(1S,2S,5R)-2-methoxybicyclo[3.2.0]hept-6-en-3-one | 132465-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,5R)-2-methoxybicyclo[3.2.0]hept-6-en-3-one
• CAS: 132465-34-0；132561-87-6
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: OCFRPERTFFMTKN-HAFWLYHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 3-Benzhydrylidenetetracyclo-<3.2.0.0^2,7.0^4,6>heptane 反应 6.0h， 以14%的产率得到(1S,2S,5R)-2-methoxybicyclo[3.2.0]hept-6-en-3-one
  参考文献：
  名称：

  Novel photoreactions of benzhydrylidenequadricyclane and quadricyclanone: a new route to trimethylenemethane and oxyallyl derivatives

  摘要：

  The irradiation of 3-benzhydrylidenequadricyclane (1) generated a trimethylenemethane (TMM) derivative, 3-benzhydrylidenebicyclo[3.2.0]hept-6-ene-2,4-diyl (3), which dimerized and could be chemically captured by molecular oxygen and acrylonitrile, but not by furan, methanol, or ethyl vinyl ether. The triplet nature of 3 was confirmed by EPR, emission, and absorption spectra. By contrast, the irradiation of quadricyclanone (2) generated the singlet oxyallyl (OA), 3-oxobicyclo[3.2.0]hept-6-ene-2,4-diyl (4) which could be captured by furan, methanol, and ethyl vinyl ether, but not by molecular oxygen or acrylonitrile, indicating the zwitterionic and electron-accepting nature of 4.

  DOI：

  10.1021/jo00005a044