2-(Prop-2-enylidene)cyclohexanone | 139166-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Prop-2-enylidene)cyclohexanone
• 英文别名: (2E)-2-prop-2-enylidenecyclohexan-1-one
• CAS: 139166-40-8
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: YWPRKDKIBDWWCV-VMPITWQZSA-N

物化性质

• 沸点：
  238.4±10.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(Prop-2-enylidene)cyclohexanone 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 生成 1-Methylene-2-allylidenecyclohexane
  参考文献：
  名称：

  Thermal isomerization of a vinylcyclobutene to a cyclohexadiene

  摘要：

  Above 100-degrees-C 5-methylenespiro[3.5]non-1-ene, 1, undergoes cyclobutene ring opening to (E)-triene 2 and apparent 1,3-shift to a hexahydronaphthalene, 3, in a 3 to 1 ratio. (E)-Triene 2 gives 3 in a competitive reaction. The activation energies for all three processes are obtained from a kinetic simulation at three temperatures. It is likely that the (Z)-triene 4, also derived by cyclobutene ring opening, is an intermediate in the 1 to 3 conversion. Speculation on the 2 to 3 conversion focuses on the possible intermediacy of a 3-vinylcyclohexenocyclobutene, 5. The apparent noninvolvement of a concerted 1,3-shift in the 1 to 3 reaction is discussed.

  DOI：

  10.1021/jo00033a014
• 作为产物：
  描述：

  trans-2-acetoxy-1-cyclohexanol 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-(Prop-2-enylidene)cyclohexanone
  参考文献：
  名称：

  Thermal isomerization of a vinylcyclobutene to a cyclohexadiene

  摘要：

  Above 100-degrees-C 5-methylenespiro[3.5]non-1-ene, 1, undergoes cyclobutene ring opening to (E)-triene 2 and apparent 1,3-shift to a hexahydronaphthalene, 3, in a 3 to 1 ratio. (E)-Triene 2 gives 3 in a competitive reaction. The activation energies for all three processes are obtained from a kinetic simulation at three temperatures. It is likely that the (Z)-triene 4, also derived by cyclobutene ring opening, is an intermediate in the 1 to 3 conversion. Speculation on the 2 to 3 conversion focuses on the possible intermediacy of a 3-vinylcyclohexenocyclobutene, 5. The apparent noninvolvement of a concerted 1,3-shift in the 1 to 3 reaction is discussed.

  DOI：

  10.1021/jo00033a014

文献信息

• Barillier, Daniel; Benhida, Rachid; Vazeux, Michel, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 78, # 1-4, p. 83 - 96
  作者：Barillier, Daniel、Benhida, Rachid、Vazeux, Michel

  DOI：——

  日期：——
• SAHNI S. B.; GUPTA S. M., VISHWAKAYMA, 1978, 19, NO 4, 29-31
  作者：SAHNI S. B.、 GUPTA S. M.

  DOI：——

  日期：——
• Thermal isomerization of a vinylcyclobutene to a cyclohexadiene
  作者：Gitendra C. Paul、Joseph J. Gajewski

  DOI：10.1021/jo00033a014

  日期：1992.3

  Above 100-degrees-C 5-methylenespiro[3.5]non-1-ene, 1, undergoes cyclobutene ring opening to (E)-triene 2 and apparent 1,3-shift to a hexahydronaphthalene, 3, in a 3 to 1 ratio. (E)-Triene 2 gives 3 in a competitive reaction. The activation energies for all three processes are obtained from a kinetic simulation at three temperatures. It is likely that the (Z)-triene 4, also derived by cyclobutene ring opening, is an intermediate in the 1 to 3 conversion. Speculation on the 2 to 3 conversion focuses on the possible intermediacy of a 3-vinylcyclohexenocyclobutene, 5. The apparent noninvolvement of a concerted 1,3-shift in the 1 to 3 reaction is discussed.