(4aR,6aR,6bS)-6a,6b-dihydrocyclobuta[4,5]cyclopenta[1,2-c][1,2]dioxole-3,3(4aH)-dicarbonitrile | 138062-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (4aR,6aR,6bS)-6a,6b-dihydrocyclobuta[4,5]cyclopenta[1,2-c][1,2]dioxole-3,3(4aH)-dicarbonitrile
• CAS: 138062-59-6；138230-84-9
• 化学式: C₁₀H₆N₂O₂
• 分子量: 186.17
• InChiKey: GOMOLPJMMBURMO-ZKWXMUAHSA-N

物化性质

• 沸点：
  427.7±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.04
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-Methylentetracyclo<3.2.0.0^2,7.0^4,6>heptan-8,8-dicarbonitril 在 氧气 作用下， 以 正己烷 为溶剂， 反应 0.25h， 以3%的产率得到(4aR,6aR,6bS)-6a,6b-dihydrocyclobuta[4,5]cyclopenta[1,2-c][1,2]dioxole-3,3(4aH)-dicarbonitrile
  参考文献：
  名称：

  Inversion of the ground-state spin multiplicity by electron-withdrawing groups in trimethylenemethane derivatives generated photochemically from methylenequadricyclane derivatives

  摘要：

  An inversion of the ground-state spin multiplicity of trimethylenemethane (TMM) by electron-withdrawing groups was investigated by EPR spectroscopy, for a series of TMMs 2b-g generated photochemically from methylenequadricyclanes 1b-g. Curie law analyses between 4 and 50 K proved the triplet ground states of the monophenyl derivative 2b and the monocyano derivatives 2c-d as well as that of the diphenyl derivative 2a. The dicarbomethoxy derivative 2e also exhibited the EPR signal, but the Curie plot was nonlinear and the signal disappeared irreversibly above 10K. The triplet ground state was inverted to the singlet by the carbomethoxy-cyano and dicyano substitutions, and 2f and 2g were EPR silent species similar to the singlet oxyallyl (OA) derivative 2h. The singlet ground state of 2g was demonstrated by its chemical behaviors which resemble those of 2h.

  DOI：

  10.1021/jo00029a018