(1aα,2aα,6aα,7aα)-1,1,8-Trichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methano-1H-cyclopropanaphthalene | 102618-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1aα,2aα,6aα,7aα)-1,1,8-Trichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methano-1H-cyclopropanaphthalene
• 英文别名: (1aα,2aα,6aα,7aα)-1,1,8-Trichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methano-1H-cyclopropa[b]naphthalene
• CAS: 102618-68-8
• 化学式: C₁₂H₁₃Cl₃
• 分子量: 263.594
• InChiKey: QVCRVDYOUKCQTJ-HQUNYVMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (1aα,2aα,6aα,7aα)-1,1,8-Trichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methano-1H-cyclopropanaphthalene 在 sodium hydroxide 、 苄基三乙基氯化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (1aα,2aα,3aα,4aα,5aα,6aα)-1,1,4,4,7-Pentachlorooctahydro-1H,3H-methanodicyclopropanaphthalene
  参考文献：
  名称：

  .pi.-Selective dichlorocyclopropanation and epoxidation of 9-chloro-1,4,5,8-tetrahydro-4a,6a-methanonaphthalene. Controlled synthesis of the C-9 epimers of (1a.alpha.,2a.alpha.,6a.alpha.,7a.alpha.)-1,8,8-trichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methanocyclopropa[b]naphthalene

  摘要：

  Dichlorocarbene addition to the 9-chloromethanonaphthalene 3 shows remarkable pi-selectivity; syn trichloride 5 is the only monoadduct isolated (72%). Epoxidation likewise yields the syn epoxide 6 (78%), which, on dichlorocyclopropanation and deoxygenation, gives the epimeric trichloride 8. The regioselectivities are in accord with PM3-derived molecular electrostatic potentials.

  DOI：

  10.1021/jo00019a015
• 作为产物：
  描述：

  (4aα,8aα)-9,9-dichloro-1,4,5,8-tetrahydro-4a,8a-methanonaphthalene 在 氢氧化钾 、 sodium hydroxide 、 苄基三乙基氯化铵 、 锌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (1aα,2aα,6aα,7aα)-1,1,8-Trichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methano-1H-cyclopropanaphthalene
  参考文献：
  名称：

  .pi.-Selective dichlorocyclopropanation and epoxidation of 9-chloro-1,4,5,8-tetrahydro-4a,6a-methanonaphthalene. Controlled synthesis of the C-9 epimers of (1a.alpha.,2a.alpha.,6a.alpha.,7a.alpha.)-1,8,8-trichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methanocyclopropa[b]naphthalene

  摘要：

  Dichlorocarbene addition to the 9-chloromethanonaphthalene 3 shows remarkable pi-selectivity; syn trichloride 5 is the only monoadduct isolated (72%). Epoxidation likewise yields the syn epoxide 6 (78%), which, on dichlorocyclopropanation and deoxygenation, gives the epimeric trichloride 8. The regioselectivities are in accord with PM3-derived molecular electrostatic potentials.

  DOI：

  10.1021/jo00019a015