(1aα,2aα,6aα,7aα)-8,8-Dichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methanonaphtho<2,3-b>oxirene | 135257-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1aα,2aα,6aα,7aα)-8,8-Dichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methanonaphtho<2,3-b>oxirene
• 英文别名: (1aα,2aα,6aα,7aα)-8,8-Dichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methanonaphtho[2,3-b]oxirene；(1R,3R,5S,7S)-12,12-dichloro-4-oxatetracyclo[5.4.1.01,7.03,5]dodec-9-ene
• CAS: 135257-84-0
• 化学式: C₁₁H₁₂Cl₂O
• 分子量: 231.122
• InChiKey: ZNMPIKYJPNQSHC-YNFQOJQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1aα,2aα,6aα,7aα)-8,8-Dichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methanonaphtho<2,3-b>oxirene 在 氢氧化钾 、 sodium hydroxide 、 aluminium(III) iodide 、 苄基三乙基氯化铵 、 间氯过氧苯甲酸 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 51.0h， 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 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(1aα,2aα,6aα,7aα)-8,8-Dichloro-1a,2,3,6,7,7a-hexahydro-2a,6a-methanonaphtho<2,3-b>oxirene
  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

• .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
  作者：Brian Halton、Sarah G. G. Russell

  DOI：10.1021/jo00019a015

  日期：1991.9

  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.