4-Iodopentacyclo<4.3.0.0^2,5.0^3,8.0^4,7>nonane | 153002-04-1

• 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-Iodopentacyclo<4.3.0.0^2,5.0^3,8.0^4,7>nonane
• 英文别名: 4-Iodohomocubane；4-Iodopentacyclo[4.3.0.02,5.03,8.04,7]nonane
• CAS: 153002-04-1
• 化学式: C₉H₉I
• 分子量: 244.075
• InChiKey: CLZXYPVISNBJHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  五环[4.3.0.0~2,5~.0~3,8~.0~4,7~]壬烷-4-羧酸 在 lead(IV) acetate 、 碘 作用下， 以90%的产率得到4-Iodopentacyclo<4.3.0.0^2,5.0^3,8.0^4,7>nonane
  参考文献：
  名称：

  Toward an understanding of the cubyl and related caged carbocations

  摘要：

  The product ratios observed upon fluorodeiodination of a series of caged cyclobutane-containing iodides are explained on the basis of the relative energies of the intermediate cations involved. The relative energies of these cations have been evaluated by ab initio calculations with the inclusion of electron correlation (MP2/6-31G*//RHF/3-21G; MP2/6-31G**), the results of which lend support to the view that hyperconjugative involvement of the cationic center with the alpha,beta and beta,gamma C-C bonds in each cyclobutyl moiety is the critical factor responsible for the stability of the cation in each case. The degree of stabilization of the cations is a reflection of the number and relative importance of several resonance contributors (corresponding to the involvement of the carbon sigma-framework) to their overall structure and is strongly dependent on the geometry of the rigid carbon framework in each case.

  DOI：

  10.1021/jo00079a037