1-Homocubanol | 172978-45-9

• 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: 1-Homocubanol
• 英文别名: Pentacyclo[4.3.0.02,5.03,8.04,7]nonan-1-ol
• CAS: 172978-45-9
• 化学式: C₉H₁₀O
• 分子量: 134.178
• InChiKey: LZYDDDGJWWPHLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  261.2±8.0 °C(Predicted)
• 密度：
  1.777±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  三氟甲磺酸酐 、 1-Homocubanol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到1-Homocubyl triflate
  参考文献：
  名称：

  Bridgehead Carbocations: Correlation Between MP2/6-31G* Cation Energies of Some Caged Cations and the Solvolysis Rates of Their Precursor Triflates

  摘要：

  Synthesis of the series of caged systems, 4-homocubyl triflate (7), 1-homocubyl triflate (10), 6-tricyclo[3.1.1.0(3,6)]heptyl (norcubyl) triflate (11), and 6-tricyclo[3.2.1.0(3,6)]octyl triflate (12) together with 1-norbornyl triflate (9) is described. Examination of their behavior under solvolysis conditions in 80% ethanol shows that in each case ionization occurs to give the corresponding bridgehead cation and that there is an enormous difference in reactivity between the triflates. A linear correlation is observed when the logarithm of the ionization rates of the triflates 7 and 9-12 as well as that of cubyl trinate (8) are plotted against the MP2-derived energies of the corresponding bridgehead cations.

  DOI：

  10.1021/jo00129a015
• 作为产物：
  描述：

  cubylmethanol 在 硫酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.0h， 以92%的产率得到1-Homocubanol
  参考文献：
  名称：

  Bridgehead Carbocations: Correlation Between MP2/6-31G* Cation Energies of Some Caged Cations and the Solvolysis Rates of Their Precursor Triflates

  摘要：

  Synthesis of the series of caged systems, 4-homocubyl triflate (7), 1-homocubyl triflate (10), 6-tricyclo[3.1.1.0(3,6)]heptyl (norcubyl) triflate (11), and 6-tricyclo[3.2.1.0(3,6)]octyl triflate (12) together with 1-norbornyl triflate (9) is described. Examination of their behavior under solvolysis conditions in 80% ethanol shows that in each case ionization occurs to give the corresponding bridgehead cation and that there is an enormous difference in reactivity between the triflates. A linear correlation is observed when the logarithm of the ionization rates of the triflates 7 and 9-12 as well as that of cubyl trinate (8) are plotted against the MP2-derived energies of the corresponding bridgehead cations.

  DOI：

  10.1021/jo00129a015