(3aR,7aR)-octahydro-1-[(S)-1-(1-naphthyl)ethyl]indol-2-one | 183477-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3aR,7aR)-octahydro-1-[(S)-1-(1-naphthyl)ethyl]indol-2-one
• 英文别名: (3aR,7aR)-1-[(1S)-1-naphthalen-1-ylethyl]-3a,4,5,6,7,7a-hexahydro-3H-indol-2-one
• CAS: 183477-39-6
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: NCEALRYZGSXWEK-ZSZQSSIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3aR,7aR)-octahydro-1-[(S)-1-(1-naphthyl)ethyl]indol-2-one 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (3aR,7aR)-octahydroindol-2-one
  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 、 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 29.0h， 生成 (3aR,7aR)-octahydro-1-[(S)-1-(1-naphthyl)ethyl]indol-2-one
  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

文献信息

• Radical cyclization of chiral N-(1-cycloalken-1-yl)-α-haloacetamides: Synthesis of optically active bicyclic pyrrolidinones
  作者：Hiroyuki Ishibashi、Yumi Fuke、Takashi Yamashita、Masazumi Ikeda

  DOI：10.1016/0957-4166(96)00326-6

  日期：1996.9

  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