5-chloro-2,6,6-trimethyl-3-(dimethylmethylene)-1,4-heptadiene | 138826-09-2

• 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: 5-chloro-2,6,6-trimethyl-3-(dimethylmethylene)-1,4-heptadiene
• 英文别名: (4Z)-5-chloro-2,6,6-trimethyl-3-propan-2-ylidenehepta-1,4-diene
• CAS: 138826-09-2
• 化学式: C₁₃H₂₁Cl
• 分子量: 212.763
• InChiKey: ZNHAQDRHOAOFJA-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  Z-1,1,3-trichloro-4,4-dimethyl-2-pentene 在 potassium tert-butylate 作用下， 以 氘代苯 、 苯 为溶剂， 反应 10.0h， 生成 5-chloro-2,6,6-trimethyl-3-(dimethylmethylene)-1,4-heptadiene
  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

文献信息

• (2-Chlorovinyl)chlorocarbenes: Generation and reactions with alkenes
  作者：K. N. Shavrin、G. P. Okonnishnikova、O. M. Nefedov

  DOI：10.1007/bf00961043

  日期：1991.11

  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.