dichloro-(2-chloro-1-cyclohexanyl)methane | 138826-01-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: dichloro-(2-chloro-1-cyclohexanyl)methane
• 英文别名: 1-chloro-2-(dichloromethyl)cyclohexene
• CAS: 138826-01-4
• 化学式: C₇H₉Cl₃
• 分子量: 199.507
• InChiKey: GBJWHKIUHOOGDH-UHFFFAOYSA-N

物化性质

• 沸点：
  214.4±40.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  dichloro-(2-chloro-1-cyclohexanyl)methane 、 异丁烯 在 potassium tert-butylate 作用下， 以 苯 为溶剂， 以18%的产率得到1-chloro-1-(2-chloro-1-cyclohexenyl)-2,2-dimethylcyclopropane
  参考文献：
  名称：

  (2-Chlorovinyl)chlorocarbenes: Generation and reactions with alkenes

  摘要：

  The treatment of Z-1,1,3-trichloro-4,4-dimethyl-2-pentene (Ia) with t-C4H9OK in boiling hexane or benzene gave rise to (Z-2-chloro-3,3-dimethyl-1-butenyl)chlorocarbene (IVa), which reacted with alkenes to give the cyclopropane derivatives (V) in 44-57% yields. Dichloro-(2-chloro-1-alkenyl)methanes (Ib-d), which have a hydrogen atom at the C3 position of the alkenyl substituent, were also used as carbene precursors under these conditions. These compounds gave rise to mixtures of the cyclopropanes (VI)-(VIII) (obtained in up to 57% yields) and the dienes (IX)-(XI) (yields up to 54%). The reaction of cis-2-butene with (2-chloro-1-cyclopentenyl)chlorocarbene (IVd) was found to be completely stereospecific, indicating that this carbene exists in a singlet ground state.

  DOI：

  10.1007/bf00961043
• 作为产物：
  描述：

  2-氯-1-甲酰基-1-环己烯 在 吡啶 、 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以66%的产率得到dichloro-(2-chloro-1-cyclohexanyl)methane
  参考文献：
  名称：

  (2-Chlorovinyl)chlorocarbenes: Generation and reactions with alkenes

  摘要：

  The treatment of Z-1,1,3-trichloro-4,4-dimethyl-2-pentene (Ia) with t-C4H9OK in boiling hexane or benzene gave rise to (Z-2-chloro-3,3-dimethyl-1-butenyl)chlorocarbene (IVa), which reacted with alkenes to give the cyclopropane derivatives (V) in 44-57% yields. Dichloro-(2-chloro-1-alkenyl)methanes (Ib-d), which have a hydrogen atom at the C3 position of the alkenyl substituent, were also used as carbene precursors under these conditions. These compounds gave rise to mixtures of the cyclopropanes (VI)-(VIII) (obtained in up to 57% yields) and the dienes (IX)-(XI) (yields up to 54%). The reaction of cis-2-butene with (2-chloro-1-cyclopentenyl)chlorocarbene (IVd) was found to be completely stereospecific, indicating that this carbene exists in a singlet ground state.

  DOI：

  10.1007/bf00961043