4-Chlorhomocuban | 35589-16-3

• 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-Chlorhomocuban
• 英文别名: 4-Chloropentacyclo[4.3.0.02,5.03,8.04,7]nonane
• CAS: 35589-16-3
• 化学式: C₉H₉Cl
• 分子量: 152.623
• InChiKey: WBCYVNDSPMRLOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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-Chlorhomocuban 在 silver tetrafluoroborate 、 sodium 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 24.0h， 生成 五环[4.3.0.0(2,4).0(3,8).0(5,7)]壬烷
  参考文献：
  名称：

  Osawa, Eiji; Schneider, Ingrid; Toyne, Kennet J., Chemische Berichte, 1986, vol. 119, # 7, p. 2350 - 2361

  摘要：

  DOI：
• 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 一氟三氯甲烷 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-Chlorhomocuban
  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

文献信息

• Giese, Bernd; Stellmach, Joachim, Chemische Berichte, 1980, vol. 113, # 10, p. 3294 - 3302
  作者：Giese, Bernd、Stellmach, Joachim

  DOI：——

  日期：——
• Toward an understanding of the cubyl and related caged carbocations
  作者：Ernest W. Della、Nicholas J. Head、Wit K. Janowski、Carl H. Schiesser

  DOI：10.1021/jo00079a037

  日期：1993.12

  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.
• Osawa, Eiji; Schneider, Ingrid; Toyne, Kennet J., Chemische Berichte, 1986, vol. 119, # 7, p. 2350 - 2361
  作者：Osawa, Eiji、Schneider, Ingrid、Toyne, Kennet J.、Musso, Hans

  DOI：——

  日期：——