6641-83-4Relevant academic research and scientific papers
Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts
Alsters, Paul L.,Chou, Khi Chhay,De Wildeman, Stefaan M. A.,Faber, Teresa,Hadavi, Darya,Han, Peiliang,Quaedflieg, Peter J. L. M.,Schwalb Freire, Alfonso J.,Verzijl, Gerard K. M.,van Slagmaat, Christian A. M. R.
supporting information, p. 10102 - 10112 (2021/08/03)
The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.
Preparation γ - carbonyl carboxylic acid, amino acid, amino acid ester and amide compounds
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Paragraph 0039; 0040; 0041; 0042; 0044, (2017/06/21)
The invention discloses a method for preparing gamma-carbonyl carboxylic acid, amino acid, amino acid ester and amide compounds. The method comprises the following steps: uniformly mixing a methylene-containing compound, an oxidizing agent and water to perform selective methylene carbon-hydrogen bond oxidation, so as to obtain at least one of gamma-carbonyl carboxylic acid, gamma-carbonyl amino acid and gamma-carbonyl amide compounds after the reaction is finished. The method is a methylene selective oxidation reaction which does not need a catalyst for catalysis and employs a persulfate as an oxidizing agent, and the reaction is successfully applied to oxidation of methylene carbon-hydrogen bonds of carboxylic acids, amino acids and amide compounds, excellent selectivity is obtained, and the method has important application value.
Formation of γ-oxoacids and 1 H-pyrrol-2(5 H)-ones from α,β-unsaturated ketones and ethyl nitroacetate
Aginagalde, Maialen,Bello, Tamara,Masdeu, Carme,Vara, Yosu,Arrieta, Ana,Cossio, Fernando P.
experimental part, p. 7435 - 7438 (2010/12/25)
Michael addition of ethyl nitroacetate on α,β-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus prepared into 1H-pyrrol-2(5H)-ones by reaction with primary amines under Paal-Knorr conditions is also reported.
Electrocarboxylation de composes carbonyles aliphatiques, aromatiques et vinyliques: interet de l'utilisation d'une anode consommable en magnesium
Mcharek, Slah,Heintz, Monique,Troupel, Michel,Perichon, Jacques
, p. 95 - 97 (2007/10/02)
In the presence of carbon dioxide in DMF, the electroreduction of carbonyl compounds or α,β-ketoalkenes at high concentration yields respectively α-hydroxyacids and β-ketoacids.The use of a sacrificial magnesium anode allows constant current electrolyses in a diaphragmless cell.
Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids
Yates, Peter,Burke, Patrick Michael
, p. 1695 - 1704 (2007/10/02)
Reaction of tetrahydro-2,2,5,5-tetramethyl-3(2H)-furanone (1) with 96 or ca. 100percent sulfuric acid or hot polyphosphoric acid followed by aqueous quenching gave the following products: 2-hydroxy-2,5-dimethyl-4-hexen-3-one (3), 2,4,4-trimethyl-2-cyclopenten-1-one (7), 3,5,5-trimethyl-2-cyclopenten-1-one (8), tetrahydro-2,3,5,5-tetramethylfuran-2,3-diol (11), 2,5-dihydro-3,5,5-trimethyl-2-methylenefuran (17) and its dimer 20, 2,5-dihydro-2,3,5,5-tetramethyl-2-furanol (18), 4-hydroxy-2,4-dimethyl-2-pentenoic acid γ-lactone (22), 2,3,5-trimethyl-2-cyclopenten-1-one (23), and tetramethylfuran (25).In 96percent sulfuric acid the products arise by ring opening, ring opening followed by reclosure to carbocyclic products, methyl migration from C-2 to C-3 to give rearranged furan derivatives, and oxidation.In ca. 100percent sulfuric acid or hot polyphosphoric acid further methyl migrations can occur to give 23 and 25.
Reactions radicalaires du percarbonate de O,O-tert-butyle et O-isopropenyle: acetonylations assistees par un co-amorceur
Jaouhari, Rabih,Filliatre, Claude,Villenave, Jean-Jacques
, p. 2295 - 2298 (2007/10/02)
By decomposition in alkanes, ethers, ketones, acids, esters and nitriles of equimolecular mixtures of O,O-tert-butyl and O-isopropenyl peroxicarbonate and tert-butyl peroxyacetate, the "assisted" acetonylation of the solvents has been accomplished.The presence of the co-initiator allows the yield of the free radical acetonylation to be markedly improved: the formation of the by-product acetonylacetone is avoided and the yield of acetonylated derivatives is strongly enhanced while the regioselectivity of the processes is preserved and even increased in some cases.
Optical resolution of acylthiopropionic acid
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, (2008/06/13)
A process for the optical resolution of DL-α-methyl-β-acylthiopropionic acid, which comprises contacting a DL-α-methyl-β-acylthiopropionic acid of the formula, STR1 wherein R1 is acetyl or benzoyl which may be substituted with a C1 -C3 alkyl or a halogen atom, with an optically active amine of the formula, STR2 wherein R2 is methyl, isopropyl or isobutyl, to form diastereoisomeric salts, subjecting the formed diastereoisomeric salts to the fractional crystallization in a solvent to separate the D-acid salt from the L-acid salt, and then contacting the individual diastereoisomeric salt with acid to give D-α-methyl-β-acylthiopropionic acid and L-α-methyl-β-acylthiopropionic acid, the former being useful as an intermediate for synthesizing captopril useful as an antihypertensive agent.
