- Green synthesis method of medical intermediate benzocyclohexanone compound
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The invention provides a green synthesis method of a benzocyclohexanone compound, and belongs to the technical field of organic synthesis. The method provided by the invention comprises the followingsteps: by taking 4-phenylbutyric acid as a raw material, firstly carrying out reflux reaction with oxalyl chloride in dichloromethane, carrying out vacuum evaporation to dryness to obtain a crude product of the 4-phenylbutyryl chloride compound, then dissolving the crude product in a solvent, adding a metal-doped modified molecular sieve catalyst to start reaction, and stirring the solution at different temperatures to carry out ring closing reaction, thereby obtaining the product; and after the reaction is finished, carrying out suction filtration, solvent washing, column chromatography purification and other operations to obtain the target product benzocyclohexanone compound. The synthesis method disclosed by the invention is environment-friendly in reaction and simple and convenient tooperate, the catalyst can be recycled, and the synthesis method is suitable for green synthesis of the benzocyclohexanone compound.
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Paragraph 0032-0034
(2020/12/30)
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- An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β-Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane
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An efficient and general trifluoromethylthiolation of silylenol ethers and β-naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α-trifluoromethylthiolated carbonyl compounds and β-naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α-trifluoromethylthiolated (+)-4-cholesten-3-one and naphthoquinone. (Figure presented.).
- Saravanan, Perumal,Anbarasan, Pazhamalai
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p. 2894 - 2899
(2018/08/17)
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- A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion
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A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.
- Yu, Jiajia,Zhao, Huijun,Liang, Shuguang,Bao, Xiaoguang,Zhu, Chen
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supporting information
p. 7924 - 7927
(2015/07/27)
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- Sustainable flow oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst
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A flow chemistry process for the Oppenauer oxidation of benzylic secondary alcohols using partially hydrated zirconium oxide and a simple carbonyl containing oxidant such as acetone, cyclohexanone, and neopentanal is reported. The heterogeneous oxidative system could be applied to a wide range of functionalized alcohol substrates, allowing clean and fast delivery of ketone products within a few minutes between 40 and 100 C.
- Chorghade, Rajeev,Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
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supporting information
p. 5698 - 5701
(2013/12/04)
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- Synthesis of Substituted Chrysenes
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Syntheses of 3-ethyl-9-methylchrysene (9) and 1,3,9-trimethylchrysene (9a) are described. 2-(7'-Ethyl-1'-naphthyl)ethyl bromide (6) and 2-(5',7'-dimethyl-1'-naphthyl)ethyl bromide (6a) were condensed separately with 2-carbethoxy-5-methylcyclohexanone to afford ethyl α,α-(4-methyl-2-cyclohexanone)-γ-(7'-ethyl-1'-naphthyl)butyrate (7) and ethyl α,α-(4-methyl-2-cyclohexanone)-γ-(5',7'-dimethyl-1'-naphthyl)butyrate (7a) respectively.PPA cyclisation of 7 gave a mixture of 8 and 8b while that of 7a gave only 8a.Catalytic dehydrogenation of 8 and 8b afforded 9 and that of 8a gave 9a.The products were characterised by physical data.
- Mitra, Ashutosh,Ghosh, Swati
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- The Photochemistry of 2,2-Dimethyl- and 2-Aryl-2-methylnaphthalen-1(2H)-ones. Substitution Requirement for the Oxadi-?-methane Rearrangement
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The photochemistry of 2-aryl-2-methylnaphthalen-1(2H)-ones (1) and (2), 2,2-dimethylnaphthalen-1(2H)-one (6), 2,2,3-trimethylnaphthalen-1(2H)-one (7), 2,2,4-trimethylnaphthalen-1(2H)-one (3), 2-(p-methoxyphenyl)-2,4-dimethylnaphthalen-1(2H)-one, (8), and 2,2,5,7-tetramethylnaphthalen-1(2H)-one (12) has been examined.The compounds which did not contain a 4-substituent, (1), (2), (6), and (7), were virtually unchanged under conditions which caused the 4-methyl derivative (3) to undergo an oxadi-?-methane (ODPM) rearrangement to the 1,1a-dihydrocyclopropindenone (4).Similar reactivity was shown by the 4-methyl derivative (8), which gave the ODPM rearrangement products (9) and (10).On further irradiation, both (9) and (10) underwent rearrangement to 4-(p-methoxyphenyl)-3,4-dimethylnaphthalen-1(4H)-one (11).The 4-methyl group in (3) and (8) would appear to be exerting a steric effect, since irradiation of 2,2,5,7-tetramethylnaphthalen-1(2H)-one (12) produced the 1-naphthol (13) and the 1-tetralone (14), both of which arise from further reaction of an ODPM rearrangement product.Syntheses of the naphthalen-1(2H)-ones (1), (8), and (12) are reported.
- Greenland, Harry,Kozyrod, Robert P.,Pinhey, John T.
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p. 2011 - 2016
(2007/10/02)
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- Novel Synthesis of 5,5-Dimethyl-1-octalin Derivatives
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Pyrolysis of 3-isopropenyl-2-allylcyclohex-2-en-1-one (4) at ca. 275 deg C yielded 3,4,5,6-tetrahydro-5,5-dimethyl-1(2H)-naphthalenone (1) as the chief product.Higher pyrolysis temperatures also yielded methyl substituted α-tetralones derived from 1.Reductive methylation of 1 gave the trans-angularly methylated derivative 9 as the only product.The dienolate intermediate in this transforamtion was also trapped as a trimethyl ether, 8.Mechanisms for the pyrolytic rearrangement and the reductive alkylation are discussed.
- Munslow, William D.,Reusch, William
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p. 5096 - 5099
(2007/10/02)
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