Variculanol 17-<(S)-O-methylmandelate> | 135513-24-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Variculanol 17-<(S)-O-methylmandelate>
• 英文别名: Variculanol 17-((S)-O-methylmandelate)
• CAS: 135513-24-5；135559-65-8
• 化学式: C₃₄H₄₈O₄
• 分子量: 520.753
• InChiKey: IGWJZWRDNIRARQ-LZQMGZNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (S)-(+)-alpha-甲氧基苯乙酸 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.17h， 生成 Variculanol 17-<(S)-O-methylmandelate>
  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