Allyl (Z)-3-bromopropenoate | 132973-28-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Allyl (Z)-3-bromopropenoate
• 英文别名: (Z)-3-bromoacrylic acid allyl ester；prop-2-enyl (Z)-3-bromoprop-2-enoate
• CAS: 132973-28-5
• 化学式: C₆H₇BrO₂
• 分子量: 191.024
• InChiKey: XHLSZYNPESJPRK-ARJAWSKDSA-N

物化性质

• 沸点：
  195.6±23.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  allyl propiolate 在 aluminum (III) chloride 、 sodium bromide 、 水 作用下， 以 乙腈 、 叔丁醇 为溶剂， 以57%的产率得到Allyl (Z)-3-bromopropenoate
  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

• 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.
• Differentiation of the reactivities of carbon-carbon multiple bonds in one molecule. Highly chemo- and stereo-selective hydrohalogenation of allyl or propargyl propiolates
  作者：Shengming Ma、Xiyan Lu

  DOI：10.1016/s0040-4039(00)97323-4

  日期：1990.1

  The reaction of allyl or propargyl propiolates with lithium halides in acetic acid afforded allyl or propargyl (Z)-3-halopropenoates highly chemo- and stereo-selectively by differentiation of reactivities of carbon-carbon multiple bonds in the same molecule.
• MA, SHENGMING;LU, XIYAN, TETRAHEDRON LETT., 31,(1990) N2, C. 7653-7656
  作者：MA, SHENGMING、LU, XIYAN

  DOI：——

  日期：——