1655-00-1Relevant academic research and scientific papers
Production process of cyclohexanecarboxylic acid
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Paragraph 0018; 0023; 0024, (2018/09/08)
The invention discloses a production process of cyclohexanecarboxylic acid and belongs to the field of chemical synthesis. Cyclohexene oxide is used herein as a starting material to react with carbondioxide, Mg powder and TMSCl (trimethylsilyl chloride); Pd/C catalytic hydrogenation is performed in the presence of an acid to obtain the cyclohexanecarboxylic acid. The production process has good safety and good operational simplicity and is suitable for industrial production.
Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles
Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca
supporting information, p. 3366 - 3369 (2016/07/26)
A stereoselective bioreduction of 2-oxocycloalkanecarbonitriles was concurrently coupled to a whole cell-catalyzed nitrile hydrolysis in one-pot. The first step, mediated by ketoreductases, involved a dynamic reductive kinetic resolution, which led to 2-hydroxycycloalkanenitriles in very high enantio- and diastereomeric ratios. Then, the simultaneous exposure to nitrile hydratase and amidase from whole cells of Rhodococcus rhodochrous provided the corresponding 2-hydroxycycloalkanecarboxylic acids with excellent overall yield and optical purity for the all-enzymatic cascade.
Stereochemistry of the Inhibition of δ-Chymotrypsin with Optically Active cis-Decaline-Type Organophosphates: 31P-NMR Studies
Furegati, Stefan,Ganci, Walter,Przibille, Georg,Rüedi, Peter
, p. 1127 - 1138 (2007/10/03)
Investigation of the inhibition of δ-chymotrypsin with the four novel, optically active, axially and equatorially substituted cis-3-(2,4-dinitrophenoxy)-2,4-dioxa-3λ 5-phosphabicyclo[4.4.0]decan-3-ones (= 3-(2,4-dinitrophenoxy)hexahydro-4H-1,3,
Chemoselective Enzymatic Hydrolysis of Aliphatic and Alicyclic Nitriles
Raadt, Anna de,Klempier, Norbert,Faber, Kurt,Griengl, Herfried
, p. 137 - 140 (2007/10/02)
Mild and selective hydrolysis of aliphatic and alicycic nitriles leading to carboxylic acids and amides was achieved under neutral conditions by an immobilized enzyme preparation from Rhodococcus sp.This method is particularly useful for the transformation of compounds containing other acid- or basesensitive groups.
Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase
Klempier,De Raadt,Faber,Grieng
, p. 341 - 344 (2007/10/02)
Using an immobilized nitrilase from Rhodococcus sp. mild and selective hydrolysis of nitriles can be achieved even in the presence of acid or base sensitive groups under neutral conditions. This method is applicable to a broad range of substrates as exemplified by aliphatic, alicyclic, heterocyclic and carbohydrate type nitriles.
Mono- and Dialkylation of Derivatives of (1R,2S)-2-Hydroxycyclopentanecarboxylic Acid and -cyclohexanecarboxylic Acid via Bicyclic Dioxanones: Selective Generation of Three Contiguous Stereogenic Centers on a Cyclohexane Ring
Herradon, Bernardo,Seebach, Dieter
, p. 690 - 714 (2007/10/02)
Ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate and -cyclohexanecarboxylate (1a and 2a, respectively) obtained in 40 and 70 percent yield by reduction of 3-oxocyclopentanecarboxylate and cyclohexanecarboxylate, respectively (Scheme 2), with non-fermenting
DIASTEREOSELECTIVE ELABORATION OF THE CARBON SKELETON OF β-HYDROXYESTERS FROM YEAST REDUCTIONS PREPARATION OF (2S)-2-HYDROXY-CYCLOHEXANE CARBOXYLIC ACIDS WITH THREE CONTIGUOUS STEREOGENIC CENTERS
Seebach, Dieter,Herradon, Bernardo
, p. 3791 - 3794 (2007/10/02)
The dioxanone-type acetal 2 from (1R,2S)-2-hydroxy-cyclo-hexane carboxylic acid (1) and pivalaldehyde is dehydrogenated to a derivative 3 of 6-hydroxy-cyclohexene carboxylic acid.Highly selective Michael additions and trapping of the resulting enolates wi
Reduction of Substituted Δ2-Isoxazolines. Synthesis of β-Hydroxy Acid Derivatives
Curran, Dennis P.,Scanga, Susan A.,Fenk, Christopher J.
, p. 3474 - 3478 (2007/10/02)
Three separate methods are reported for the formation of β-hydroxy acid derivatives from readily available substituted Δ2-isoxazolines.Cycloaddition of 2,2-dimethylpropanenitrile oxide with a variety of olefins followed by reductive cleavage produces α '-tert-butyl β-hydroxy ketones.These are cleaved to β-hydroxy tert-butyl esters by Baeyer-Villiger oxidation with peroxytrifluoroacetic acid.In the second approach, α ',β-dihydroxy ketones are generated via cycloaddition of olefins with the nitrile oxide generated from 2--2-methyl-1-nitropropane followed by reductive ring opening.Standard periodic acid cleavage gives β-hydroxy acids.Finally, 3-methoxy-substituted Δ2-isoxazolines, readily available via benzenesulfonylcarbonitrile oxide-olefin cycloaddition and methoxide displacement, are directly reduced to β-hydroxy esters.
144. Ueber die Stereoselektivitaet der α-Alkylierung von (1R,2S)(+)-cis-2-Hydroxy-cyclohexancarbonsaeureaethylester
Frater, Gyoergy
, p. 1383 - 1390 (2007/10/02)
In continuation of our work on the stereoselectivity of the α-alkylation of β-hydroxyesters , we studied this reaction with the title compound (+)-2.The latter was prepared through reduction of 1 with baker's yeast.Alkylation of the dianion of (+)-
