(1R,2S,4R,13bS)-2-ethyl-2,3,4,5,7,8-hexahydro-10-methoxy-13H,4,13b-methano-1H-azepino<1',2':1,2>pyrido<3,4-b>indol-1-ol acetate | 223513-08-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1R,2S,4R,13bS)-2-ethyl-2,3,4,5,7,8-hexahydro-10-methoxy-13H,4,13b-methano-1H-azepino<1',2':1,2>pyrido<3,4-b>indol-1-ol acetate
• 英文别名: [(1S,15R,17S,18R)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.01,13.02,10.04,9]nonadeca-2(10),4(9),5,7-tetraen-18-yl] acetate
• CAS: 223513-08-4
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: SSBOPRURXVHMGA-LZCMIUFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,13bS)-2-ethyl-2,3,4,5,7,8-hexahydro-10-methoxy-13H,4,13b-methano-1H-azepino<1',2':1,2>pyrido<3,4-b>indol-1-ol acetate 在 水 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以49%的产率得到12-methoxyibogamin-5-ol
  参考文献：
  名称：

  A New Rearrangement inIboga Alkaloids

  摘要：

  The hydroxyindolenine 2, upon treatment with Ac2O in pyridine, rearranged into the bridged 16-spiro compound 3. Compound 3 can be considered to be a synthon of the carbocation at C(16) of ibogaine (7) since the solvolysis of 3 in EtOH/H2O gave a mixture of the 16-ethoxy- and 16-hydroxyibogaine derivatives 5 and 6, respectively.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<170::aid-hlca170>3.0.co;2-0
• 作为产物：
  描述：

  乙酸酐 、 (7S)-ibogaine hydroxyindolenine 在 吡啶 作用下， 以42%的产率得到(1R,2S,4R,13bS)-2-ethyl-2,3,4,5,7,8-hexahydro-10-methoxy-13H,4,13b-methano-1H-azepino<1',2':1,2>pyrido<3,4-b>indol-1-ol acetate
  参考文献：
  名称：

  A New Rearrangement inIboga Alkaloids

  摘要：

  The hydroxyindolenine 2, upon treatment with Ac2O in pyridine, rearranged into the bridged 16-spiro compound 3. Compound 3 can be considered to be a synthon of the carbocation at C(16) of ibogaine (7) since the solvolysis of 3 in EtOH/H2O gave a mixture of the 16-ethoxy- and 16-hydroxyibogaine derivatives 5 and 6, respectively.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<170::aid-hlca170>3.0.co;2-0