98790-22-8Relevant articles and documents
Stereoselective hydrogenation of lignin degradation model compounds
Hu,James,Rettig,Lee
, p. 1234 - 1239 (1997)
Di-μ-chloro-bis(η4-1,5-hexadiene)dirhodium(I) in a two-phase hexane-aqueous medium catalyzes the diastereoselective H2-hydrogenation of lignin degradation model compounds 4-propylphenol, 2-methoxy-4-propylphenol, and 2,6-dimethoxy-4-propylphenol. The all-cis diastereomer is obtained selectively when the phenolic hydroxy group is protected as a methyl ether or when a model compound possessing two methoxy substituents adjacent to the phenolic hydroxy group is used. The relative stereochemistries of the hydrogenated products are established by X-ray crystal structure analysis and (or) 1H NMR.
Hydrogenation of 4-propylphenol over carbon-supported palladium catalyst without external hydrogen: Effect of carbon support and palladium loading
Nagasawa, Yoshiyuki,Hiraishi, Yushi,Horyo, Daiki,Sobu, Tomoki,Taniguchi, Kenkichi,Nanao, Hidetaka,Sato, Osamu,Yamaguchi, Aritomo,Shirai, Masayuki
, p. 431 - 434 (2021/03/15)
The ring hydrogenation of 4-propylphenol in aqueous ethanol solution was studied over graphite- and activated carbon-supported palladium catalysts (Pd/G and Pd/C) with 0.15 wt % of palladium loadings without using external hydrogen. Decomposition of ethan
NUCLEUS HYDROGENATION METHOD FOR AROMATIC COMPOUND USING ALCOHOL AND WATER
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Paragraph 0018-0033, (2018/08/23)
PROBLEM TO BE SOLVED: To provide a method for the nucleus hydrogenation of an aromatic compound without using hydrogen for the improvement of safety and the diversification of a hydrogen source. SOLUTION: Provided is a method for the nucleus hydrogenation
The highly selective equatorial hydride delivery by biocatalysis: Chemoenzymatic synthesis of trans-2-(4-propylcyclohexyl)-1,3-propanediol via cis-4-propylcyclohexanol
Ikunaka, Masaya,Moriya, Narimasa,Nomoto, Fumiki,Ohsako, Akihiro,Okuda, Yoshiaki,Suenaga, Hitoshi
, p. 389 - 395 (2013/09/05)
4-Propylcyclohexanone 10a (69 g/L) is reduced by the catalysis of Galactomyces geotrichum JCM 6359 using i-PrOH (4.0 equiv) as an auxiliary substrate for recycling externally supplemented NAD+ (0.001 equiv) in 40 mM potassium phosphate buffer (pH 7.5) for 20 h to provide a mixture of cis-4-propylcyclohexanol 3a [cis/trans (99:0.5); 74%] and unconsumed 10a (22%). Practically pure 3a can be isolated in 69% yield after removing the entailed ketone 10a via bisulfite adduct formation. In the meantime, the crude reduction product [3a/10a (74:22)], without further purification, can be elaborated into trans-2-(4-propylcyclohexyl)-1,3-propanediol 1a, a compound deemed versatile in liquid-crystals development, in 30% overall yield from 10a in four steps.
Hydroamination of alkylphenols by nitriles
Tarasevich,Zhavrid,Kozlov
, p. 1154 - 1159 (2007/10/03)
N-(Alkyl(alkylcyclohexyl)amines were synthesized by hydroamination of o-, m-, and p-alkyl-phenols with aliphatic nitriles. The stereochemistry of the secondary amines formed is described.
ENZYMATIC "IN VITRO" REDUCTION OF KETONES. Part 10. Study of 3-Acetylpyridine Adenine Dinucleotide in a Co-enzyme Recycling System Ethanol-Ketone-3-AcPyAD+-HLAD
Lemiere, Guy L.,Jaco, Jan,Merckx, Erik M.,Lepoivre, Josef A.,Alderweireldt, Frank C.
, p. 747 - 752 (2007/10/02)
The NAD+ analogue 3-acetylpyridine adenine dinucleotide (3-AcPyAD+) has been studied in the co-enzyme recycling system ethanol-ketone-3-AcPyAD+-HLAD.All reaction parameters are tested in analogous conditions as for the NAD+-recycling system.The stereospecificity of the new system is investigated for the reduction of 4-, 3- and 2-alkylcyclohexanones.The new recycling system is kinetically and stereochemically very similar to the NAD+ system, but 3.2 times slower.
ENZYMATIC "IN VITRO" REDUCTION OF KETONES. VI.(1) Reduction rates and stereochemistry of the HLAD-catalyzed reduction of 3-alkyl- and 4-alkylcyclohexanones.
Osselaer, T. A. Van,Lemiere, G. L.,Lepoivre, J. A.,Alderweireldt, F. C.
, p. 133 - 150 (2007/10/02)
Reaction rate constants for the catalytic step HLAD-NADH + ketone * HLAD-NAD+ + alcohol in the HLAD-catalyzed reduction of 3-alkyl- and 4-alkylcyclohexanones are determined from initial rate measurements in the coenzyme recycling system ketone-ethanol-NAD+-HLAD.By rate measurements at several temperatures, activation parameters were determined and isokinetic relationships tracked down.Two different isokinetic relationships show that the 3-alkylcyclohexanones pass through an other type of transition state than cyclohexanone and the 4-alkylcyclohexanones, which means that they have a different arrangement on the HLAD-NADH complex.The results are rationalized in view of the most recent principles on nucleophilic additions to carbonyl functions.The resulting model for the HLAD-catalyzed reduction adequately explains the observed rate accelerating and decelerating effects and the stereochemistry of the reduction as well.
