10596-48-2Relevant academic research and scientific papers
β-Carbonyl substituted glutathione conjugates as inhibitors of O. volvulus GST2
Brophy, Peter M.,Campbell, Alison M.,Van Eldik, Annamaria J.,Teesdale-Spittle, Paul H.,Liebau, Eva,Wang, Meng F.
, p. 979 - 981 (2000)
A series of β-carbonyl substituted glutathione conjugates were prepared and evaluated as inhibitors of OvGST2. Their specificity for the parasite derived protein was assessed through comparison with their inhibition of human πGST. Inhibition of OvGST2 has been demonstrated at low micromolar concentrations for these conjugates and selectivity for OvGST2 over human π-GST of greater than 10-fold has been achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.
PALLADIUM CATALYZED OXIDATION OF Δ2, Δ3, AND Δ4-UNSATURATED ALCOHOLS
Tamaru, Yoshinao,Inoue, Kenji,Yamada, Yoshimi,Yoshida, Zen-ichi
, p. 1801 - 1802 (1981)
Palladium (0.63 molpercent) catalyzes the oxidation of Δ2, Δ3, and Δ4-unsaturated alcohols to the corresponding ketones in good yields, where bromomesitylene or bromobenzene is used as an oxidant.
Decarboxylative Nazarov Cyclization-Based Chirality Transfer for Asymmetric Synthesis of 2-Cyclopentenones
Komatsuki, Keiichi,Kozuma, Akane,Saito, Kodai,Yamada, Tohru
, p. 6628 - 6632 (2019)
Asymmetric synthesis of 2-cyclopentenones was achieved by chirality transfer based on Lewis acid catalyzed decarboxylative Nazarov cyclization of optically active cyclic enol carbonates, which are prepared by silver-catalyzed carbon dioxide incorporation into optically pure propargyl alcohols. The stereochemistry at the 4,5-positions of the 2-cyclopentenones was cleanly constructed by reflecting the stereochemistry of the starting materials. This method could be applied to various substrates to obtain the corresponding products in high yields with highly efficient chirality transfer.
Evaluation of some thiosemicarbazones of arylidene ketones and analogues for anticonvulsant activities
Dimmock, J. R.,Jonnalagadda, S. S.,Hussein, S.,Tewari, S.,Quail, J. W.,et al.
, p. 581 - 588 (1990)
A number of thiosemicarbazones of arylidene and aryl ketones were prepared as candidate anticonvulsant agents.X-Ray crystallography of 4-(4-methylphenyl)-3-buten-2-one thiosemicarbazone (1a) revealed that it had the E configuration with respect to both olefinic and carbimino double bonds.Other structural features of this anticonvulsant compound were noted.Most of the compounds displayed activity in the MES and/or scMET tests and of particular interest was acetophenone thiosemicarbazone (4b) which had good activity when administered by the intraperitoneal and oral routes.High resolution 1H NMR spectroscopy of selected compounds in dimethylsulphoxide-d6 revealed that in most cases equilibrium was attained of mixtures of E and Z isomers pertaining to the stereochemistry of the carbimino group.In general this isomeric ratio was dependent on the size of the R group attached to the carbimino function.
Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols
Kwon, Min Serk,Kim, Namdu,Seo, Seong Hyeok,Park, In Soo,Cheedrala, Ravi Kumar,Park, Jaiwook
, p. 6913 - 6915 (2005)
(Chemical Equation Presented) An air-stable, heterogeneous, and recyclable catalyst composed of palladium nanoparticles entrapped in aluminum hydroxide was applied to a highly selective α alkylation. A wide range of aliphatic and aromatic ketones and primary alcohols were coupled to prepare enones in an O2 atmosphere and ketones in an argon atmosphere (see scheme).
Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide
Matsumoto, Shoji,Marumoto, Hayato,Akazome, Motohiro,Otani, Yasuhiko,Kaiho, Tatsuo
, p. 590 - 599 (2021/03/29)
The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.
Asymmetric transfer hydrogenation of cycloalkyl vinyl ketones to allylic alcohols catalyzed by ruthenium amido complexes
Liu, Sensheng,Cui, Peng,Wang, Juan,Zhou, Haifeng,Liu, Qixing,Lv, Jinliang
supporting information, p. 264 - 267 (2019/01/10)
A chemoselective 1,2-reduction of cycloalkyl vinyl ketones via asymmetric transfer hydrogenation is described. The reduction proceeded smoothly with a chiral diamine ruthenium complex as a catalyst and a HCOOH-NEt3 azeotrope as both a hydrogen source and solvent under mild conditions. A wide range of 1-cycloalkyl chiral allylic alcohols were obtained in good yields and up to 87% ee. It was found that the alkyl group plays an important role in the enantioselectivity.
Iridium-catalysed desilylative acylation of 1-alkenylsilanes
Zaranek, Maciej,Skrodzki, Maciej,Szudkowska-Fr?tczak, Justyna,Dodot, Maciej,Kownacki, Ireneusz,Orwat, Bartosz,Pawlu?, Piotr
, p. 75 - 78 (2016/12/07)
We report the iridium-catalysed desilylative acylation of styryl and dienyl silanes by acid anhydrides to afford (E)-α,β-unsaturated ketones. The [{Ir(μ-Cl)(cod)}2] catalyst is the first non-rhodium complex successfully applied for this type of
Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones
Komatsuki, Keiichi,Sadamitsu, Yuta,Sekine, Kohei,Saito, Kodai,Yamada, Tohru
supporting information, p. 11594 - 11598 (2017/09/11)
Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.
Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights
Ueda, Atsushi,Umeno, Tomohiro,Doi, Mitsunobu,Akagawa, Kengo,Kudo, Kazuaki,Tanaka, Masakazu
, p. 6343 - 6356 (2016/08/16)
Helical peptide foldamer catalyzed Michael addition reactions of nitroalkane or dialkyl malonate to α,β-unsaturated ketones are reported along with the mechanistic considerations of the enantio-induction. A wide variety of α,β-unsaturated ketones, including β-aryl, β-alkyl enones, and cyclic enones, were found to be catalyzed by the helical peptide to give Michael adducts with high enantioselectivities (up to 99%). On the basis of X-ray crystallographic analysis and depsipeptide study, the amide protons, N(2)-H and N(3)-H, at the N terminus in the α-helical peptide catalyst were crucial for activating Michael donors, while the N-terminal primary amine activated Michael acceptors through the formation of iminium ion intermediates.
