假蟾毒胺醇 | 113056-55-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 中文名称: 假蟾毒胺醇
• 英文名称: (+)-pseudophrynaminol
• 英文别名: (E)-4-[(3aR,8bR)-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl]-2-methylbut-2-en-1-ol
• CAS: 113056-55-6
• 化学式: C₁₆H₂₂N₂O
• 分子量: 258.363
• InChiKey: YUFJTBNXHFFQKN-PWEFJHHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+)-(3aR,8aS)-1-methyl-3a-<1-(4-hydroxy-3-methyl-2E-butenyl)>-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2.3-b>indole 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以77%的产率得到假蟾毒胺醇
  参考文献：
  名称：

  The chemistry of cyclic tautomers of tryptophan: Total synthesis of (+)-(ent)-pseudophrynaminol

  摘要：

  A diastereoselective synthesis of the unnatural (+)-enantiomer of the hexahydropyrroloindole alkaloid (-)-pseudophrynaminol (3), isolated from the skin of the Australian frog Pseudophryne coriacea, from a cyclic tautomer (1) of L-tryptophan, is described, The CD spectrum of the synthetic 3 is opposite in sign to that of the natural material enabling the configuration of the natural product to be established as 3aS,8aR.

  DOI：

  10.1016/0040-4020(95)00307-t

文献信息

• The chemistry of cyclic tautomers of tryptophan: Total synthesis of (+)-(ent)-pseudophrynaminol
  作者：David Crich、Anna B. Pavlovic、Raghu Samy

  DOI：10.1016/0040-4020(95)00307-t

  日期：1995.6

  A diastereoselective synthesis of the unnatural (+)-enantiomer of the hexahydropyrroloindole alkaloid (-)-pseudophrynaminol (3), isolated from the skin of the Australian frog Pseudophryne coriacea, from a cyclic tautomer (1) of L-tryptophan, is described, The CD spectrum of the synthetic 3 is opposite in sign to that of the natural material enabling the configuration of the natural product to be established as 3aS,8aR.