77866-58-1Relevant academic research and scientific papers
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
Process for the preparation of liquid crystalline ethers
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Page/Page column 9-11, (2010/02/11)
Preparation of 4- or 4'-mono- and 4,4'-di-substituted (bi)cyclohexyl (bi)cyclohexylmethyl ethers (I) by reducing corresponding (bi)cyclohexyl (cyclohexyl)cyclohexanoates (II) comprises reacting 1 molar equivalent (II) with 2-6 molar equivalent of an optionally mono-, di- or tri-substituted silane (III) in a free radical chain reaction, optionally in a solvent. Preparation of 4- or 4'-mono- and 4,4'-di-substituted (bi)cyclohexyl (bi)cyclohexylmethyl ethers (I) by reducing corresponding (bi)cyclohexyl (cyclohexyl)cyclohexanoates (II) comprises reacting 1 molar equivalent (II) with 2-6 molar equivalent of an optionally mono-, di- or tri-substituted silane R1>1>R1>2>R1>3>SiH (III) of the following formulae in a free radical chain reaction, optionally in a solvent: [Image] [Image] R1>, R2>1-12C alkyl or 2-12C alkenyl, which is an unsubstituted or has one CN or CF3 substituent or at least one halogen substituent and may have CH2 group(s) replaced by -O-, -S-, cyclopropan-1,2-diyl or cyclobutan-1,3-diyl, without directly linked O atoms, or H in one case only; R3>-R6>H, halogen, methyl or CN; R11>-R13>Cl in at least one case, otherwise H, 1-8C alkyl, 1-8C alkoxy, cyclohexyl, methylcyclohexyl, cyclopentyl or phenyl or R1>1>R1>2> is a -(CH2)r- group; m, n : 0 or 1; r : 4 or 5 An independent claim is included for the preparation of symmetric di-(bi)cyclohexyl(alkyl) ethers (XXI) with 1-3 C alkyl groups: [Image] p, q : 0, 1, 2 or 3; p+q : 1, 2 or 3.
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.
Stereoselective hydrogenation of lignin degradation model compounds
Hu,James,Rettig,Lee
, p. 1234 - 1239 (2007/10/03)
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.
The Thermal Properties of (4-Substituted Cyclohexyl) 4-Substituted Cinnamates
Hayashi, Shigetsugu,Takenaka, Shunsuke,Kusabayashi, Shigekazu
, p. 283 - 284 (2007/10/02)
The thermal properties for a homologous series of 4-alkylcyclohexyl 4-alkoxy- and 4-cyanocinnamates are examined.They exhibit nematic phases with low melting points.The effect of the cyclohexyl group on the mesophase stability is discussed.
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.
