(3aS,8aR)-1-Benzyl-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indol-5-one | 290294-27-8

• 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: (3aS,8aR)-1-Benzyl-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indol-5-one
• 英文别名: (3aR,8bS)-3-benzyl-8b-methyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-one
• CAS: 290294-27-8
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: QZEHZYLMDJVKJB-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,8aR)-1-Benzyl-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indol-5-one 在 palladium dihydroxide sodium tetrahydroborate 、 氢气 、 sodium 作用下， 以 四氢呋喃 、 乙醚 、 异丙醇 为溶剂， 生成 (-)-N¹,N⁸-bisnorcymserine
  参考文献：
  名称：

  A practical conversion of natural physostigmine into the potent butyrylcholinesterase inhibitor N1,N8-bisnorcymserine

  摘要：

  A rapid novel synthetic route to the potent reversible butyrylcholinesterase inhibitor (-)-N-1,N-8-bis-norcymserine (1) is reported from physostigmine (2) in a 20% total yield. Details on the formation of the imino-quinone 6 obtained in the oxidation of N-1-benzylnoresermethole (4) and its conversion into N-1-bis-noreseroline (7) are given. As expected, the product of this synthesis, (1), had identical biological activity to the same agent produced by total synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00740-1
• 作为产物：
  描述：

  氧化毒扁豆碱 在 氢氧化钾 、 重铬酸吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (3aS,8aR)-1-Benzyl-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indol-5-one
  参考文献：
  名称：

  A practical conversion of natural physostigmine into the potent butyrylcholinesterase inhibitor N1,N8-bisnorcymserine

  摘要：

  A rapid novel synthetic route to the potent reversible butyrylcholinesterase inhibitor (-)-N-1,N-8-bis-norcymserine (1) is reported from physostigmine (2) in a 20% total yield. Details on the formation of the imino-quinone 6 obtained in the oxidation of N-1-benzylnoresermethole (4) and its conversion into N-1-bis-noreseroline (7) are given. As expected, the product of this synthesis, (1), had identical biological activity to the same agent produced by total synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00740-1

文献信息

• A practical conversion of natural physostigmine into the potent butyrylcholinesterase inhibitor N1,N8-bisnorcymserine
  作者：Xiaoxiang Zhu、Nigel H Greig、Harold W Holloway、Noel F Whittaker、Arnold Brossi、Qian-sheng Yu

  DOI：10.1016/s0040-4039(00)00740-1

  日期：2000.6

  A rapid novel synthetic route to the potent reversible butyrylcholinesterase inhibitor (-)-N-1,N-8-bis-norcymserine (1) is reported from physostigmine (2) in a 20% total yield. Details on the formation of the imino-quinone 6 obtained in the oxidation of N-1-benzylnoresermethole (4) and its conversion into N-1-bis-noreseroline (7) are given. As expected, the product of this synthesis, (1), had identical biological activity to the same agent produced by total synthesis. (C) 2000 Elsevier Science Ltd. All rights reserved.