4-isopropylidene-1-cyclohexene | 119182-77-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 4-isopropylidene-1-cyclohexene
• 英文别名: 4-isopropylidene-cyclohexene；4-Isopropyliden-cyclohexen；3-Isopropylidencyclohexen；4-Propan-2-ylidenecyclohexene
• CAS: 119182-77-3
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: VJKVZVQAJMNQFY-UHFFFAOYSA-N

物化性质

• 沸点：
  163.1±15.0 °C(Predicted)
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-isopropylidene-1-cyclohexene 、 alkaline earth salt of/the/ methylsulfuric acid 生成 异丙苯
  参考文献：
  名称：

  Sopow, Zhurnal Obshchei Khimii, 1955, vol. 25, p. 2082,2087; engl. Ausg. S. 2035, 2040

  摘要：

  DOI：
• 作为产物：
  描述：

  3-环己烯-1-羧酸甲酯 以 二甲基亚砜 为溶剂， 生成 4-isopropylidene-1-cyclohexene
  参考文献：
  名称：

  Molecules with twist bent bonds. The synthesis, properties, and reactions of trans-bicyclo[4.1.0]hept-3-ene and certain methylated derivatives

  摘要：

  DOI：

  10.1021/ja00189a046

文献信息

• Molecules with Twist Bent Bonds. A Comparison of the Thermal and Transition-Metal-Complex Promoted Rearrangements of st]Derivatives of trans-Bicyclo[4.1.0]hept-3-ene
  作者：Paul G. Gassman、Kata Mlinarić-Majerski

  DOI：10.1016/s0040-4039(00)80613-9

  日期：1988.1

  7-Methyl-trans-bicyclo[4.1.0]hept-3-ene has been synthesized and the thermal and transition-metal-complex promoted rearrangements of trans-bicyclo[4.1.0]hept-3-ene, 7-methyl-trans-bicyclo[4.1.0]hept-3-ene, and 7,7-dimethyl-trans-bicyclo[4.1.0]hept-3-ene have been compared.

  已经合成了7-甲基-反-双环[4.1.0]庚-3-烯，并且热和过渡金属络合物促进了反-双环[4.1.0]庚-3-烯7-甲基-的重排。比较了反式-双环[4.1.0]庚-3-烯和7,7-二甲基-反式-双环[4.1.0]庚-3-烯。
• Petrow; Sopow, Zhurnal Obshchei Khimii, 1952, vol. 22, p. 591,595, 599; engl. Ausg. S. 653, 655, 659
  作者：Petrow、Sopow

  DOI：——

  日期：——
• The Interaction of π Orbitals with a Carbocation over Three σ Bonds
  作者：Joseph B. Lambert、Sol M. Ciro

  DOI：10.1021/jo951643d

  日期：1996.1.1

  The semi-pi analogue of double hyperconjugation (''hyperconjugation/conjugation'') has been examined in 4-isopropylidenecyclohexyl mesylate (4-OMs) by comparison with the saturated analogue, trans-4-isopropylcyclohexyl mesylate(5-OMs). The unsaturated substrate reacts in 97% trifluoroethanol only four times faster than the saturated substrate. Raber-Harris plots indicate that both substrates react by k(s) mechanisms; i.e., solvolysis occurs with solvent assistance rather than carbocation formation. These results are consistent with the absence of a direct, through-bond interaction of the double bond with the reactive center. The absence is caused at least in part by less than ideal overlap of the gamma, delta pi orbitals with the alpha,beta sigma orbitals. In contrast, an electron-rich tin atom attached to the 4-position provides a large rate enhancement and changes the mechanism to carbocation formation through double hyperconjugation.
• GASSMAN, PAUL G.;MLINARIC-MAJERSKI, KATA, TETRAHEDRON LETT., 29,(1988) N 38, C. 4803-4806
  作者：GASSMAN, PAUL G.、MLINARIC-MAJERSKI, KATA

  DOI：——

  日期：——