mateusz,Bednarz, Szczepan,Bogda?, Dariusz
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supporting information
p. 2757 - 2760
(2015/02/02)
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- OXAZOLIDINONE COMPOUNDS AND DERIVATIVES THEREOF
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Compounds of Formula (I) and Formula (II) are useful inhibitors of tankyrase. Compounds of Formula (I) and Formula (II) have the following structure: where the definitions of the variables are provided herein.
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Paragraph 0219-0220
(2013/09/26)
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- Chemoenzymatic asymmetric synthesis of serotonin receptor agonist (R)-frovatriptan
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A simple chemoenzymatic asymmetric route has been developed for the production of antimigraine agent (R)-Frovatriptan. Lipases and oxidoreductases have been identified as ideal biocatalysts for the production of enantiopure adequate synthetic intermediates under safe and environmentally friendly conditions. (S)-3-Hydroxy-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile, an optimal building block for the synthesis of the drug, has been efficiently prepared through Candida antarctica lipase type B catalyzed acylation of its corresponding racemic mixture or alcohol dehydrogenase A mediated bioreduction of the corresponding ketone. The inversion of the chiral center has been identified as a key step, optimizing the process to avoid partial racemization. Finally, amine functionalization and nitrile hydrolysis have allowed the production of (R)-Frovatriptan in enantiomerically pure form. A simple chemoenzymatic preparation has been developed for the production of serotonin receptor agonist (R)-Frovatriptan starting from inexpensive starting materials. The enzymatic action towards ketone or alcohol intermediates is the key step for the asymmetric total synthesis of this drug. Copyright
- Busto, Eduardo,Martinez-Montero, Lia,Gotor, Vicente,Gotor-Fernandez, Vicente
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p. 4057 - 4064
(2013/07/26)
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- Reactivity of C-H bonds in cyclohexanone and 1-tert-butylperoxycyclohexanol toward the tert-butylperoxyl radical
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The kinetics of oxygen uptake and the composition of the cyclohexanone oxidation products in the azobisisobutyronitrile-initiated oxidation of cyclohexanone in the presence of tert-butyl hydroperoxide have been investigated by the Howard-Ingold method. The partial rate constants of the reaction of the tert-butylperoxyl radical with the C-H bonds of cyclohexanol and 1-tert-butylperoxycyclohexanole at 333 K have been determined. The carbonyl group of cyclohexanone activates the C-H bonds in the 2- and 6-positions (α) and deactivates the C-H bonds in the 3- and 5-positions (β) compared to the C-H bonds in the 4-position (γ), whose reactivity is similar to that of the methylenic C-H bonds in cyclohexane. Evaluation of the joint effect of the hydroxyl and tert-butylperoxyl groups in 1-tert-butylperoxycyclohexanol suggests a considerable deactivation of the C-H bonds in the 2- and 6-positions (β) and, to a lesser extent, in the 3- and 5-positions (γ).
- Puchkov,Nepomnyashchikh,Kozlova,Perkel
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p. 139 - 148
(2013/06/26)
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- Synthesis and NMR spectroscopic conformational analysis of esters of 4-hydroxy-cyclohexanone - The more polar the molecule the more stable the axial conformer
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The esters of 4-hydroxy-cyclohexanone and a series of carboxylic acids R-COOH with R of different electronic and steric influence (R=Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, sec-Bu, t-Bu, CF3, CH2Cl, CHCl 2, CCl3, CH2Br, CHBr2, and CBr 3) were synthesized and the conformational equilibria studied by 1H and 13C NMR spectroscopy at 103 K and at 295 K, respectively. The geometry of optimized structures of the axial/equatorial chair conformers was computed at the ab initio MO and DFT levels of theory. Only one preferred conformation was obtained for the axial and the equatorial conformer as well. When comparing the conformational equilibria of the cyclohexanone esters with those of the corresponding cyclohexyl esters a certain polarity contribution of the cyclohexanone framework was revealed, which is independent of the substituent effects and increases the stability of the axial conformers by a constant amount.
- Kleinpeter, Erich,Heydenreich, Matthias,Koch, Andreas,Linker, Torsten
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experimental part
p. 2363 - 2373
(2012/04/17)
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- High-performance gold-promoted palladium catalyst towards the hydrogenation of phenol with mesoporous hollow spheres as support
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A high-performance, gold-promoted Pd catalyst with mesoporous hollow silica spheres as support, PdAu/MHSS, was prepared using an impregnation-reduction approach. The catalyst showed 10 times higher activity than commercial Pd/C catalyst and 6 times higher activity than Pd/MHSS catalyst. The conversion of phenol was 100% within 30 min of reaction at 80 °C. The catalyst was characterized by XRD, XPS, and TEM, which revealed that its high performance may result from both the high dispersion of active components on the MHSS, caused by the addition of gold, and the interaction between palladium and gold.
- Yang, Xu,Du, Li,Liao, Shijun,Li, Yuexia,Song, Huiyu
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scheme or table
p. 29 - 33
(2012/03/26)
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- Synthesis and properties of isomerically pure anthrabisbenzothiophenes
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The synthesis of three heptacyclic heteroacenes is described, namely anthra[2,3-b:7,6-b′]bis[1]benzothiophenes (ABBTs). A stepwise sequence of aldol reactions provides regiochemical control, affording only the syn-isomer. The ABBTs are characterized by X-ray crystallography, UV-vis absorption, and emission spectroscopy, as well as cyclic voltammetry. Field effect transistors based on solution-cast thin films of ABBT derivatives exhibit charge-carrier mobilities of as high as 0.013 cm2/(V s).
- Lehnherr, Dan,Hallani, Rawad,McDonald, Robert,Anthony, John E.,Tykwinski, Rik R.
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- Highly selective hydrogenation of phenol and derivatives over a pd@carbon nitride catalyst in aqueous media
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Cyclohexanone is an important intermediate in the manufacture of polyamides in chemical industry, but direct selective hydrogenation of phenol to cyclohexanone under mild conditions is a challenge. We report here a catalyst made of Pd nanoparticles supported on a mesoporous graphitic carbon nitride, Pd@mpg-C3N4, which was shown to be highly active and promoted the selective formation of cyclohexanone under atmospheric pressure of hydrogen in aqueous media without additives. Conversion of 99% and a selectivity higher than 99% were achieved within 2 h at 65 °C. The reaction can be accelerated at higher temperature, but even at room temperature, 99% conversion and 96% selectivity could still be obtained. The generality of the Pd@mpg-C 3N4 catalyst for this reaction was demonstrated by selective hydrogenation of other hydroxylated aromatic compounds with similar performance.
- Wang, Yong,Yao, Jia,Li, Haoran,Su, Dangsheng,Antonietti, Markus
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supporting information; experimental part
p. 2362 - 2365
(2011/05/04)
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- A tuneable bifunctional water-compatible heterogeneous catalyst for the selective aqueous hydrogenation of phenols
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A water-tolerant bifunctional heterogeneous catalyst is able to effectively catalyse the selective hydrogenation of phenol to cyclohexanone in water at atmospheric pressure and room temperature with >99.9% selectivity to cyclohexanone at phenol conversions >99.9%. The catalyst was found to be highly active and reusable, giving identical activities and selectivities after >5 uses. Moreover, this reported simple bifunctional catalyst is also able to hydrogenate a range of substituted phenols in high yields under the investigated aqueous conditions. Copyright
- Liu, Hongli,Li, Yingwei,Luque, Rafael,Jiang, Huanfeng
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supporting information; experimental part
p. 3107 - 3113
(2012/01/02)
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- PICOLINAMIDE AND PYRIMIDINE-4-CARBOXAMIDE COMPOUNDS, PROCESS FOR PREPARING AND PHAMACEUTICAL COMPOSITION COMPRISING THE SAME
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Provided are picolinamide and pyrimidine-4-carboxamide compounds, a method for preparing the same, a pharmaceutical composition containing the same, and a medical use using the compound as an agent for preventing, regulating, and treating diseases related to regulation of glucocorticoids by using selective inhibitory activity of the compound for an 11β-HSD1 enzyme. The picolinamide and pyrimidine-4-carboxamide compounds of the present invention are selective inhibitors of human-derived 11β-HSD1 enzymes, and are useful in an agent for preventing, regulating, and treating diseases related to glucocorticoid regulation in which human- derived 11β-HSD1 enzymes are involved, for example, metabolic syndromes such as, type 1 and type 2 diabetes, diabetes later complications, latent autoimmune diabetes adult (LAD A), insulin tolerance syndromes, obesity, impaired glucose tolerane (IGT), impaired fasting glucose (IFG), damaged glucose tolerance, dyslipidemia, atherosclerosis, hypertension, etc.
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Page/Page column 89
(2011/11/30)
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- Novel Compounds for the Treatment of Diseases Associated with Amyloid or Amyloid-Like Proteins
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The present invention relates to novel compounds that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein, such as Alzheimer's disease, and of diseases or conditions associated with amyloid-like proteins. The compounds of the present invention can also be used in the treatment of ocular diseases associated with pathological abnormalities/changes in the tissues of the visual system. The present invention further relates to pharmaceutical compositions comprising these compounds and to the use of these compounds for the preparation of medicaments for treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins. A method of treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins is also disclosed.
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- Hydrogenation of phenol in supercritical carbon dioxide catalyzed by palladium supported on Al-MCM-41: A facile route for one-pot cyclohexanone formation
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The hydrogenation of phenol has been carried out in supercritical carbon dioxide (scCO2) under very mild reaction conditions at the temperature of 50°C over palladium supported Al-MCM-41 (metal loading ～1%). This palladium catalyst is shown to be highly active and promotes the selective formation of cyclohexanone (～98%), an industrially important compound, in a "one-pot～ way. The effects of different variables like carbon dioxide and hydrogen pressure, reaction time and also silica/alumina ratio of the MCM-41 support along with palladium dispersion are presented and discussed. The pressure effect of carbon dioxide is significantly prominent in terms of conversion and cyclohexanone selectivity. Moreover, the silica/alumina ratio was also found to be an important parameter to enhance the effectiveness of the catalyst as it exhibits a remarkable increase in phenol conversion from 20.6% to 98.4% as the support changes from only silica MCM-41 to Al-MCM-41. A plausible mechanism for the hydrogenation of phenol to cyclohexanone over the palladium catalyst has been proposed. The proposition is vali-dated by transition state calculations using density functional theory (DFT), which reveal that cyclohexanone is a favorable product and stabilized by -1 over cyclohexanol in ScCO2 medium. Under similar reaction conditions, phenol hydrogenation was also carried out with rhodium, supported on Al-MCM-41. In contrast to the palladium catalyst, a mixture of cyclohexanone (57.8%) and cyclohexanol (42.2%) was formed. Detailed characterization by X-ray diffraction and transmission electron microscopy confirmed the presence of metal nanoparticles (palladium and rhodium) between 10-20 nm. Both the catalysts exhibit strikingly different product distributions in solventless conditions compared to scCO2. This method can also be successfully applied to the other hydroxylated aromatic compounds.
- Chatterjee,Kawanami,Sato,Chatterjee,Yokoyama,Suzuki
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experimental part
p. 1912 - 1924
(2011/03/17)
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- A broadly applicable mild method for the synthesis of gem-diperoxides from corresponding Ketones or 1,3-dioxolanes
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Ketones or ketals were readily converted into the corresponding gem-dihydroperoxides in high yields by treatment with ethereal H 2O2 at ambient temperature in the presence of 2-5 mol % of phosphomolybdic acid.
- Li, Yun,Hao,Zhang, Qi,Wu, Yikang
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body text
p. 1615 - 1618
(2009/08/07)
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- Synthesis and identification of hydroxylated metabolites of the anti-estrogenic agent cyclofenil
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The detection of metabolites of the anti-estrogenic substance cyclofenil, listed on the World Anti-Doping Agency (WADA) Prohibited List since 2004 is described. Target substances are hydroxylated metabolites, bearing an aliphatic hydroxyl group either in the 2-, 3- or 4-position of the aliphatic ring, in addition to the phenolic functions on the aromatic rings. Structural identification used NMR as well as high-resolution mass spectrometry after nano-electrospray ionisation (ESI). Unambiguous detection of all three synthesised cyclofenil metabolites M1-M3 was done using gas chromatography for separation and electron ionisation mass spectrometry for detection of the per-silylated compounds in comparison with a reference urine deriving from an excretion study within the WADA 2007 Educational Programme. Copyright
- Gaertner, Peter,Hofbauer, Karin,Reichel, Christian,Geisendorfer, Thomas,Gmeiner, Guenter
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experimental part
p. 958 - 964
(2009/05/07)
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- Selective partial hydrogenation of hydroxy aromatic derivatives with palladium nanoparticles supported on hydrophilic carbon
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Selective hydrogenation of phenol to cyclohexanol in the aqueous phase was achieved using a new catalytic system based on palladium particles supported on hydrophilic carbon prepared by one-pot hydrothermal carbonisation. The Royal Society of Chemistry.
- Makowski, Philippe,Demir Cakan, Rezan,Antonietti, Markus,Goettmann, Frederic,Titirici, Maria-Magdalena
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p. 999 - 1001
(2008/09/21)
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- Oligospiroketals as novel molecular rods
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A modular approach for the synthesis of molecular rods based on oligospiroketals has been developed. The strategy relies on different terminal and intermediate segments, which are joined by ketal formation between ketones and diols. For this purpose it was necessary to develop a new ketalization method to circumvent some problems related with the established methods. The terminal segments are either derived from 4-piperidinone or from 4-oxocyclohexane carboxylic acid whereas the intermediate segments rest on pentaerythritol and cyclohexane-1,4-dione. A series of trispiro (14-18), hexaspiro (19) and nonaspiro (20) compounds have been prepared and characterized. From these we realized that it is imperative to use solubility enhancing groups if more than seven rings are joined.
- Wessig, Pablo,Moellnitz, Kristian,Eiserbeck, Christiane
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p. 4859 - 4872
(2008/02/03)
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- METHOD FOR PRODUCTION OF 1,6-HEXANEDIOL WITH A PURITY IN EXCESS OF 99.5 %
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The invention relates to a method for the production of 1,6-hexanediol by hydrogenation of ester mixtures of dialkyl adipates and alkyl 6-hydroxycaproates, containing 1,4-cyclohexanedione and 4-hydroxycyclohexan-1-one as impurities, by a) removing excess alcohol and low-boilers from the obtained ester mixture in a first distillation stage (alcohol removal) b) separation of the sump product into an ester fraction essentially free of 1,4-cyclohexanediols and a fraction containing at least the greater part of the 1,4-cyclohexanediols in a second distillation stage, c) catalytic hydrogenation of the ester fraction essentially free of 1,4-cyclohexanediols (ester hydrogenation) and d) isolation of 1,6-hexanediol from the hydrogenation product in a known manner by a simple distillation step, characterised in that, before step a) and/or before step b), the ester mixture is selectively hydrogenated (purification hydrogenation).
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Page/Page column 8
(2008/06/13)
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- Clean and selective oxidation of alcohols catalyzed by ion-supported TEMPO in water
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Three different types of ion-supported TEMPO catalysts are synthesized and their catalytic activity in the chemoselective oxidation of alcohols is investigated. These new catalysts show high catalytic activity in water and can be reused for the next run by extraction of products. Recycling experiments exhibit that ion-supported TEMPO can be reused up to five times without loss of catalytic activity. This system offers a very clean, convenient, environmentally benign method for the selective oxidation of alcohols.
- Qian, Weixing,Jin, Erlei,Bao, Weiliang,Zhang, Yongmin
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p. 556 - 562
(2007/10/03)
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- Fluorine-substituted cyclofenil derivatives as estrogen receptor ligands: Synthesis and structure-affinity relationship study of potential positron emission tomography agents for imaging estrogen receptors in breast cancer
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In a search for estrogen receptor (ER) ligands to be radiolabeled with fluorine-18 for imaging of ER-positive breast tumors with positron emission tomography (PET), we investigated cyclofenil analogues substituted at the C3 or C4 position of the cyclohexyl group. McMurry coupling of 4,4′- dihydroxybenzophenone with various ketones produced key cyclofenil intermediates, from which C3 and C4 substituents containing alkyl and various oxygen or fluorine-substituted alkyl groups were elaborated. Binding assays to both ERα and ERβ revealed that the C3 site is more tolerant of steric bulk and polar groups than the C4 site, consistent with a computational model of the ERα ligand binding pocket. Fluorine substitution is tolerated very well at some sites, giving some compounds having affinities comparable to or higher than that of estradiol. These fluoro and fluoroalkyl cyclofenils merit further consideration as fluorine-18 labeled ER ligands for PET imaging of ERs in breast tumors.
- Seo, Jai Woong,Comninos, John S.,Chi, Dae Yoon,Kim, Dong Wook,Carlson, Kathryn E.,Katzenellenbogen, John A.
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p. 2496 - 2511
(2007/10/03)
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- New bioorganic reagents: Evolved cyclohexanone monooxygenase - Why is it more selective?
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Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.
- Kayser, Margaret M.,Clouthier, Christopher M.
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p. 8424 - 8430
(2007/10/03)
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- Synthesis of the tetronate-containing core structure of the antibiotic abyssomicin C
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The core structure of abyssomicin C (1) containing an oxabicyclooctanone ring and a tetronate was prepared from the addition product of lithium ethyl propiolate and 4-tert-butyldimethylsilyloxycyclohexanone. Tetronate formation via addition of sodium methanolate followed by hydrolysis gave the hydroxy tetronic acid 27. The spiro compound 27 could be cyclized to the tricyclic tetronate 23 by a transannular Mitsunobu lactonization. Alternatively, 27 could be prepared from the cyanohydrin cis-19.
- Rath, Jean-Philippe,Eipert, Martin,Kinast, Stephan,Maier, Martin E.
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p. 314 - 318
(2007/10/03)
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- Phosphoryl choline coating compositions
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A polymer comprising phospholipid moieties and a biocompatible polymer backbone, a composition comprising the polymer and optionally a bioactive agent, an implantable devices such as a DES comprising thereon a coating comprising the polymer and optionally a bioactive agent, and a method of using the device for the treatment of a disorder in a human being are provided.
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Page/Page column 8
(2010/02/14)
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- Protection of the carbonyl group as 1,2,4-trioxane and its regeneration under basic conditions
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(Chemical Equation Presented) An experimental protocol demonstrating the protection of the carbonyl group as 1,2,4-trioxane, the stability of the protecting group under a variety of reaction conditions, and the regeneration of the carbonyl group with Triton B in THF at room temperature is presented. The method provides a useful alternative for the protection of carbonyl compounds having acid-sensitive moieties.
- Singh, Chandan,Malik, Heetika
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p. 5673 - 5676
(2007/10/03)
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- Synthesis of agarofuran antifeedants. Part 6: Enantioselective synthesis of a key decalinic intermediate
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The asymmetric synthesis of a template decalin precursor in the synthesis of polyhydroxylated agarofuran sesquiterpenes is described via a Lewis acid catalysed addition of furan to an activated cyclohexenone directed by an adjacent chiral ketal moiety.
- Boyer, Francois-Didier,Prange, Thierry,Ducrot, Paul-Henri
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p. 1153 - 1159
(2007/10/03)
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- Mild and chemoselective catalytic deprotection of ketals and acetals using cerium(IV) ammonium nitrate
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Cerium(IV) ammonium nitrate (CAN) is a powerful, though mild, reagent for the efficient and selective removal of a range of ketals and acetals. This novel deprotection method requires only catalytic amounts of CAN and tolerates a variety of functional and protecting groups. Mechanistic insights suggest that the Ce(IV) salts act as unique Lewis acids and not as redox active species.
- Ates, Ali,Gautier, Arnaud,Leroy, Bernard,Plancher, Jean-Marc,Quesnel, Yannick,Vanherck, Jean-Christophe,Markó, István E.
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p. 8989 - 8999
(2007/10/03)
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