29003-60-9Relevant articles and documents
Dichloroacetophenone Derivatives: A Class of Bioconjugation Reagents for Disulfide Bridging
Wu, Liu-Hai,Zhou, Shuguang,Luo, Qun-Feng,Tian, Jie-Sheng,Loh, Teck-Peng
supporting information, p. 8193 - 8197 (2020/11/18)
A mild and biocompatible method for the construction of disulfide bridging in peptides using dichloroacetophenone derivatives is developed. This method is highly selective (chemo, diastereo, regio, etc.) and atom economic and works under biocompatible reaction conditions (metal-free, water, pH 7, rt, etc.).
Method for preparing alpha,alpha-dihalogenated acetophenone compound
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Paragraph 0069-0074, (2020/02/04)
The invention belongs to the technical field of organic synthesis and in particular relates to a method for preparing an alpha,alpha-dihalogenated acetophenone compound. The preparation method provided by the invention comprises the following steps: in an alcohol solvent, enabling nitroalkenes, electrophilic halogen reagents and sodium hydride to react at 55-65 DEG C under a heating condition for5-10 hours, cooling the components to the room temperature, adding a diluted acid solution, and performing continue stirring for 2-5 hours, so as to obtain a target compound, namely alpha,alpha-dihalogenated acetophenone. The method for preparing the alpha,alpha-dihalogenated acetophenone compound, which is provided by the invention, is simple and efficient, mild in condition, easy in raw materialobtaining, green and environment-friendly and simple and convenient to operate, and as a synthesis intermediate, the obtained alpha,alpha-dihalogenated acetophenone compound has the potential of being widely used in fields such as medicine chemical engineering.
Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships
Zhang, Shao-Lin,Yang, Zheng,Hu, Xiaohui,Tam, Kin Yip
supporting information, p. 3441 - 3445 (2018/09/29)
Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.
One-pot dichlorinative deamidation of primary β-ketoamides
Zheng, Congke,Zhang, Xiaohui,Ijaz Hussain, Muhammad,Huang, Mingming,Liu, Qing,Xiong, Yan,Zhu, Xiangming
, p. 574 - 577 (2017/01/16)
An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.
Method for removal of methanamide by dichlorination
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Paragraph 0020-0049; 0065-0069, (2017/10/12)
A method for removal of methanamide by dichlorination is disclosed, according to the method, a finished product is obtained by removal of methanamide by dichlorination by one-step-reaction of various beta-carbonyl amide derivatives as raw materials, 2,2,6,6-Tetramethylpiperidinooxy (TEMPO) and an alkali as additives and N-chlorosuccinimide as a reagent in a reaction solvent, and then concentration and purification. According to the method, synthesis of an alpha-dichloroacetophenone derivative can be realized for the first time by a method of removal of methanamide by fracturation of carbon-carbon single bond. The method is novel and unique, has certain universality, is mild in reaction conditions, low in requirement of production equipment, and simple in technology, has the advantages of high efficiency, simple operation, high safety, economy and environmentally-friendliness; high-quality diverse alpha-dichloroacetophenone derivative products can be prepared by the method, and the products prepared by the method are important drug synthesis intermediates and material intermediates, can be widely used in the synthesis of heterocycles, unsaturated acids, acetylene alcohols and other compounds and cyclopropanation, and have wide market prospects.
A novel β-(oxy)alkyl radical during copper(I)-mediated stereoselective synthesis of (Z)-ene-1,4-diones in a reaction of 2,2,2-trichloro-1-phenylethanone
Ram, Ram N.,Tittal, Ram K.
supporting information, p. 2437 - 2440 (2016/05/19)
A novel β-(oxy)alkyl radical derived from trichloro methyl compound containing neither a suitably located C-C multiple bond nor a leaving group or a H-atom at the β-position of the radical in a reaction of 2,2,2-trichloro-1-phenyl-ethanone with 2 mol equiv each of CuCl and bpy in refluxing DCE under a N2 atm underwent intramolecular heterolysis (just like formation of intact radical cation-anion pair) during stereoselective radical dimerization to Z-ene-1,4-dione along with small amount of reductive dechlorination product. The stereochemistry was established by X-ray diffraction spectroscopy of various solid crystalline products.
Chemoselective Reduction of Trichloromethyl Compounds to gem-Dichloromethyl Groups Following Appel's Reaction Protocol
Romero-Reyes, Moises A.,Zaragoza-Galicia, Ivann,Olivo, Horacio F.,Romero-Ortega, Moises
, p. 9515 - 9519 (2016/10/14)
A simple and easy reduction of trichloroacetyl compounds following the modification of Appel's reaction protocol, using triphenylphosphine and methanol, afforded the corresponding dichloroacetyl compounds, with the exception of trichloroacetylmorpholine,
Vanadium-catalyzed chlorination under molecular oxygen
Moriuchi, Toshiyuki,Fukui, Yasuhiro,Kato, Satoshi,Kajikawa, Tomomi,Hirao, Toshikazu
, p. 177 - 180 (2015/03/04)
A catalytic chlorination of ketones was performed by using a vanadium catalyst in the presence of Bu4NI and AlCl3 under atmospheric molecular oxygen. This catalytic chlorination could be applied to the chlorination of alkenes to give the corresponding vic-dichlorides. AlCl3 was found to serve as both a Lewis acid and a chloride source to induce the facile chlorination. A combination of Bu4NI and AlI3 in the presence of a vanadium catalyst under atmospheric molecular oxygen induced the iodination of ketones.
A simple, mild, and efficient method for the preparation of α,α-dichloroketones with DCDMH catalyzed by ammonium chloride
Zheng, Zubiao,Han, Bingbing,Cheng, Peng,Niu, Jiangxiu,Wang, Aidong
, p. 9814 - 9818 (2015/01/09)
New process that can selectively prepare α,α-dichloro ketones from various ketones with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) using ammonium chloride as a catalyst is reported. The effects of ammonium salts, solvents, DCDMH, and reaction temperature were investigated. Under the optimal condition, most of α,α-dichlorinated products were selectively obtained in 86-98% yield.
Efficient partial hydrogenation of trichloromethyl to gem-dichloromethyl groups in platinum on carbon-catalyzed system
Sawama, Yoshinari,Imanishi, Takahiro,Nakatani, Ryosuke,Fujiwara, Yuta,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 4540 - 4546 (2014/06/10)
While gem-dichloromethyl groups can be directly synthesized by the mono-dechlorination of the corresponding trichloromethyl groups, the suppression control of the over-reduction to form chloromethyl or methyl functionalities is quite difficult. We have established the efficient and widely applicable mono-dechlorination method of the trichloromethyl groups to form the corresponding gem-dichloromethyl groups using platinum on carbon in dimethylacetamide as a specific solvent at 25 °C under a hydrogen atmosphere. The mono-dechlorination of the α,α,α- trichloromethylcarbonyl groups smoothly proceeded by the use of platinum on carbon as a catalyst in a highly chemoselective manner, while the efficient mono-dechlorination of the alkyl- and aryl-trichloromethyl groups required the combined use of Bu3SnH.
