(3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol | 193604-42-1

• 英文名称: (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol
• CAS: 193604-42-1
• 化学式: C₁₉H₂₂N₂O
• 分子量: 294.396
• InChiKey: MKOSHZRCNAVIGT-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  26.71
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol 在 palladium dihydroxide 氢气 、 sodium 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.67h， 生成 (-)-norphysostigmine
  参考文献：
  名称：

  Total Syntheses and Anticholinesterase Activities of (3aS)-N(8)-Norphysostigmine, (3aS)-N(8)-Norphenserine, Their Antipodal Isomers, and Other N(8)-Substituted Analogues

  摘要：

  N(8)-Benzylesermethole (6) was prepared from 5-methoxytryptamine (1) in five steps. Resolution of compound 6 by dibenzoyl- and ditoluyltartaric acid provided enantiomers (-)- and (+)-7. After demethylation, reaction with isocyanates and catalytic debenzylation over hydrogen, the total syntheses of(-)-and (+)-N(8)-norphysostigmine [(-)-and (+)-11] and (-)-and (+)N(8)-norphenserine [(-)-and (+)-12] were accomplished. (-)-N(8)-Norphysostigmine [(-)-11] and (-)-N(8)-norphenserine [(-)-12] were also obtained by transformations of natural physostigmine [(-)-13] and phenserine [(-)-14] prepared from(-)-13. The absolute configurations and optical purity of compounds (-)-11, (-)-12, (+)-11, and (+)-12 were confirmed by a comparison of their optical rotations with those of the compounds synthesized from physostigmine [(-)-13]. The anticholinesterase activities of N(8)-nor-and N(8)-substituted analogues, (-)-and (+)-9, -10, -11, -12, 15, and 16, were compared with those of physostigmine [(-)-and (+)-13] and phenserine [(-)- and (+)-14] and are reported.

  DOI：

  10.1021/jm970210v
• 作为产物：
  描述：

  5-甲氧基色胺 在 盐酸 、 sodium hydroxide 、 三溴化硼 、 苄基三甲基溴化铵 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 红铝 作用下， 以 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 14.66h， 生成 (3aS,8aR)-8-Benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-ol
  参考文献：
  名称：

  Total Syntheses and Anticholinesterase Activities of (3aS)-N(8)-Norphysostigmine, (3aS)-N(8)-Norphenserine, Their Antipodal Isomers, and Other N(8)-Substituted Analogues

  摘要：

  N(8)-Benzylesermethole (6) was prepared from 5-methoxytryptamine (1) in five steps. Resolution of compound 6 by dibenzoyl- and ditoluyltartaric acid provided enantiomers (-)- and (+)-7. After demethylation, reaction with isocyanates and catalytic debenzylation over hydrogen, the total syntheses of(-)-and (+)-N(8)-norphysostigmine [(-)-and (+)-11] and (-)-and (+)N(8)-norphenserine [(-)-and (+)-12] were accomplished. (-)-N(8)-Norphysostigmine [(-)-11] and (-)-N(8)-norphenserine [(-)-12] were also obtained by transformations of natural physostigmine [(-)-13] and phenserine [(-)-14] prepared from(-)-13. The absolute configurations and optical purity of compounds (-)-11, (-)-12, (+)-11, and (+)-12 were confirmed by a comparison of their optical rotations with those of the compounds synthesized from physostigmine [(-)-13]. The anticholinesterase activities of N(8)-nor-and N(8)-substituted analogues, (-)-and (+)-9, -10, -11, -12, 15, and 16, were compared with those of physostigmine [(-)-and (+)-13] and phenserine [(-)- and (+)-14] and are reported.

  DOI：

  10.1021/jm970210v