101-39-3Relevant articles and documents
IBX-TfOH mediated oxidation of alcohols to aldehydes and ketones under mild reaction conditions
Kumar, Kamlesh,Kumar, Prashant,Joshi, Penny,Rawat, Diwan S
, (2020)
An efficient, practical and facile procedure has been developed for the oxidation of primary and secondary alcohols using IBX-TfOH catalytic system in 1,4-dioxane at ambient temperature. The reaction affords quantitative yields of the corresponding carbonyl compounds without the formation of over oxidized products. The present synthetic protocol is compatible with a variety of substrates having arene, heteroarene and alkene functionalities. The developed synthetic protocol can be used for higher scale reactions as evident by the oxidation of alcohol at 1 g scale in higher yields by a simple filtration process.
Pd-nanoparticles stabilized by pyridine-functionalized poly(ethylene glycol) as catalyst for the aerobic oxidation of α,β-unsaturated alcohols in water
Giachi, Guido,Oberhauser, Werner,Frediani, Marco,Passaglia, Elisa,Capozzoli, Laura,Rosi, Luca
, p. 2518 - 2526 (2013)
The synthesis and coordination chemistry of 4-pyridinemethylene end-capped MeO-PEG (LPy) to Pd(II) was investigated. The PEG-based macroligand LPy was straightforwardly synthesized by pyridine end-functionalization of PEG monomethyl ether and employed to stabilize Pd(II) in a neutral (1a) and bis-cationic (2a) macrocomplex, characterized by a LPy to Pd molar ratio of 2 and 4, respectively. The homogeneous distribution of the Pd-NPs in 2b exerted a significant stabilizing effect on the poly(ether) chain of LPy against its oxidative thermal degradation. From a screening of the Pd(II)- and Pd-NP-based catalysts in the aerobic oxidation of unsaturated alcohols in water emerged 2b as the most stable catalyst, showing TOF-values up to 200-h and high chemoselectivity even for prolonged reaction times.
Design and synthesis of chitin synthase inhibitors as potent fungicides
Chen, Qi,Zhang, Ji-Wei,Chen, Lu-Lu,Yang, Jun,Yang, Xin-Ling,Ling, Yun,Yang, Qing
, p. 1232 - 1237 (2017)
Chitin is a structural component of fungal cell walls but is absent in vertebrates, mammals, and humans. Chitin synthase is thus an attractive molecular target for developing fungicides. Based on the structure of its donor substrate, UDP-N-acetyl-glucosamine, as well as the modelled structure of the bacterial chitin synthase NodC, we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors. The most potent inhibitor, compound 13, exhibited high chitin synthase inhibitory activity with an IC50 value of 64.5?μmol/L. All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi, Fusarium graminearum, Botrytis cinerea, and Colletotrichum lagenarium. This work presents a new scaffold which can be used for the development of novel fungicides.
Reaction-driven surface restructuring and selectivity control in allylic alcohol catalytic aerobic oxidation over Pd
Lee, Adam F.,Ellis, Christine V.,Naughton, James N.,Newton, Mark A.,Parlett, Christopher M. A.,Wilson, Karen
, p. 5724 - 5727 (2011)
Synchronous, time-resolved DRIFTS/MS/XAS cycling studies of the vapor-phase selective aerobic oxidation of crotyl alcohol over nanoparticulate Pd have revealed surface oxide as the desired catalytically active phase, with dynamic, reaction-induced Pd redox processes controlling selective versus combustion pathways.
Method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde
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Paragraph 0011; 0051-0059, (2021/03/31)
The invention discloses a method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde. The method comprises the following steps: 1) under the catalysis of alkali liquor, enabling phenylpropionaldehyde and an aqueous formaldehyde solution to pass through a continuous tank reactor, and conducting condensing to obtain a 2-benzylacrolein intermediate; and 2) carrying out hydroisomerization to obtain alpha-methylcinnamaldehyde. The raw materials, namely phenylpropionaldehyde and formaldehyde selected in the method are widely and readily available and low in price, so the method has a cost advantage; and the formaldehyde has good water solubility, the phenylpropionaldehyde is not easy to undergo the Cannizaro side reaction, and the intermediate prepared by condensation of the phenylpropionaldehyde and the phenylpropionaldehyde is easy to realize high yield.
Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
Aleku, Godwin A.,Leys, David,Roberts, George W.
, p. 3927 - 3939 (2020/07/09)
We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
Pd-Catalyzed Carbonylation of Vinyl Triflates to Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions
Zhang, Shaoke,Neumann, Helfried,Beller, Matthias
, p. 3528 - 3532 (2019/05/24)
An efficient and general protocol for the synthesis of α,β-unsaturated aldehydes, esters, and amides via carbonylation of vinyl triflates including derivatives of camphor, ketoisophorone, verbenone, and pulegone was developed. Crucial for these transformations is the use of a specific palladium catalyst containing a pyridyl-substituted dtbpx-type ligand. This procedure also allows for an easy access of dicarbonylated products from the corresponding ketones.
CO2-Catalyzed oxidation of benzylic and allylic alcohols with DMSO
Riemer, Daniel,Mandaviya, Bhavdip,Schilling, Waldemar,G?tz, Anne Charlotte,Kühl, Torben,Finger, Markus,Das, Shoubhik
, p. 3030 - 3034 (2018/04/14)
CO2-catalyzed transition-metal-free oxidation of alcohols has been achieved. Earlier, several methodologies have been explored for alcohol oxidations based on transition-metal catalysts. However, owing to the cheaper price, easy separation and nontoxicity, transition-metal-free systems are in high demand to the pharmaceutical industries. For this reason, various primary and secondary alcohols have been selectively oxidized to the corresponding carbonyl compounds using CO2 as a catalyst in the presence of different functional groups such as nitrile, nitro, aldehyde, ester, halogen, ether, and so on. At the end, transition-metal-free syntheses of pharmaceuticals have also been achieved. Finally, the role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments and DFT calculations.
Fe(NO3)3/2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ): An efficient catalyst system for selective oxidation of alcohols under aerobic conditions
Hu, Yongke,Chen, Lei,Li, Bindong
, p. 42 - 46 (2017/10/05)
A practical and efficient catalyst system for the oxidation of alcohols to carbonyl compounds using catalytic amounts of DDQ and Fe(NO3)3 with air as the environmentally benign oxidant has been developed. A variety of benzylic, heterocyclic, allylic and propargylic alcohols were smoothly converted into aldehydes or ketones in good to excellent yields. In case of large-scale reaction for the oxidation of benzyl alcohol, benzaldehyde was obtained in 93% isolated yield. Moreover, a possible reaction mechanism was proposed.
A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes
Vrbková, Eva,Vysko?ilová, Eli?ka,Rott, Martin,Zapletal, Martin,?erveny, Libor
, p. 2603 - 2613 (2017/03/22)
The 4-Alkyl-α-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-α-methylcinnamylaldehydes preparation with similar results. In the second step—hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.
