770-85-4Relevant academic research and scientific papers
Rearrangement of Ketones. Part 3. Kinetic Study and Intermediate Complexes in the Reaction of t-Butyl Phenyl Ketone with Aluminium Chloride
Fernandez-Monreal, Maria C.,Ruiz, Maria P.,San-Roman, Julio
, p. 1983 - 1988 (1988)
A kinetic study of the rearrangement of t-butyl phenol ketone to 3-methyl-3-phenylbutan-2-one with aluminium chloride is reported.In addition, a study by (1)H and (13)C n.m.r. of the system t-butyl phenyl ketone-aluminium chloride in benzene shows the con
Synthetic method of methyl ketone compound
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Paragraph 0047-0054, (2020/06/16)
The invention relates to the technical field of organic synthesis, and provides a synthesis method for a methyl ketone compound. The synthesis method comprises the following steps: mixing terminal alkyne, an organic solvent, an acid and water, and carrying out a hydration reaction to obtain a methyl ketone compound. According to the synthetic method provided by the invention, the use a catalyst containing metal ions and an oxidizing agent can be avoided, the raw materials are directly subjected to the hydration reaction in the presence of acid and water, and the complicated operation of removing metal ions is avoided in the post-treatment process of the produced methyl ketone compound; the method provided by the invention is high in raw material conversion rate and relatively high in product yield and product purity; the synthesis reaction process is simple and convenient to operate, green and environment-friendly, and suitable for large-scale industrial production; the synthetic method provided by the invention is mild in reaction conditions and easy to control. Results of an embodiment of the invention show that when the method is used for preparing the methyl ketone compound, yield can reach 96.4%, and product purity reaches 99.2%.
Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline
Shi, Hui,Du, Chuan,Zhang, Xinhang,Xie, Fukai,Wang, Xiaoyu,Cui, Shanshan,Peng, Xiaoshi,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
, p. 1312 - 1319 (2018/02/09)
A microwave-irradiated solvent-free pinacol rearrangement of hydrobenzoin substrates catalyzed by a combination of N-fluorobenzenesulfonimide and FeCl3·6H2O was developed. Its selectivity was first investigated by density functional theory (DFT) calculations. Then the functional group tolerance was examined by synthesizing a series of substrates designed based on the insight provided by the DFT calculations. The application of the methodology was demonstrated by the efficient one-pot synthesis of (±)-latifine and (±)-cherylline, both are 4-aryltetrahydroisoquinoline alkaloids isolated from Amaryllidacecae plants.
A gold catalytic pinacone method of rearrangement of
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Paragraph 0067; 0068; 0069; 0070; 0071, (2017/11/22)
The invention provides a method used for catalytic rearrangement of pinacol with gold. A reaction general formula is disclosed in the invention, wherein R1, R2, R3, and R4 may be common alkyl, cycloalkyl, and aromatic rings. A gold catalyst needed by reac
Rhenium complex-catalyzed Meinwald rearrangement reactions of oxiranes
Umeda, Rui,Muraki, Masahito,Nakamura, Yuudai,Tanaka, Tomoyuki,Kamiguchi, Kyohei,Nishiyama, Yutaka
supporting information, p. 2393 - 2395 (2017/05/29)
The Meinwald rearrangement reaction of oxiranes to the corresponding carbonyl compounds is efficiently catalyzed by the ReBr(CO)5 complex.
6,11-dihydro-5H-benzo[d]imidazo[1,2-a]azepines derivatives as histamine H4 receptor ligands
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, (2016/03/06)
The present patent application concerns new ligands of the H4-receptor, their process of preparation and their therapeutic use.
AuCl3/AgSbF6-catalyzed rapid epoxide to carbonyl rearrangement
Gudla, Vanajakshi,Balamurugan, Rengarajan
, p. 5243 - 5247 (2012/11/07)
An efficient epoxide to carbonyl rearrangement using catalytic AuCl 3/AgSbF6 has been presented. The reactions are fast and high yielding. β-Hydrogen migration takes place exclusively when hydrogen and methyl or substituted methyl groups are present at β-carbon of epoxide. When phenyl/acetyl/benzoyl and hydrogen are available at same carbon atom, migration of the former is preferred over the latter.
Enantioselective borohydride reduction of aliphatic ketones catalyzed by ketoiminatocobalt(iii) complex with 1-chlorovinyl axial ligand
Tsubo, Tatsuyuki,Chen, Hsiu-Hui,Yokomori, Minako,Fukui, Kosuke,Kikuchi, Satoshi,Yamada, Tohru
supporting information; scheme or table, p. 780 - 782 (2012/09/22)
For the enantioselective borohydride reduction of aliphatic ketones, the optically active ketoiminatocobalt(II) catalysts was successfully designed based on their axial ligand. Instead of chloroform for the aryl ketone reduction, various axial ligand precursors were examined for the aliphatic ketone. Consequently, 1, 1, 1-trichloroethane was found to be the most effective activator of the cobalt(II) complexes to generate the corresponding 1-chlorovinyl cobalt(III) derivatives as the reactive intermediate. Several aliphatic ketones were successfully reduced to afford the corresponding secondary alcohols with high enantioselectivities.
Cyanocuprates convert carboxylic acids directly into ketones
Genna, Douglas T.,Posner, Gary H.
supporting information; experimental part, p. 5358 - 5361 (2011/12/15)
Carboxylic acids were converted directly in 56-99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R2CuLi 3 LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate.
β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Tyte, Melloney J.
supporting information; experimental part, p. 2936 - 2939 (2010/09/10)
A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.
