trans-Phenyl-β-bromvinylketon | 34237-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-Phenyl-β-bromvinylketon
• 英文别名: (E)-3-bromo-1-phenylprop-2-en-1-one
• CAS: 34237-40-6
• 化学式: C₉H₇BrO
• 分子量: 211.058
• InChiKey: AOLSGJWZHCPMNX-VOTSOKGWSA-N

物化性质

• 熔点：
  29-30 °C
• 沸点：
  128-130 °C(Press: 6 Torr)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-Phenyl-β-bromvinylketon 在 过氧乙酸 作用下， 生成 cis-1-Benzoyl-2-phenylsulfonyl-ethylen
  参考文献：
  名称：

  Angeletti; Montanari, Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1958, vol. 16, p. 140

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯基-2-丙炔-1-酮 在 aluminum (III) chloride 、 sodium bromide 、 水 作用下， 以 乙腈 、 叔丁醇 为溶剂， 以69%的产率得到trans-Phenyl-β-bromvinylketon
  参考文献：
  名称：

  AlCl3–NaI(NaBr)–t-BuOH: mild, chemo- and stereoselective reagents for hydrohalogenation of propiolic derivatives

  摘要：

  (Z)-beta-lodo-propenamides and -beta-iodo-propenoic esters were selectively prepared in high yields, at room temperature, through reaction of 2-propynamides and 2-propynoic esters, respectively, with AlCl3 and Nal in the presence of t-BuOH in dichloromethane. These experimental conditions are compatible with the presence of acid sensitive acetal groups. Alternative use of EtOH or H2O in place of t-BuOH was investigated. (Z)-Bromo-propenamides and corresponding esters were prepared according to a similar procedure using sodium bromide in refluxing acetonitrile. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.08.032

文献信息

• Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective Conjugate Addition of Oxindoles to Electron-Deficient β-Haloalkenes
  作者：Qiaowen Jin、Changwu Zheng、Gang Zhao、Gang Zou

  DOI：10.1021/acs.joc.7b00571

  日期：2017.5.5

  A highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to β-haloalkene ketones/esters catalyzed by readily available chiral bifunctional quaternary ammonium salts is reported. This reaction provides efficient access to a range of 2-oxoindole derivatives bearing a thermodynamically unstable Z-olefin structure and a chiral quaternary carbon center in high yields (up to 90%) and

  据报道，由容易获得的手性双官能季铵盐催化的3-取代的羟吲哚向β-卤代烯烃酮/酯的高度Z-选择性不对称共轭加成反应。该反应可以高产率（高达90％）和良好至高的立体选择性（高达> 19：1 Z）有效地获得一系列带有热力学不稳定Z-烯烃结构和手性季碳中心的2-氧吲哚衍生物。/ E和91％ee）。
• Aroyl substituted dihydro-1,4-thiazines
  申请人：CIBA-GEIGY AG

  公开号：EP0166697A2

  公开（公告）日：1986-01-02

  Compounds of the formula I, wherein Ar is pyridyl, phenyl or phenyl substituted by halogen, halo-C1-4-alkyl, C1-4alkoxy or carboxy-C1-4-alkyl, n is zero, one or two, R' is hydrogen, C1-4alkyl, heterocyclyl-C2-4 alkyl, amino-C2-4alkyl, C1-4alkylamino-C2-4-alkyl, di-C1-4 alkylamino-C2-4alkyl or C1-4alkanoyl, and R2 is hydrogen, carboxy-C1-4alkyl or C1-4-alkoxy-carbonyl-C1-4-alkyl are disclosed as well as their preparation, pharmaceutical compositions containing the same and the use thereof as antirheumatic agents.

  公开了式 I 的化合物，其中 Ar 是吡啶基、苯基或被卤素、卤代-C1-4-烷基、C1-4-烷氧基或羧基-C1-4-烷基取代的苯基，n 是零、一个或两个，R'是氢、C1-4-烷基、杂环-C2-4-烷基、氨基-C2-4-烷基、C1-4-烷基氨基-C2-4-烷基、二-C1-4-烷基氨基-C2-4-烷基或 C1-4 烷酰基，R2 是氢、羧基-C1-4-烷基或 C1-4- 烷氧基-羰基-C1-4-烷基，还公开了它们的制备方法、含有它们的药物组合物以及它们作为抗风湿剂的用途。
• Kotschetkow; Winogradowa, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2745,2748; engl. Ausg. S. 2785, 2787
  作者：Kotschetkow、Winogradowa

  DOI：——

  日期：——
• A novel regio- and stereospecific hydrohalogenation reaction of 2-propynoic acid and its derivatives
  作者：Shengming Ma、Xiyan Lu、Zhigang Li

  DOI：10.1021/jo00028a055

  日期：1992.1

  2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products. A rationale for the regio- and stereospecificity is briefly discussed.
• Angeletti; Montanari, Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1958, vol. 16, p. 140
  作者：Angeletti、Montanari

  DOI：——

  日期：——