(1R,2S,5R,6S)-9-benzhydrylidene-7,8-dioxatricyclo[4.2.1.02,5]non-3-ene | 132465-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,5R,6S)-9-benzhydrylidene-7,8-dioxatricyclo[4.2.1.02,5]non-3-ene
• CAS: 132465-27-1
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: FUIWSUVUTIUYFY-OBMJPTGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Benzhydrylidenetetracyclo-<3.2.0.0^2,7.0^4,6>heptane 在 氧气 作用下， 以 正己烷 为溶剂， 反应 0.33h， 以4%的产率得到(1R,2S,5R,6S)-9-benzhydrylidene-7,8-dioxatricyclo[4.2.1.02,5]non-3-ene
  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

文献信息

• Novel photoreactions of benzhydrylidenequadricyclane and quadricyclanone: a new route to trimethylenemethane and oxyallyl derivatives
  作者：Takashi Hirano、Tsutomu Kumagai、Tsutomu Miyashi、Kimio Akiyama、Yusaku Ikegami

  DOI：10.1021/jo00005a044

  日期：1991.3

  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.