5-(1-甲基乙基)环己-1,3-二烯 | 35776-64-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 5-(1-甲基乙基)环己-1,3-二烯
• 英文名称: 5-Isopropyl-cyclohexa-1,3-dien
• 英文别名: 5-(1-Methylethyl)-1,3-cyclohexadiene；5-propan-2-ylcyclohexa-1,3-diene
• CAS: 35776-64-8
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: VXIBOZDOTNVUEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  30-31 °C(Press: 4 Torr)
• 密度：
  0.8531 g/cm3(Temp: 15 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  9
• 可旋转键数：
  1
• 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：

  5-(1-甲基乙基)环己-1,3-二烯 生成 异丙基环己烷
  参考文献：
  名称：

  Treibs, Chemische Berichte, 1933, vol. 66, p. 610,618

  摘要：

  DOI：
• 作为产物：
  描述：

  Thiocarbonic acid O-((1R,6R)-6-isopropyl-cyclohex-3-enyl) ester O-phenyl ester 以50%的产率得到5-(1-甲基乙基)环己-1,3-二烯
  参考文献：
  名称：

  Unusual Facial Selectivity in the Cycloaddition of Singlet Oxygen to a Simple Cyclic Diene¹

  摘要：

  Syntheses of 5-isopropyl-1,3-cyclohexadiene and syn-5-isopropyl-2,3-dioxabicyclo[2.2.2]octane, by routes that would allow completely diastereoselective introduction of deuterium labels, are described. The reaction of the isopropyl cyclohexadiene with singlet oxygen is shown to give an endoperoxide that is derived by preferential attack on the more sterically hindered face of the diene, A possible mechanistic explanation of this result is that the attack from the less hindered face leads to ''ene'' reaction rather than endoperoxide formation, However, this mechanism would require that the ''ene'' reaction and cycloaddition proceed via a common intermediate-presumably a perepoxide.

  DOI：

  10.1021/jo9604292

文献信息

• Primary deuterium kinetic isotope effects for the thermal [1,7] sigmatropic rearrangement of 7-methylocta-1,3(Z),5(Z)-triene
  作者：John E. Baldwin、V. Prakash. Reddy

  DOI：10.1021/ja00232a040

  日期：1988.11

  6(Z)-triene over the temperature range 60-115degree}C through a first-order process characterized kinetically by the activation parameters log Asup H} = 9.8 and Esub a}sup H} = 21.5 kcal/mol. Parallel kinetic work with the 7-deuterio-7-methyloctatriene establishes the Arrhenius parameters log Asup D} = 10.3 and Esub a}sup D} = 23.5 kcal/mol. Thus Asup D}/Asup H} = 3.2 and (Esub a}sup D} - Esub

  7-Methylocta-1,3(Z),5(Z)-triene 在 60-115°C 的温度范围内异构化为 2-methylocta-2,4(Z),6(Z)-triene由活化参数 log Asup H} = 9.8 和 Esub a}sup H} = 21.5 kcal/mol 在动力学上表征的 - 阶过程。与 7-deuterio-7-methyloctatriene 的平行动力学工作建立了 Arrhenius 参数 log Asup D} = 10.3 和 Esub a}sup D} = 23.5 kcal/mol。因此，Asup D}/Asup H} = 3.2 和 (Esub a}sup D} - Esub a}sup H}) = 2.0 kcal/mol，以及（ 1,7) sigmatropic 氢迁移是明显的。25 个参考文献，3 个图，1 个标签。
• A Kinetic Study of the Cyclohexadienyl Radical. I. Disproportionation and Combination with the Isopropyl Radical
  作者：D. G. L. James、R. D. Suart

  DOI：10.1021/ja01078a012

  日期：1964.12
• Treibs, Chemische Berichte, 1933, vol. 66, p. 610,618
  作者：Treibs

  DOI：——

  日期：——
• Unusual Facial Selectivity in the Cycloaddition of Singlet Oxygen to a Simple Cyclic Diene¹
  作者：Kelly M. Davis、Barry K. Carpenter

  DOI：10.1021/jo9604292

  日期：1996.1.1

  Syntheses of 5-isopropyl-1,3-cyclohexadiene and syn-5-isopropyl-2,3-dioxabicyclo[2.2.2]octane, by routes that would allow completely diastereoselective introduction of deuterium labels, are described. The reaction of the isopropyl cyclohexadiene with singlet oxygen is shown to give an endoperoxide that is derived by preferential attack on the more sterically hindered face of the diene, A possible mechanistic explanation of this result is that the attack from the less hindered face leads to ''ene'' reaction rather than endoperoxide formation, However, this mechanism would require that the ''ene'' reaction and cycloaddition proceed via a common intermediate-presumably a perepoxide.