3,4-Bis(2-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dien-1-one | 1507349-12-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-Bis(2-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dien-1-one
• 英文别名: 3,4-bis(2-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dien-1-one
• CAS: 1507349-12-3
• 化学式: C₂₉H₁₈F₂O
• 分子量: 420.458
• InChiKey: RKOISDMFMQMSQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Bis(2-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dien-1-one 、 1,5-环辛二烯 反应 24.0h， 以68%的产率得到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
• 作为产物：
  描述：

  1,2-双(2-氟苯基)-2-羟基乙酮 在 copper diacetate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 3,4-Bis(2-fluorophenyl)-2,5-diphenylcyclopenta-2,4-dien-1-one
  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).