trimethyl(((1aR,7R,7aS,7bR)-1,1,7-trimethyl-1a,2,3,5,6,7,7a,7b-octahydro-1H-cyclopropa[e]azulen-4-yl)oxy)silane | 141564-33-2

• 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: trimethyl(((1aR,7R,7aS,7bR)-1,1,7-trimethyl-1a,2,3,5,6,7,7a,7b-octahydro-1H-cyclopropa[e]azulen-4-yl)oxy)silane
• CAS: 141564-33-2
• 化学式: C₁₇H₃₀OSi
• 分子量: 278.51
• InChiKey: SBEYXWFVBNJIPC-UIBBOPPKSA-N

物化性质

• 沸点：
  278.3±8.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trimethyl(((1aR,7R,7aS,7bR)-1,1,7-trimethyl-1a,2,3,5,6,7,7a,7b-octahydro-1H-cyclopropa[e]azulen-4-yl)oxy)silane 在 Oxone 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 碳酸氢钠 、 三乙胺 、 丙酮 作用下， 以 甲醇 为溶剂， 反应 23.0h， 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：

  三甲基氯硅烷 、 α-apo-Aromadendron 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以85%的产率得到trimethyl(((1aR,7R,7aS,7bR)-1,1,7-trimethyl-1a,2,3,5,6,7,7a,7b-octahydro-1H-cyclopropa[e]azulen-4-yl)oxy)silane
  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

文献信息

• Rearrangement reactions of aromadendrane derivatives. The synthesis of (+)-maaliol, starting from natural (+)-aromadendrene-IV
  作者：Harrie J.M. Gijsen、Joannes B.P.A. Wijnberg、Connie van Ravenswaay、Aede de Groot

  DOI：10.1016/s0040-4020(01)85012-2

  日期：1994.4

  Starting from the hydroazulene alpha-ketol 6, which can easily be prepared from (+)-aromadendrene (1), two different routes to hydronaphthalene compounds with a maaliane skeleton have been developed, both proceeding in high overall yield. The first route leads to cis-fused maaliane derivatives; the second one offers access to trans-fused maaliane sesquiterpenes, as demonstrated in this paper in the synthesis of (+)-maaliol (5).