1,4-bis(2-fluorophenyl)naphthalene | 1380586-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-bis(2-fluorophenyl)naphthalene
• CAS: 1380586-81-1
• 化学式: C₂₂H₁₄F₂
• 分子量: 316.35
• InChiKey: CPHZLUBHVGBSJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,4-bis(2-fluorophenyl)naphthalene 在 aluminum oxide 作用下， 反应 60.0h， 以34%的产率得到茚并(1,2,3-,C,D)荧蒽
  参考文献：
  名称：

  Intramolecular Aryl–Aryl Coupling of Fluoroarenes through Al₂O₃-Mediated HF Elimination

  摘要：

  A strategy for effective intramolecular aryl-aryl coupling of fluoroarenes through Al2O3-mediated HF elimination is reported. It is demonstrated that the C-F bond, which is widely believed to be the most passive functionality in organic chemistry, can be reconsidered as a useful functional group allowing very effective C-C bond formation. The solid-state strategy presented in this study opens the possibility for facile syntheses of insoluble extended polycyclic aromatic hydrocarbons.

  DOI：

  10.1021/jo300783y
• 作为产物：
  描述：

  1,4-二溴代萘 、 2-氟苯硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.0h， 以71%的产率得到1,4-bis(2-fluorophenyl)naphthalene
  参考文献：
  名称：

  Intramolecular Aryl–Aryl Coupling of Fluoroarenes through Al₂O₃-Mediated HF Elimination

  摘要：

  A strategy for effective intramolecular aryl-aryl coupling of fluoroarenes through Al2O3-mediated HF elimination is reported. It is demonstrated that the C-F bond, which is widely believed to be the most passive functionality in organic chemistry, can be reconsidered as a useful functional group allowing very effective C-C bond formation. The solid-state strategy presented in this study opens the possibility for facile syntheses of insoluble extended polycyclic aromatic hydrocarbons.

  DOI：

  10.1021/jo300783y