(3aS,7aR)-3a-(3,4-dimethoxyphenyl)-1-[(R)-1-(1,2,3,4-tetrahydronaphthalen-5-yl)ethyl]octahydroindol-2-one | 943229-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aS,7aR)-3a-(3,4-dimethoxyphenyl)-1-[(R)-1-(1,2,3,4-tetrahydronaphthalen-5-yl)ethyl]octahydroindol-2-one
• 英文别名: (3aS,7aR)-3a-(3,4-dimethoxyphenyl)-1-[(1R)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethyl]-3,4,5,6,7,7a-hexahydroindol-2-one
• CAS: 943229-26-3
• 化学式: C₂₈H₃₅NO₃
• 分子量: 433.591
• InChiKey: LMRAJVGYXBMSQX-YPLOMLCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,7aR)-3a-(3,4-dimethoxyphenyl)-1-[(R)-1-(1,2,3,4-tetrahydronaphthalen-5-yl)ethyl]octahydroindol-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以74%的产率得到(3aS,7aR)-3a-(3,4-dimethoxyphenyl)-1-[(R)-1-(1,2,3,4-tetrahydronaphthalen-5-yl)ethyl]octahydroindole
  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-(3,4-dimethoxyphenyl)cyclohexanone 在 platinum(IV) oxide 、 镍 4-二甲氨基吡啶 、 氢气 、 对甲苯磺酸 、 N,N-二甲基苯胺 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 35.08h， 生成 (3aS,7aR)-3a-(3,4-dimethoxyphenyl)-1-[(R)-1-(1,2,3,4-tetrahydronaphthalen-5-yl)ethyl]octahydroindol-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

文献信息

• Saito, Miho; Matsuo, Jun-ichi; Uchiyama, Masahiko, Heterocycles, 2006, vol. 69, # 1, p. 69 - 72
  作者：Saito, Miho、Matsuo, Jun-ichi、Uchiyama, Masahiko、Ishibashi, Hiroyuki

  DOI：——

  日期：——
• Stereoselective synthesis of cis and trans-fused 3a-aryloctahydroindoles using cyclization of N-vinylic α-(methylthio)acetamides: synthesis of (−)-mesembrane
  作者：Miho Saito、Jun-ichi Matsuo、Hiroyuki Ishibashi

  DOI：10.1016/j.tet.2007.03.153

  日期：2007.6

  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.