Variculanol | 135513-21-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Variculanol
• 英文别名: (1R,2E,5S,6R,7R,9S,10R,11E,15R)-2,9,12-trimethyl-16-methylidene-6-propan-2-yltricyclo[13.3.0.05,9]octadeca-2,11-diene-7,10-diol
• CAS: 135513-21-2
• 化学式: C₂₅H₄₀O₂
• 分子量: 372.591
• InChiKey: OHABHHQPUHXDEY-CRJDLSTQSA-N

物化性质

• 沸点：
  492.6±45.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)
• 溶解度：
  二氯甲烷：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Variculanol 在 吡啶 作用下， 以3.0 mg的产率得到Variculanol 1,17-diacetate
  参考文献：
  名称：

  Variculanol: structure and absolute stereochemistry of a novel 5/12/5 tricyclic sesterterpenoid from Aspergillus variecolor

  摘要：

  The structure, absolute stereochemistry, and conformation of variculanol, a sesterterpenoid with novel skeleton isolated from Aspergillus variecolor, has been described. The molecular structure was deduced from extensive application of 2D NMR methods, in particular HMBC, which established the unambiguous assignment of the novel 5/12/5 ring system. NOEDS measurements were very useful in establishing the relative stereochemistry. The NMR-mandelate method and CD spectral analysis of the 1,17-bis(4-bromobenzoate) were used to determine the absolute stereochemistry. A unique solution-phase conformation was determined from both extensive NOE measurements and MM2 calculations and optimization.

  DOI：

  10.1021/jo00019a030