18β-hydroxyvincamine | 68346-04-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Eburnan型生物碱
• 英文名称: 18β-hydroxyvincamine
• 英文别名: methyl (13S,15S,17S,19S)-15-ethyl-13,17-dihydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• CAS: 68346-04-3
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: ZDYLDNUNSYRXBU-PMVWVRLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  18β-hydroxyvincamine 在 sodium dichromate 、 sodium tetrahydroborate 作用下， 以 溶剂黄146 、 甲醇 为溶剂， 反应 21.0h， 以10%的产率得到trans 18β-hydroxy-3-epi-14-epivincamine
  参考文献：
  名称：

  Synthesis of 18-Hydroxyvincamines and Epoxy-1,14-secovincamines; a New Proof for the Aspidospermane-Eburnane Rearrangement

  摘要：

  Chemical transformations started from tabersonine were studied. A one-pot oxidative ring-transformation with permaleic acid in methanol yielded 17,18-dehydrovincamine. Hydroboration-oxidation of the latter compound led to alkaloid 17,18-dehydrovincamone. Hydroboration-oxidation of tabersonine resulted 14 beta-hydroxyvineadifformine and 15p-hydroxyvincadifforinine. Allowing 14 beta- and 15 beta- hydroxyvincadifformines to react with permaleic acid/methanol provided 1,14-secovincamines, serving as new evidence for the mechanism of the aspidospermane-eburnane transformation. On the other hand 18 beta-hydroxyvincamine was obtained from 14 beta-hydroxyvincadifformine by reaction with 3-chloroperbenzoic acid and successive treatment with triphenylphosphine/aqueous acetic acid.

  DOI：

  10.3987/com-07-11114
• 作为产物：
  描述：

  (-)-14β-hydroxyvincadifformine 在 间氯过氧苯甲酸 、 溶剂黄146 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 17.5h， 以49.6%的产率得到18β-hydroxyvincamine
  参考文献：
  名称：

  Synthesis of 18-Hydroxyvincamines and Epoxy-1,14-secovincamines; a New Proof for the Aspidospermane-Eburnane Rearrangement

  摘要：

  Chemical transformations started from tabersonine were studied. A one-pot oxidative ring-transformation with permaleic acid in methanol yielded 17,18-dehydrovincamine. Hydroboration-oxidation of the latter compound led to alkaloid 17,18-dehydrovincamone. Hydroboration-oxidation of tabersonine resulted 14 beta-hydroxyvineadifformine and 15p-hydroxyvincadifforinine. Allowing 14 beta- and 15 beta- hydroxyvincadifformines to react with permaleic acid/methanol provided 1,14-secovincamines, serving as new evidence for the mechanism of the aspidospermane-eburnane transformation. On the other hand 18 beta-hydroxyvincamine was obtained from 14 beta-hydroxyvincadifformine by reaction with 3-chloroperbenzoic acid and successive treatment with triphenylphosphine/aqueous acetic acid.

  DOI：

  10.3987/com-07-11114

文献信息

• Synthesis of 18-Hydroxyvincamines and Epoxy-1,14-secovincamines; a New Proof for the Aspidospermane-Eburnane Rearrangement
  作者：András Nemes、Csaba Szántay、László Czibula、István Greiner

  DOI：10.3987/com-07-11114

  日期：——

  Chemical transformations started from tabersonine were studied. A one-pot oxidative ring-transformation with permaleic acid in methanol yielded 17,18-dehydrovincamine. Hydroboration-oxidation of the latter compound led to alkaloid 17,18-dehydrovincamone. Hydroboration-oxidation of tabersonine resulted 14 beta-hydroxyvineadifformine and 15p-hydroxyvincadifforinine. Allowing 14 beta- and 15 beta- hydroxyvincadifformines to react with permaleic acid/methanol provided 1,14-secovincamines, serving as new evidence for the mechanism of the aspidospermane-eburnane transformation. On the other hand 18 beta-hydroxyvincamine was obtained from 14 beta-hydroxyvincadifformine by reaction with 3-chloroperbenzoic acid and successive treatment with triphenylphosphine/aqueous acetic acid.