10,11-Bis(2-fluorophenyl)-9,12-diphenyltetracyclo[6.4.0.04,12.05,9]dodec-10-ene | 1507349-13-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 10,11-Bis(2-fluorophenyl)-9,12-diphenyltetracyclo[6.4.0.04,12.05,9]dodec-10-ene
• 英文别名: 10,11-bis(2-fluorophenyl)-9,12-diphenyltetracyclo[6.4.0.04,12.05,9]dodec-10-ene
• CAS: 1507349-13-4
• 化学式: C₃₆H₃₀F₂
• 分子量: 500.631
• InChiKey: IJVQAOJZMIFUEE-UHFFFAOYSA-N

物化性质

• 熔点：
  275-276 °C
• 密度：
  1.251±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10,11-Bis(2-fluorophenyl)-9,12-diphenyltetracyclo[6.4.0.04,12.05,9]dodec-10-ene 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 15,24-Diphenylheptacyclo[12.10.0.02,7.08,13.015,19.016,23.020,24]tetracosa-1(14),2,4,6,8,10,12-heptaene 、 3,12-Difluoro-15,24-diphenylheptacyclo[12.10.0.02,7.08,13.015,19.016,23.020,24]tetracosa-1,3,5,7,9,11,13-heptaene 、 3-Fluoro-15,24-diphenylheptacyclo[12.10.0.02,7.08,13.015,19.016,23.020,24]tetracosa-1(14),2(7),3,5,8,10,12-heptaene
  参考文献：
  名称：

  The Synthesis of Rigid Polycyclic Structures for the Study of Diatropic or Steric Effects of a Phenyl Ring on CF Bond

  摘要：

  Polycyclic compounds 1a-c were synthesized to study the diatropic effects of a flanking phenyl ring on nearby CH and CF bonds. F-19 NMR spectra of 1b and 1c were strongly deshielded compared with those of the ring-opened compounds 3b, 7b, and 7c. DMol3 calculations on 1a-c provided quantitative bond lengths and torsional angles to support the conclusion that the downfield shifts in the F-19 NMR spectra are mainly due to steric interactions between the CF bonds and the pi clouds of the phenyl ring(s).

  DOI：

  10.1021/jo402154f
• 作为产物：
  描述：

  1,2-双(2-氟苯基)乙烷-1,2-二酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 10,11-Bis(2-fluorophenyl)-9,12-diphenyltetracyclo[6.4.0.04,12.05,9]dodec-10-ene
  参考文献：
  名称：

  The Synthesis of Rigid Polycyclic Structures for the Study of Diatropic or Steric Effects of a Phenyl Ring on CF Bond

  摘要：

  Polycyclic compounds 1a-c were synthesized to study the diatropic effects of a flanking phenyl ring on nearby CH and CF bonds. F-19 NMR spectra of 1b and 1c were strongly deshielded compared with those of the ring-opened compounds 3b, 7b, and 7c. DMol3 calculations on 1a-c provided quantitative bond lengths and torsional angles to support the conclusion that the downfield shifts in the F-19 NMR spectra are mainly due to steric interactions between the CF bonds and the pi clouds of the phenyl ring(s).

  DOI：

  10.1021/jo402154f

文献信息

• The Synthesis of Rigid Polycyclic Structures for the Study of Diatropic or Steric Effects of a Phenyl Ring on CF Bond
  作者：Yung-Yu Chang、I-Ting Ho、Tse-Lok Ho、Wen-Sheng Chung

  DOI：10.1021/jo402154f

  日期：2013.12.20

  Polycyclic compounds 1a-c were synthesized to study the diatropic effects of a flanking phenyl ring on nearby CH and CF bonds. F-19 NMR spectra of 1b and 1c were strongly deshielded compared with those of the ring-opened compounds 3b, 7b, and 7c. DMol3 calculations on 1a-c provided quantitative bond lengths and torsional angles to support the conclusion that the downfield shifts in the F-19 NMR spectra are mainly due to steric interactions between the CF bonds and the pi clouds of the phenyl ring(s).