α-apo-Aromadendron | 6790-66-5

• 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: α-apo-Aromadendron
• 英文别名: α-Apoaromadendron；4-Epiapoaromadendron；(+)-apoaromadendrone；(+)-Apoaromadendron；Apoaromadendrene；(-)-alloaromadendrone
• CAS: 6790-66-5；14682-45-2；14917-87-4；95977-69-8；97275-30-4；97950-12-4；99147-41-8
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: YGUOKAXDKNRZMO-VIJOUGIQSA-N

物化性质

• 熔点：
  83 °C
• 沸点：
  285.5±8.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  α-apo-Aromadendron 在 Oxone 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 碳酸氢钠 、 丙酮 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 (+)-viridiflorol
  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：

  α-apo-Aromadendron 在 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 α-apo-Aromadendron
  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