methyl 1,3-diphenyl-2-endo-bicyclo[1.1.0]butanecarboxylate | 1153-33-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl 1,3-diphenyl-2-endo-bicyclo[1.1.0]butanecarboxylate
• 英文别名: methyl 1,3-diphenylbicyclobutane-2-endo-carboxylate
• CAS: 1153-33-9
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: LNDNMPCHOKLLNY-XGWQRUHWSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  351.7±11.0 °C(predicted)
• 密度：
  1.273±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  methyl 1,3-diphenyl-2-endo-bicyclo[1.1.0]butanecarboxylate 以 正辛烷 为溶剂， 反应 0.5h， 生成 methyl 1,3-diphenyl-2-exo-bicyclo[1.1.0]butanecarboxylate
  参考文献：
  名称：

  Methyl 1,3-Diphenylbicyclo[1.1.0]butane-2-exo-carboxylate. new example of the thermal inversion of bicyclobutane system

  摘要：

  A fact of a reversible thermal inversion of exo- and endo-isomers of methyl 1,3-diphenylbicyclo[1.1.0] butane-2-carboxylate was established experimentally. The equilibrium constant of the process at 126A degrees C is 14.2 with endo-isomer prevailing. Using DFT/PBE/L22 method the geometry of the isomers was optimized and also the geometry of the previously studied related exo,exo- and endo,endo-isomers of dimethyl 1,3-diphenylbicyclo[1.1.0] butane-2,4-dicarboxylate. The energy barrier of these mutual conversions was estimated.

  DOI：

  10.1134/s1070428012080027
• 作为产物：
  描述：

  methyl 1,3-diphenyl-2-exo-bicyclo[1.1.0]butanecarboxylate 以 正辛烷 为溶剂， 反应 0.5h， 生成 methyl 1,3-diphenyl-2-endo-bicyclo[1.1.0]butanecarboxylate
  参考文献：
  名称：

  Methyl 1,3-Diphenylbicyclo[1.1.0]butane-2-exo-carboxylate. new example of the thermal inversion of bicyclobutane system

  摘要：

  A fact of a reversible thermal inversion of exo- and endo-isomers of methyl 1,3-diphenylbicyclo[1.1.0] butane-2-carboxylate was established experimentally. The equilibrium constant of the process at 126A degrees C is 14.2 with endo-isomer prevailing. Using DFT/PBE/L22 method the geometry of the isomers was optimized and also the geometry of the previously studied related exo,exo- and endo,endo-isomers of dimethyl 1,3-diphenylbicyclo[1.1.0] butane-2,4-dicarboxylate. The energy barrier of these mutual conversions was estimated.

  DOI：

  10.1134/s1070428012080027