2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20α,21α) | 77080-80-9

• 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: 2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20α,21α)
• CAS: 77080-80-9
• 化学式: C₂₉H₃₄N₂O₄
• 分子量: 474.6
• InChiKey: BHNMEPDNEYYHTH-MPFGFTFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20α,21α) 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 methyl (1S,12R,19R)-12-ethyl-15-oxo-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate
  参考文献：
  名称：

  Studies in biomimetic alkaloid syntheses. 6. Alternative pathways to secodines and their acyclic enamino acrylate analogs. Total syntheses of desethylibophyllidine, D-norvincadifformine, desethylvincadifformine, 20-methyldesethylvincadifformine, and 3-oxovincadifformine

  摘要：

  DOI：

  10.1021/jo00323a007
• 作为产物：
  描述：

  溴甲苯 、 methyl 1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5-carboxylate 在 N,N-二异丙基乙胺 作用下， 生成 2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20α,21α) 、 2,16-didehydro-3-phenyl-14,16-bis(methoxycarbonyl)-3,14-secoaspidospermidine (20β,21α)
  参考文献：
  名称：

  Studies in biomimetic alkaloid syntheses. 6. Alternative pathways to secodines and their acyclic enamino acrylate analogs. Total syntheses of desethylibophyllidine, D-norvincadifformine, desethylvincadifformine, 20-methyldesethylvincadifformine, and 3-oxovincadifformine

  摘要：

  DOI：

  10.1021/jo00323a007

文献信息

• Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (.+-.)-vincadifformine, (.+-.)-tabersonine, and (.+-.)-oxotabersonine
  作者：Gyorgy Kalaus、Istvan Greiner、Maria Kajtar-Peredy、Janos Brlik、Lajos Szabo、Csaba Szantay

  DOI：10.1021/jo00058a025

  日期：1993.3

  Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.
• Formation of D-nor aspidosperma alkaloids by condensation of Nb-benzylindoloazepine with aldehydes
  作者：Martin E. Kuehne、Stephen E. Kuehne

  DOI：10.1021/jo00067a061

  日期：1993.7
• Studies in biomimetic alkaloid syntheses. 6. Alternative pathways to secodines and their acyclic enamino acrylate analogs. Total syntheses of desethylibophyllidine, D-norvincadifformine, desethylvincadifformine, 20-methyldesethylvincadifformine, and 3-oxovincadifformine
  作者：Martin E. Kuehne、Thomas H. Matsko、John C. Bohnert、Linda Motyka、David Oliver-Smith

  DOI：10.1021/jo00323a007

  日期：1981.5