4-Ethoxyhomocubane | 55053-95-7

• 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: 4-Ethoxyhomocubane
• 英文别名: Ethyl pentacyclo[4.3.0.0(2,5).0(3,8).0(4,7)]non-4-YL ether；4-ethoxypentacyclo[4.3.0.02,5.03,8.04,7]nonane
• CAS: 55053-95-7
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: VTEAFGTZEXYUBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-Iodopentacyclo<4.3.0.0^2,5.0^3,8.0^4,7>nonane 在 亚碘酰苯 、 水 、 三乙胺 作用下， 反应 1.0h， 生成 4-Ethoxyhomocubane
  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

文献信息

• Bridgehead Carbocations: Correlation Between MP2/6-31G* Cation Energies of Some Caged Cations and the Solvolysis Rates of Their Precursor Triflates
  作者：Ernest W. Della、Wit K. Janowski

  DOI：10.1021/jo00129a015

  日期：1995.12

  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.