(-)-allospathulenol | 99147-40-7

• 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: (-)-allospathulenol
• 英文别名: spathulenol；(1aR,4aS,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
• CAS: 99147-40-7
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: FRMCCTDTYSRUBE-HVNMYJMUSA-N

物化性质

• 沸点：
  297.0±19.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-allospathulenol 在 Oxone 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 碳酸氢钠 、 丙酮 作用下， 生成 alloaromadendrane-4β, 10α-diol 、 (+)-alloaromadendrane-4α,10β-diol
  参考文献：
  名称：

  The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III

  摘要：

  The monoalcohols (-)-globulol (2), (-)-epiglobulol (3), (-)-ledol (4), and (+)-viridiflorol (5) were synthesized from (+)-aromadendrene (1). The cis-fused alloaromadendrone (14), the key intermediate used in the synthesis of 4 and 5, was obtained from the trans-fused apoaromadendrone (13) via a selective protonation of the thermodynamic enol trimethylsilylether 15. After hydroxylation of the tertiary C11 of 13 with RuO4, (+)-spathulenol (6), (-)-allospathulenol (7), and the aromadendrane diols 8-11 could be prepared. Compounds 2-11 were tested for antifungal properties, but their activity was only moderate.

  DOI：

  10.1016/s0040-4020(01)88765-2
• 作为产物：
  描述：

  (+)-11β-hydroxy-alloaromadendrone 在 吡啶 、 硫酸 、 碘 、 magnesium 作用下， 反应 0.5h， 生成 (-)-allospathulenol
  参考文献：
  名称：

  The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III

  摘要：

  The monoalcohols (-)-globulol (2), (-)-epiglobulol (3), (-)-ledol (4), and (+)-viridiflorol (5) were synthesized from (+)-aromadendrene (1). The cis-fused alloaromadendrone (14), the key intermediate used in the synthesis of 4 and 5, was obtained from the trans-fused apoaromadendrone (13) via a selective protonation of the thermodynamic enol trimethylsilylether 15. After hydroxylation of the tertiary C11 of 13 with RuO4, (+)-spathulenol (6), (-)-allospathulenol (7), and the aromadendrane diols 8-11 could be prepared. Compounds 2-11 were tested for antifungal properties, but their activity was only moderate.

  DOI：

  10.1016/s0040-4020(01)88765-2