<3α(R^*),12bα>-(+/-)-1,2,3,4,6,7,12,12b-Octahydro-α-methylindolo<2,3-a>quinolizine-3-methanol

• 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: <3α(R^*),12bα>-(+/-)-1,2,3,4,6,7,12,12b-Octahydro-α-methylindolo<2,3-a>quinolizine-3-methanol
• 英文别名: (1R)-1-[(3R,12bS)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl]ethanol
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: IWBANHMNZOIFLA-HSMVNMDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <3α(R^*),12bα>-(+/-)-1,2,3,4,6,7,12,12b-Octahydro-α-methylindolo<2,3-a>quinolizine-3-methanol 在 phosphorus pentoxide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以13%的产率得到(+/-)-deplancheine
  参考文献：
  名称：

  Synthesis and Conformational Study of Indolo[2,3-a]quinolizidine-3-ethan-1'-ols: Intermediates for the Synthesis of Deplancheine and Flavopereirine

  摘要：

  The synthesis and stereostructures of all four indolo[2,3-a]quinolizidine-3-ethan-1'-ols are described. The two alcohols with an axial side chain exist principally in the conformation where the C/D ring junction is trans, which is favoured by an intramolecular hydrogen bond between the hydroxyl group and the N-b-atom. Dehydration of the four alcohols with P2O5 in each case led to a mixture consisting of E-deplancheine and Z-deplancheine. The three side products were two 3-vinyl isomers, one of which can be converted to deplancheine via double bond isomerization, and 3-ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine, which is a precursor of flavopereirine.

  DOI：

  10.3987/com-97-7816
• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 铂 盐酸 、 sodium tetrahydroborate 、 mercury(II) diacetate 、 氢气 、 edetate disodium 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.5h， 生成 <3α(R^*),12bα>-(+/-)-1,2,3,4,6,7,12,12b-Octahydro-α-methylindolo<2,3-a>quinolizine-3-methanol
  参考文献：
  名称：

  Fujii, Tozo; Ohba, Masashi; Sasaki, Noriko, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 10, p. 2822 - 2824

  摘要：

  DOI：

文献信息

• Fujii, Tozo; Ohba, Masashi; Sasaki, Noriko, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 10, p. 2822 - 2824
  作者：Fujii, Tozo、Ohba, Masashi、Sasaki, Noriko

  DOI：——

  日期：——
• Synthesis and Conformational Study of Indolo[2,3-a]quinolizidine-3-ethan-1'-ols: Intermediates for the Synthesis of Deplancheine and Flavopereirine
  作者：Mauri Lounasmaa、Kimmo Karinen、Arto Tolvanen

  DOI：10.3987/com-97-7816

  日期：——

  The synthesis and stereostructures of all four indolo[2,3-a]quinolizidine-3-ethan-1'-ols are described. The two alcohols with an axial side chain exist principally in the conformation where the C/D ring junction is trans, which is favoured by an intramolecular hydrogen bond between the hydroxyl group and the N-b-atom. Dehydration of the four alcohols with P2O5 in each case led to a mixture consisting of E-deplancheine and Z-deplancheine. The three side products were two 3-vinyl isomers, one of which can be converted to deplancheine via double bond isomerization, and 3-ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine, which is a precursor of flavopereirine.