(+)-11β-hydroxy-apoaromadendrone | 99147-42-9

• 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: (+)-11β-hydroxy-apoaromadendrone
• CAS: 99147-42-9
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: WGGGLYPWFRDVEK-BVPDVSAISA-N

物化性质

• 沸点：
  327.4±25.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16.0
• 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：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+)-11β-hydroxy-apoaromadendrone 在 硫酸 、 碘 、 magnesium 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 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
• 作为产物：
  描述：

  1H-Cycloprop[e]azulene, decahydro-1,1,7-trimethyl-4-methylene- 在 臭氧 、 亚磷酸三乙酯 作用下， 反应 6.0h， 生成 (+)-11β-hydroxy-apoaromadendrone
  参考文献：
  名称：

  First preparation of (+)-spathulenol. Regio- and stereoselective oxidation of (+)-aromadendrene with ozone.

  摘要：

  DOI：

  10.1016/s0040-4039(00)94792-0

文献信息

• The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III
  作者：Harrie J.M. Gijsen、Joannes B.P.A. Wijnberg、Gerrit A. Stork、Aede de Groot、Maarten A. de Waard、Johannes G.M. van Nistelrooy

  DOI：10.1016/s0040-4020(01)88765-2

  日期：1992.3

  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.
• First preparation of (+)-spathulenol. Regio- and stereoselective oxidation of (+)-aromadendrene with ozone.
  作者：F.P. van Lier、T.G.M. Hesp、L.M. van der Linde、A.J.A. van der Weerdt

  DOI：10.1016/s0040-4039(00)94792-0

  日期：——