cis-Tricyclo<7.5.0.0^2,8>tetradeca-7,9-diene | 134967-85-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: cis-Tricyclo<7.5.0.0^2,8>tetradeca-7,9-diene
• 英文别名: (8R,9S)-tricyclo[7.5.0.02,8]tetradeca-1(14),2-diene
• CAS: 134967-85-4
• 化学式: C₁₄H₂₀
• 分子量: 188.313
• InChiKey: IHHLJMYHJSFRHI-MQMHXKEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  trans-Tricyclo<7.5.0.0^2,8>tetradeca-7,9-diene 生成 cis-Tricyclo<7.5.0.0^2,8>tetradeca-7,9-diene
  参考文献：
  名称：

  Rearrangements of 1-cyclohexenylmethylenes and their relevance to the mechanism of the phenylcarbene rearrangement

  摘要：

  Gas-phase pyrolysis of 1-cyclohexenyldiazomethane (17) and (2-methyl-1-cyclohexenyl)diazomethane (36) leads to the generation of cyclohexenylmethylenes, 13 and 27, respectively, whose intramolecular rearrangement mechanisms can be inferred from the stable end products. These substituted vinylmethylenes undergo intramolecular pi-addition, but apparently do not participate in an all-carbon Wolff rearrangement. The relevance of these results to the mechanism of the phenylcarbene rearrangement is discussed, and it is suggested that a pi-route with a bicycloheptatriene-like transition state may operate. An attempt to generate 1,3-cyclohexadienylmethylene is described.

  DOI：

  10.1021/jo00017a021

文献信息

• Rearrangements of 1-cyclohexenylmethylenes and their relevance to the mechanism of the phenylcarbene rearrangement
  作者：Paula C. Miller、Peter P. Gaspar

  DOI：10.1021/jo00017a021

  日期：1991.8

  Gas-phase pyrolysis of 1-cyclohexenyldiazomethane (17) and (2-methyl-1-cyclohexenyl)diazomethane (36) leads to the generation of cyclohexenylmethylenes, 13 and 27, respectively, whose intramolecular rearrangement mechanisms can be inferred from the stable end products. These substituted vinylmethylenes undergo intramolecular pi-addition, but apparently do not participate in an all-carbon Wolff rearrangement. The relevance of these results to the mechanism of the phenylcarbene rearrangement is discussed, and it is suggested that a pi-route with a bicycloheptatriene-like transition state may operate. An attempt to generate 1,3-cyclohexadienylmethylene is described.