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 | 1507349-14-5

• 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: 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
• 英文别名: 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
• CAS: 1507349-14-5
• 化学式: C₃₆H₂₈F₂
• 分子量: 498.615
• InChiKey: FEUZSPLGDFISAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  10.0
• 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

• 作为产物：
  描述：

  1,2-双(2-氟苯基)乙烷-1,2-二酮 在 碘 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 32.5h， 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

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).