cis-3-ethyl-4a-(carbamoylmethyl)-9-benzylhexahydrocarbazol-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: cis-3-ethyl-4a-(carbamoylmethyl)-9-benzylhexahydrocarbazol-4-one
• 化学式: C₂₃H₂₆N₂O₂
• 分子量: 362.472
• InChiKey: YKLTWPXLFLIOKZ-BININLDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-3-ethyl-4a-(carbamoylmethyl)-9-benzylhexahydrocarbazol-4-one 在 camphor-10-sulfonic acid 作用下， 以 苯 为溶剂， 反应 10.0h， 以92%的产率得到20-ethyl-5-oxo-1-benzylhexahydropyrrolocarbazole
  参考文献：
  名称：

  Unexpected Results in the Reduction of Tetracyclic Enamides. Structure, Stereochemistry and Conformation of a 20b-Hydroperoxyimine

  摘要：

  Reduction of N(b)-allyl-20-ethyltetracyclic enamide (7) with lithium aluminium hydride afforded the expected enamine (12) and 4a-oxoethylhexahydrocarbazolones (18a,b). Reduction of N(b)-unsubstituted enamide (6), under the same conditions, gave imine (9), enamine (11) and a 20beta-hydroperoxytetracyclic imine (19) resulting from the peroxydation of 9 and 11. The C-20 stereochemistry of 19 was established by means of 2D H-1 nmr and NOE difference spectroscopy.

  DOI：

  10.3987/com-94-6767
• 作为产物：
  描述：

  2-碘乙酰胺 、 在 potassium hydride 作用下， 生成 21-hydroxy-20-ethyl-5-oxo-1-benzyloctahydropyrrolocarbazole 、 cis-3-ethyl-4a-(carbamoylmethyl)-9-benzylhexahydrocarbazol-4-one
  参考文献：
  名称：

  Unexpected Results in the Reduction of Tetracyclic Enamides. Structure, Stereochemistry and Conformation of a 20b-Hydroperoxyimine

  摘要：

  Reduction of N(b)-allyl-20-ethyltetracyclic enamide (7) with lithium aluminium hydride afforded the expected enamine (12) and 4a-oxoethylhexahydrocarbazolones (18a,b). Reduction of N(b)-unsubstituted enamide (6), under the same conditions, gave imine (9), enamine (11) and a 20beta-hydroperoxytetracyclic imine (19) resulting from the peroxydation of 9 and 11. The C-20 stereochemistry of 19 was established by means of 2D H-1 nmr and NOE difference spectroscopy.

  DOI：

  10.3987/com-94-6767

文献信息

• Unexpected Results in the Reduction of Tetracyclic Enamides. Structure, Stereochemistry and Conformation of a 20b-Hydroperoxyimine
  作者：Denis Dugat、G屍ard Dauphin、Jean-Claude Gramain

  DOI：10.3987/com-94-6767

  日期：——

  Reduction of N(b)-allyl-20-ethyltetracyclic enamide (7) with lithium aluminium hydride afforded the expected enamine (12) and 4a-oxoethylhexahydrocarbazolones (18a,b). Reduction of N(b)-unsubstituted enamide (6), under the same conditions, gave imine (9), enamine (11) and a 20beta-hydroperoxytetracyclic imine (19) resulting from the peroxydation of 9 and 11. The C-20 stereochemistry of 19 was established by means of 2D H-1 nmr and NOE difference spectroscopy.