α-(methylthio)-N-[(R)-1-(1-naphthyl)-ethyl]-N-(2-phenylcyclohexen-1-yl)acetamide | 943229-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: α-(methylthio)-N-[(R)-1-(1-naphthyl)-ethyl]-N-(2-phenylcyclohexen-1-yl)acetamide
• CAS: 943229-18-3
• 化学式: C₂₇H₂₉NOS
• 分子量: 415.599
• InChiKey: VTIWKPBRJWIKMQ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α-(methylthio)-N-[(R)-1-(1-naphthyl)-ethyl]-N-(2-phenylcyclohexen-1-yl)acetamide 在 镍 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 1.0h， 生成 2,3,3a,4,5,6-hexahydro-1-[(R)-1-(1-naphthyl)ethyl]-3a-phenylindole-2-one
  参考文献：
  名称：

  Stereoselective synthesis of cis and trans-fused 3a-aryloctahydroindoles using cyclization of N-vinylic α-(methylthio)acetamides: synthesis of (−)-mesembrane

  摘要：

  Treatment of N-(2-arylcyclohex-1-en-1-yl)-alpha-(methylthio)acetamides with N-chlorosuccinimide (NCS) gave 3a-aryl-2,3,3a,4, 5,6-hexahydro-3-(methylthio)indol-2-ones. Desulfurization of the cyclization products followed by a catalytic hydrogenation of the resulting hexahydroindol-2-ones gave predominantly or exclusively trans-fused octahydroindol-2-ones. On the other hand, reduction of the desulfurization products with Et3SiH in CF3CO2H exclusively provided cis-fused octahydroindol-2-ones. A chiral induction of N-[2-(3,4-dimethoxy)phenylcyclohex-1-en-1-yl]-alpha-(methylthio)acetamide having an (R)-1-(l-naphthyl)ethyl group on the nitrogen atom led to the synthesis of (-)-mesembrane and (-)-trans-mesembrane. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.153
• 作为产物：
  描述：

  2-苯基环己酮 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N-二甲基苯胺 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 α-(methylthio)-N-[(R)-1-(1-naphthyl)-ethyl]-N-(2-phenylcyclohexen-1-yl)acetamide
  参考文献：
  名称：

  Stereoselective synthesis of cis and trans-fused 3a-aryloctahydroindoles using cyclization of N-vinylic α-(methylthio)acetamides: synthesis of (−)-mesembrane

  摘要：

  Treatment of N-(2-arylcyclohex-1-en-1-yl)-alpha-(methylthio)acetamides with N-chlorosuccinimide (NCS) gave 3a-aryl-2,3,3a,4, 5,6-hexahydro-3-(methylthio)indol-2-ones. Desulfurization of the cyclization products followed by a catalytic hydrogenation of the resulting hexahydroindol-2-ones gave predominantly or exclusively trans-fused octahydroindol-2-ones. On the other hand, reduction of the desulfurization products with Et3SiH in CF3CO2H exclusively provided cis-fused octahydroindol-2-ones. A chiral induction of N-[2-(3,4-dimethoxy)phenylcyclohex-1-en-1-yl]-alpha-(methylthio)acetamide having an (R)-1-(l-naphthyl)ethyl group on the nitrogen atom led to the synthesis of (-)-mesembrane and (-)-trans-mesembrane. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.153