16,17-dinor-corynan-19-ol | 65601-22-1

• 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: 16,17-dinor-corynan-19-ol
• 英文别名: 3α-(1ξ-Hydroxy-ethyl)-1,2,3,4,6,7,12,12bα-octahydro-indolo<2.3-a>chinolizin；3α-(1ξ-Hydroxy-ethyl)-1,2,3,4,6,7,12,12bα-octahydro-indolo[2.3-a]chinolizin
• CAS: 65601-22-1；112530-54-8；112530-55-9；115887-65-5；115887-66-6
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: IWBANHMNZOIFLA-KMQIDDJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  39.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 16,17-dinor-corynan-19-ol 在 吡啶 作用下， 反应 4.0h， 以80%的产率得到Acetic acid (3R,12bS)-1-(1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-3-yl)-ethyl ester
  参考文献：
  名称：

  Mandal, Sukhendu B.; Pakrashi, Satyesh C., Heterocycles, 1987, vol. 26, # 6, p. 1557 - 1562

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S)-1-[(3R,12bR)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl]ethanol 以 磷酸 为溶剂， 反应 3.0h， 以60%的产率得到16,17-dinor-corynan-19-ol
  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

文献信息

• Reduction of lactams and thiolactams by sodium borohydride. Application in the synthesis of some alkaloids
  作者：S. B. Mandal、V. S. Giri、M. S. Sabeena、S. C. Pakrashi

  DOI：10.1021/jo00253a014

  日期：1988.9
• Mandal, Sukhendu B.; Pakrashi, Satyesh C., Heterocycles, 1987, vol. 26, # 6, p. 1557 - 1562
  作者：Mandal, Sukhendu B.、Pakrashi, Satyesh C.

  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.