- Preparation method of 4-(4-hydroxyphenyl) cyclohexanone
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The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 4-(4-hydroxyphenyl) cyclohexanone. According to the preparation method, p-bromophenol is used as a raw material, a Grignard reagent is prepared through hydroxyl protection and Grignard reaction, then the prepared Grignard reagent is utilized to couple with 1,4-cyclohexanedione monoethyleneglycol ketal, then the product is dehydrated to obtain alkene, and double protecting groups are removed after hydrogenation to prepare a target product, namely, 4-(4-hydroxyphenyl) cyclohexanone. Thepreparation method of 4-(4-hydroxyphenyl) cyclohexanone, provided by the invention, has the advantages of reasonable process design, high yield and low production cost; the prepared 4-(4-hydroxyphenyl) cyclohexanone is a white solid, the HPLC content is more than 99.5%, the total yield of the product can reach 75-80%, and the raw materials are easy to obtain; and the method has simple operation and high safety, and realizes industrial production of 4-(4-hydroxyphenyl) cyclohexanone.
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Paragraph 0068; 0076-0077
(2019/08/01)
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- Method for synthesizing 4-(4-hydroxyphenyl) cyclohexanone
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The invention belongs to the technical field of electronic material intermediate, and discloses a method for synthesizing 4-(4-hydroxyphenyl) cyclohexanone. The method comprises the following steps: reducing 4,4'-diphenol with Al-Ni to prepare 4-(4-cyclohexanamide)-phenol; then preparing 4-(4-benzyloxy-benzene) cyclohexanol with benzyl chloride protection; oxidizing with chromium trioxide to obtain 4-(4-benzyloxy-benzene) cyclohexanone; and finally hydrogenating with 5% Pd/C to obtain 4-(4-hydroxyphenyl) cyclohexanone having a molecular formula of C12H14O2. The 4-(4-hydroxyphenyl) cyclohexanone prepared by the method is an electronic material and medicinal intermediate; and the synthesizing method has the advantages of reasonable process design, high yield and short production cycle, is economical and feasible, and easily realizes industrial production.
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Paragraph 0034; 0035; 0036
(2017/07/20)
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- Method for synthesizing 4-(4'-hydroxy phenyl) cyclohexanone
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According to the background: 4-(4'-hydroxy phenyl) cyclohexanone is an important liquid crystal monomer, a medicine intermediate, a chemical raw material intermediate, a macromolecule intermediate, an antioxidant and the like. Along with rapid development of the crystal liquid and medicine industries in recent years, the demand on 4-(4'-hydroxy phenyl) cyclohexanone (I) is greatly increased; because of palladium-charcoal hydrogenation, a conventional process generally has defects of being large in environment pollution, poor in selectivity, low in yield, high in cost and the like. Aiming at the problems, the invention provides a novel process to solve the problems. Key points of the novel process are that firstly, an aluminum-nickel alloy is adopted to replace palladium of a heavy metal catalyst, so that pollution caused by heavy metals can be avoided; secondly, the cis/trans-selectivity can be up to 70%, the total yield can be up to 50%, the yield of a product is increased to a very large extent, and the production cost can be lowered.
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Paragraph 0001-0005
(2017/06/24)
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- Machines vs Malaria: A Flow-Based Preparation of the Drug Candidate OZ439
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An efficient preparation of the antimalarial drug candidate OZ439, which was obtained by integrating a machine-assisted approach with batch processes, is reported. This approach allows a rapid and cost-effective production of the key intermediates that we
- Lau, Shing-Hing,Galván, Alicia,Merchant, Rohan R.,Battilocchio, Claudio,Souto, José A.,Berry, Malcolm B.,Ley, Steven V.
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supporting information
p. 3218 - 3221
(2015/07/15)
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- Overcoming hERG activity in the discovery of a series of 4-azetidinyl-1-aryl-cyclohexanes as CCR2 antagonists
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A series of 4-azetidinyl-1-aryl-cyclohexanes as potent CCR2 antagonists with high selectivity over activity for the hERG potassium channel is discovered through divergent SARs of CCR2 and hERG.
- Zhang, Xuqing,Hufnagel, Heather,Markotan, Thomas,Lanter, James,Cai, Chaozhong,Hou, Cuifen,Singer, Monica,Opas, Evan,McKenney, Sandra,Crysler, Carl,Johnson, Dana,Sui, Zhihua
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p. 5577 - 5582
(2011/10/09)
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- 4-AZETIDINYL-1-PHENYL-CYCLOHEXANE ANTAGONISTS OF CCR2
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The present invention comprises compounds of Formula (I): wherein: X, R1, R2, R3, and R4 are as defined in the specification. The invention also comprises a method of preventing, treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is type II diabetes, obesity and asthma. The invention also comprises a method of inhibiting CCR2 activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula (I).
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Page/Page column 70
(2010/11/03)
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- Discovery of 1-amino-4-phenylcyclohexane-1-carboxylic acid and its influence on agonist selectivity between human melanocortin-4 and -1 receptors in linear pentapeptides
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Linear pentapeptides (Penta-cis-Apc-DPhe-Arg-Trp-Gly-NH2) containing 1-amino-4-phenylcyclohexane-1-carboxylic acid (cis-Apc) and substituted Apc are potent hMC4R agonists and they are inactive or weakly active in hMC1R, hMC3R, and hMC5R agonist assays. This study, together with our earlier report on 5-BrAtc, demonstrated the importance of replacing His 6 with phenyl-containing rigid templates in achieving good hMC4R agonist potency and selectivity against hMC1R in linear pentapeptides.
- Chu, Xin-Jie,Bartkovitz, David,Danho, Waleed,Swistok, Joseph,Cheung, Adrian Wai-Hing,Kurylko, Grazyna,Rowan, Karen,Yeon, Mitch,Franco, Lucia,Qi, Lida,Chen, Li,Yagaloff, Keith
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p. 4910 - 4914
(2007/10/03)
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- Process for producing alicyclic monoketones and process for producing alicyclic diketones
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The process for producing alicyclic monoketones (hydroxyphenylcyclohexanone derivatives) according to the present invention comprises hydrogenating substituted bisphenols such as bisphenol A in a solvent in the presence of a palladium/alkali metal catalyst in which palladium and an alkali metal are both supported on a carrier to obtain alicyclic monoketones such as 2-(4-oxocyclohexyl)-2-(4-hydroxyphenyl)propane. The process for producing alicyclic diketones according to the present invention comprises hydrogenating substituted bisphenols such as bisphenol A in a solvent in the presence of a palladium/alkali metal catalyst in which palladium and an alkali metal are both supported on a carrier to obtain alicyclic diketones such as 2,2-bis(4-oxocyclohexyl)propane and 4,4′-bicyclohexanone. The other process for producing alicyclic monoketones according to the present invention comprises hydrogenating biphenols such as bis(4-hydroxyphenyl) in an organic solvent in the presence of a palladium catalyst in which 10 to 30% by weight of palladium is supported on a carrier to obtain alicyclic monoketones such as 4(4′-hydroxyphenyl)cyclohexanone. According to the present invention, alicyclic monoketones or alicyclic diketones can be obtained with high selectivity and in high yields through simple steps, because the process includes only one reaction step to hydrogenate substituted bisphenols under relatively mild conditions.
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- Liquid crystalline compound, liquid crystal composition comprising the liquid crystal-line compound, and liquid crystal display device using the liquid crystal composition
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The invention is to provide liquid crystalline compounds which have a low viscosity, high negative dielectric anisotropy, high resistivity, and high voltage holding ratio, and are stable against heat and ultraviolet light; to provide liquid crystal compositions comprising the liquid crystalline compound; and to provide liquid crystal display devices using the liquid crystal composition therein; the liquid crystalline compound is expressed by the general formula (1) ?wherein R1and Y1represent an alkyl group having 1 to 20 carbon atoms; X1, X2, and X3independently represent single bond, 1,2-ethylene group, vinylene group, —COO—, —CF2O—, or —OCF2—; ring A1, ring A2, ring A3, and ring A4independently represent trans-1,4-cycloliexylene, or 1,4-phenylene hydrogen atom on the ring may be replaced by fluorine atom or chlorine atom provided that at least one of ring A2, ring A3, and ring A4represents 2,3-difluoro-1,4-phenylene; m and n are 0 or 1, and each element which constitutes this compound may be replaced by its isotope.
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- Alkenylcyclohexane liquid crystalline compounds
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Compounds of the formula STR1 wherein Z1 denotes a single covalent bond or --CH2 Ch2 --; ring A1 represents 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl or, when Z1 stands for --CH2 CH2 --, also trans-1,4-cyclohexylene; X1 stands for fluorine or chlorine; X2 signifies fluorine, chlorine or hydrogen, with the proviso that X2 only signifies hydrogen when X1 is chlorine or when ring A1 signifies pyridine-2,5-diyl and Z1 signifies --CH2 CH2 --; and R1 signifies 1E-alkenyl with 2 to 12 carbon atoms, their manufacture, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes.
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- Halobenzene liquid crystals
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Compounds of the formula STR1 wherein X1 denotes fluorine or chlorine and X2 denotes hydrogen, fluorine or chlorine; R1 is 3E-alkenyl, 4-alkenyl, 2E-alkenyloxy or 3-alkenyloxy; n stands for the number 0 or 1; one of the groups Y1 and Y2 is a single covalent bond, --COO--, --OOC--, --CH2 CH2 --, --CH2 O-- or --OCH2 -- and the other of the groups Y1 and Y2 is a single covalent bond; and rings A1 and A2 each individually are substituted or unsubstituted trans-1,4-cyclohexylene, in which optionally 2 non-adjacent CH2 groups are replaced by oxygen, or substituted or unsubstituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; with the proviso that X2 denotes fluorine or chlorine and/or Y1 or Y2 denotes --CH2 O-- or --OCH2 -- when simultaneously X1 is fluorine and R1 is 3E-alkenyl, and their use for liquid crystalline mixtures and electro-optical purposes.
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- Alkenylbicyclohexane liquid crystals
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Compounds of the formula STR1 wherein Z represents a single covalent bond or --CH2 CH2 --, R1 denotes 1E-alkenyl with 2-10 carbon atoms or 3E-alkenyl with 4-10 carbon atoms and R2 is alkyl with 1-10 carbon atoms, 2E-alkenyl with 3-10 carbon atoms or 3-alkenyl with 4-10 carbon atoms, as well as their use in liquid crystalline mixtures and for electro-optical purposes.
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