2-acetoxy-1-phenylethylamine hydrobromide | 133649-07-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-acetoxy-1-phenylethylamine hydrobromide
• CAS: 133649-07-7
• 化学式: BrH*C₁₀H₁₃NO₂
• 分子量: 260.131
• InChiKey: CLPICGPHGCONHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-acetoxy-1-phenylethylamine hydrobromide 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-(N-acetylamino)-2-phenylethanol
  参考文献：
  名称：

  Bromination of alkenes in acetonitrile. A rate and product study

  摘要：

  The reaction of simple alkenes and aryl alkenes with molecular bromine in damp MeCN occurred with solvent incorporation to give 2-bromo-1-(N-acetylamino)alkanes, 2-methyloxazolines, 2-acetoxyalkylamine hydrobromides, and 2-(N-acetylamino) alcohols. These products arose by the transformation of initially formed 2-bromo-1-(N-acetylamino)alkanes obtained by MeCN attack on bromonium or bromocarbonium ions to give nitrilium tribromide salts. These reacted with water to give 2-bromo-1-(N-acetylamino)alkanes. The kinetic profile of the reaction showed a very fast initial reaction of the alkene and Br2 to yield the nitrilium tribromide, followed by a much slower reaction of Br3- with the alkene. The incorporation of MeCN was Markovnikov and stereospecifically anti. The degree to which incorporation of solvent occurred depended upon the alkene structure and the initial reagent concentrations. A rationalization for the observed chemoselectivity and its dependence on the reaction conditions is offered.

  DOI：

  10.1021/jo00009a027
• 作为产物：
  描述：

  苯乙烯 、 乙腈 在 水 、 溴 作用下， 反应 0.33h， 以12%的产率得到2-acetoxy-1-phenylethylamine hydrobromide
  参考文献：
  名称：

  Bromination of alkenes in acetonitrile. A rate and product study

  摘要：

  The reaction of simple alkenes and aryl alkenes with molecular bromine in damp MeCN occurred with solvent incorporation to give 2-bromo-1-(N-acetylamino)alkanes, 2-methyloxazolines, 2-acetoxyalkylamine hydrobromides, and 2-(N-acetylamino) alcohols. These products arose by the transformation of initially formed 2-bromo-1-(N-acetylamino)alkanes obtained by MeCN attack on bromonium or bromocarbonium ions to give nitrilium tribromide salts. These reacted with water to give 2-bromo-1-(N-acetylamino)alkanes. The kinetic profile of the reaction showed a very fast initial reaction of the alkene and Br2 to yield the nitrilium tribromide, followed by a much slower reaction of Br3- with the alkene. The incorporation of MeCN was Markovnikov and stereospecifically anti. The degree to which incorporation of solvent occurred depended upon the alkene structure and the initial reagent concentrations. A rationalization for the observed chemoselectivity and its dependence on the reaction conditions is offered.

  DOI：

  10.1021/jo00009a027