[(3aR,8bS)-4-benzyl-3,8b-dimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate | 193604-44-3

• 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: [(3aR,8bS)-4-benzyl-3,8b-dimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate
• CAS: 193604-44-3
• 化学式: C₂₆H₂₇N₃O₂
• 分子量: 413.519
• InChiKey: UUQLGETXWSEMFB-RSXGOPAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3aR,8bS)-4-benzyl-3,8b-dimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以64.7%的产率得到(-)-N8-norphenylcarbamoyleseroline
  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 、 sodium 、 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 乙醚 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 14.66h， 生成 [(3aR,8bS)-4-benzyl-3,8b-dimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate
  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

文献信息

• Total Syntheses and Anticholinesterase Activities of (3a<i>S</i>)-<i>N</i>(8)-Norphysostigmine, (3a<i>S</i>)-<i>N</i>(8)-Norphenserine, Their Antipodal Isomers, and Other <i>N</i>(8)-Substituted Analogues
  作者：Qian-sheng Yu、Xue-Feng Pei、Harold W. Holloway、Nigel H. Greig、Arnold Brossi

  DOI：10.1021/jm970210v

  日期：1997.8.1

  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.