tricyclo<5.5.0.0^1.6>dec-3-ene | 135663-42-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: tricyclo<5.5.0.0^1.6>dec-3-ene
• 英文别名: tricyclo[5.5.0.0^1.6]dec-3-ene；tricyclo[5.5.0.01,6]dodec-3-ene
• CAS: 135663-42-2
• 化学式: C₁₂H₁₈
• 分子量: 162.275
• InChiKey: APCKEUGNHWGMJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 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-(trimethylsilyl)-8-chlorobicyclo<5.1.0>octane 在 四丁基氟化铵 作用下， 反应 4.0h， 生成 tricyclo<5.5.0.0^1.6>dec-3-ene
  参考文献：
  名称：

  1,3-Bridged cyclopropenes

  摘要：

  Solid fluoride deposited on glass helices has been used to effect the gas-phase elimination of 1-(trimethylsilyl)-7-chlorobicyclo[4.1.0]heptane and 1-(trimethylsilyl)-8-chlorobicyclo[5.1.0]octane to yield bicyclo[4.1.0]hept-1(7)-ene and bicyclo[5.1.0]oct-1(8)-ene, respectively. Bicyclo[4.1.0]hept-1(7)-ene dimerizes below ca. -90-degrees-C via an ene reaction to yield a new cyclopropene, which then couples to form tetramers. The structures of two tricyclohexane tetramers were determined by X-ray crystallography. The ene dimer was found to react with molecular oxygen to yield two carbonyl compounds identified as 2-(1-bicyclo[4.1.0]heptyl)cyclohexene-1-carboxaldehyde and 3-(1-bicyclo[4.1.0]heptyl)cyclohept-2-en-1-one. These compounds are thought to result from the reaction of molecular oxygen with carbenes that would arise from cyclopropene-vinylcarbene rearrangements. Bicyclo[5.1.0]oct-1(8)-ene is considerably more stable than its lower homologue but also dimerizes via an ene reaction. 7-Chlorobicyclo[4.1.0]hept-1(7)-ene rearranges below -90-degrees-C to yield 2-chloro-1,3-cycloheptadiene.

  DOI：

  10.1021/ja00021a025