9-Chloro-1,4,5,8-tetrahydro-4a,8a-methanonaphthalene | 18963-51-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 9-Chloro-1,4,5,8-tetrahydro-4a,8a-methanonaphthalene
• 英文别名: 9,10-Chlormethylen-1,4,5,8,9,10-hexahydro-naphthalin；11-Chlorotricyclo[4.4.1.01,6]undeca-3,8-diene
• CAS: 18963-51-4
• 化学式: C₁₁H₁₃Cl
• 分子量: 180.677
• InChiKey: NMPVWBVZOGFPKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  9-Chloro-1,4,5,8-tetrahydro-4a,8a-methanonaphthalene 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， 反应 44.0h， 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 、 锌 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以92%的产率得到9-Chloro-1,4,5,8-tetrahydro-4a,8a-methanonaphthalene
  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

文献信息

• Angular substituents via cyclopropane derivatives of .beta.,.gamma.-unsaturated ketones
  作者：James J. Sims、V. K. Honwad

  DOI：10.1021/jo01255a004

  日期：1969.3