cis-3-tert-butyl-bicyclo<3.3.0>oct-2-ene | 137039-77-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: cis-3-tert-butyl-bicyclo<3.3.0>oct-2-ene
• 英文别名: cis-3-tert-butyl-bicyclo[3.3.0]oct-2-ene；(3aS,6aS)-5-tert-butyl-1,2,3,3a,4,6a-hexahydropentalene
• CAS: 137039-77-1
• 化学式: C₁₂H₂₀
• 分子量: 164.291
• InChiKey: HANFDEKNRGCNBH-ZJUUUORDSA-N

物化性质

• 沸点：
  210.3±7.0 °C(predicted)
• 密度：
  0.910±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• 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：

  3-tert-butyl-2-cycloocten-1-one 在 sodium methylate 作用下， 以 苯 为溶剂， 反应 14.0h， 生成 cis-3-tert-butyl-bicyclo<3.3.0>oct-2-ene
  参考文献：
  名称：

  Cumulene photochemistry: photoreactions of a strained 1,2-cyclooctadiene

  摘要：

  The singlet and triplet photoreactions of 1-tert-butyl-1,2-cyclooctadiene (1) are described. This is the first example of an isolable eight-membered ring allene and is predicted to have a bent allenic unit. Triplet reactions of 1 are phase dependent. Benzene-sensitized irradiation affords products of hydrogen abstraction at tert-butyl or ring carbons in vapor phase or solution phase, respectively. Direct irradiation of thoroughly degassed pentane solutions at 254 nm affords primarily 3-tert-butylbicyclo[3.3.0]oct-2-ene and other products that are attributed to initial excited-state 1,2-hydrogen migration to a vinylcarbene. Independent generation of this vinylcarbene gives a similar collection of products, which include an isolable bicyclo[5.1.0]oct-1(8)-ene. Irradiation of 1 in oxygenated solutions yields tert-butylcycloheptene (15), apparently through loss of carbon monoxide from an intermediate cyclopropanone. Oxidation of 1 with m-CPBA also leads efficiently to 15.

  DOI：

  10.1021/jo00022a029