N-[(1S,2R)-2-hydroxycycloheptyl]acetamide | 133649-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(1S,2R)-2-hydroxycycloheptyl]acetamide
• CAS: 133649-14-6
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: WHRMGZGGPOLVIE-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环庚烯 在 sodium hydroxide 、 水 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 N-[(1S,2R)-2-hydroxycycloheptyl]acetamide
  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