1-Methyl-4-methylidene-3-propylcyclohexene | 131236-45-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1-Methyl-4-methylidene-3-propylcyclohexene
• 英文别名: 1-methyl-4-methylidene-3-propylcyclohexene
• CAS: 131236-45-8
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: BOCYDEYHWOYLKW-UHFFFAOYSA-N

物化性质

• 沸点：
  198.7±15.0 °C(Predicted)
• 密度：
  0.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  1-氯丙烷 、 1,4-二亚甲基环己烷 在 正丁基锂 、 四甲基乙二胺 作用下， 反应 216.0h， 以11%的产率得到对二甲苯
  参考文献：
  名称：

  Dianions of 1,4-bis(methylene)cyclohexane. Conformational effects in cyclic and acyclic dilithiated hydrocarbons

  摘要：

  Dimetalation of 1,4-bis(methylene)cyclohexane results in formation of the p-xylene dianion via the linearly conjugated dianion 4. In contrast, 2-methyl-1,5-hexadiene, an acyclic analogue of 1,4-bis(methylene)cyclohexane, undergoes isomerization via the linearly conjugated dianion 12, rather than hydride elimination. MNDO calculations of the conformations of dilithiated 4 and 12 show that 4 is effectively planar, with a symmetrical distribution of charge. Dilithiated 12 is nonplanar, with an almost right angle bend in the pi-system. The dianion can therefore be considered as two allyl anions which are orthogonal to each other. The difference in calculated conformations of 4 and 12 is advanced as the reason for the different reactivity of the two systems.

  DOI：

  10.1021/jo00003a010