2-bromo-N-(1-cyclohexen-1-yl)-N-[(S)-1-(1-naphthyl)ethyl]acetamide | 183477-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-bromo-N-(1-cyclohexen-1-yl)-N-[(S)-1-(1-naphthyl)ethyl]acetamide
• CAS: 183477-36-3
• 化学式: C₂₀H₂₂BrNO
• 分子量: 372.305
• InChiKey: MKLZMTCVBBDJSQ-HNNXBMFYSA-N

物化性质

• 沸点：
  519.7±49.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(1-cyclohexen-1-yl)-N-[(S)-1-(1-naphthyl)ethyl]acetamide 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以82%的产率得到N-(1-cyclohexen-1-yl)-2-iodo-N-[(S)-1-(1-naphthyl)ethyl]acetamide
  参考文献：
  名称：

  Radical cyclization of chiral N-(1-cycloalken-1-yl)-α-haloacetamides: Synthesis of optically active bicyclic pyrrolidinones

  摘要：

  Asymmetric induction in the 5-endo-trig radical cyclization of N-(1-cycloallren-1-yl> a-haloacetamides has been examined. alpha-Iodo amide 7 bearing an (S)-1-(1-naphthyl)ethyl group on the nitrogen afforded a 92:8 mixture of bicyclic lactams 9a,b, which was transformed into (3aR,7aR)-octahydroindol-2-one 10a in 77% ee. alpha-Bromo amide 11 bearing an N-(R)-1-phenethyl group provided a 61:39 mixture of 13a,b. The major product 13a was then transformed into enantiomerically pure (1S,5S)-2-azabicyclo[3.3.0]octan-3-one 15. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00326-6
• 作为产物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 2-bromo-N-(1-cyclohexen-1-yl)-N-[(S)-1-(1-naphthyl)ethyl]acetamide
  参考文献：
  名称：

  Radical cyclization of chiral N-(1-cycloalken-1-yl)-α-haloacetamides: Synthesis of optically active bicyclic pyrrolidinones

  摘要：

  Asymmetric induction in the 5-endo-trig radical cyclization of N-(1-cycloallren-1-yl> a-haloacetamides has been examined. alpha-Iodo amide 7 bearing an (S)-1-(1-naphthyl)ethyl group on the nitrogen afforded a 92:8 mixture of bicyclic lactams 9a,b, which was transformed into (3aR,7aR)-octahydroindol-2-one 10a in 77% ee. alpha-Bromo amide 11 bearing an N-(R)-1-phenethyl group provided a 61:39 mixture of 13a,b. The major product 13a was then transformed into enantiomerically pure (1S,5S)-2-azabicyclo[3.3.0]octan-3-one 15. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00326-6