1-methyl-4-((4-methylene-3-propylcyclohex-1-en-1-yl)methyl)bicyclo[2.2.1]heptane | 131236-52-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-methyl-4-((4-methylene-3-propylcyclohex-1-en-1-yl)methyl)bicyclo[2.2.1]heptane
• CAS: 131236-52-7
• 化学式: C₁₉H₃₀
• 分子量: 258.447
• InChiKey: QRQWCAZQXSXHBH-UHFFFAOYSA-N

物化性质

• 沸点：
  334.9±17.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  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

文献信息

• Dianions of 1,4-bis(methylene)cyclohexane. Conformational effects in cyclic and acyclic dilithiated hydrocarbons
  作者：Stephanie D. Meyer、Nancy S. Mills、Joy B. Runnels、Barbara De la Torre、C. Channing Ruud、David K. Johnson

  DOI：10.1021/jo00003a010

  日期：1991.2

  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.