benzyl N-[(10R,11R,15R,19S)-17-oxo-6-phenylmethoxy-1-azapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraen-10-yl]carbamate | 133715-11-4

• 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: benzyl N-[(10R,11R,15R,19S)-17-oxo-6-phenylmethoxy-1-azapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraen-10-yl]carbamate
• CAS: 133715-11-4
• 化学式: C₃₃H₃₂N₂O₄
• 分子量: 520.628
• InChiKey: JDDJTPZKLHIXDF-HVHHDALESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-[(10R,11R,15R,19S)-17-oxo-6-phenylmethoxy-1-azapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraen-10-yl]carbamate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 以65.7%的产率得到(3aR,12R,12aR,12bS)-12-amino-2,3,3a,4,11,12,12a,12b-octahydro-10-hydroxyisoquino<2,1,8-lma>carbazol-5(1H)-one hydrochloride
  参考文献：
  名称：

  Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

  摘要：

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00199-1
• 作为产物：
  描述：

  2-iodo-1-cyclohexanol 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 sodium azide 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 硝苯酚 作用下， 以 甲醇 、 异丙醚 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 68.5h， 生成 benzyl N-[(10R,11R,15R,19S)-17-oxo-6-phenylmethoxy-1-azapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2(7),3,5,8(18)-tetraen-10-yl]carbamate
  参考文献：
  名称：

  Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

  摘要：

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00199-1

文献信息

• Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification
  作者：Tetuya Fukazawa、Yasuo Shimoji、Toshihiko Hashimoto

  DOI：10.1016/0957-4166(96)00199-1

  日期：1996.6

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd