2-(perfluorophenyl)-4-phenyl-2,3-dihydro-1H-benzo-1,5-diazepine | 1610621-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 2-(perfluorophenyl)-4-phenyl-2,3-dihydro-1H-benzo-1,5-diazepine
• 英文别名: 2-pentafluorophenyl-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepine；2-(2,3,4,5,6-pentafluorophenyl)-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepine
• CAS: 1610621-75-4
• 化学式: C₂₁H₁₃F₅N₂
• 分子量: 388.34
• InChiKey: BGALBTSFYQKVSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(perfluorophenyl)-4-phenyl-2,3-dihydro-1H-benzo-1,5-diazepine 以 异丙醇 为溶剂， 反应 2.0h， 以81%的产率得到1,2,3,4-tetrafluoro-6a-phenyl-6a,7-dihydrobenzimidazo[1,2-a]quinoline
  参考文献：
  名称：

  Polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines: Synthesis and new rearrangement into polyfluorodihydrobenzimidazo[1,2-a]quinolines

  摘要：

  Interaction of polyfluorinated chalcones (pentafluorobenzalacetophenone, benzalpentafluoroacetophenone and decafluorochalcone) with 1,2-diaminobenzene in alcohols in the presence of triethylamine or quaternary ammonium salt (TEBAC) has been investigated. In the presence of TEBAC in 2-propanol polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines are formed. Some of them undergo intramolecular fluorine substitution and unusual rearrangement into a previously unknown polyfluoro-containing tetracyclic compounds-(6aR)-1,2,3,4-tetrafluoro-6a-aryl-6a,7-dihydrobenzimidazo[1,2-a]quinolines, under the reaction conditions as well as in absence of TEBAC. The structures are established on NMR spectra and confirmed by X-ray. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.03.013
• 作为产物：
  描述：

  3-(pentafluorophenyl)-1-phenylprop-2-en-1-one 、 邻苯二胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 28.0h， 以67%的产率得到2-(perfluorophenyl)-4-phenyl-2,3-dihydro-1H-benzo-1,5-diazepine
  参考文献：
  名称：

  Polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines: Synthesis and new rearrangement into polyfluorodihydrobenzimidazo[1,2-a]quinolines

  摘要：

  Interaction of polyfluorinated chalcones (pentafluorobenzalacetophenone, benzalpentafluoroacetophenone and decafluorochalcone) with 1,2-diaminobenzene in alcohols in the presence of triethylamine or quaternary ammonium salt (TEBAC) has been investigated. In the presence of TEBAC in 2-propanol polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines are formed. Some of them undergo intramolecular fluorine substitution and unusual rearrangement into a previously unknown polyfluoro-containing tetracyclic compounds-(6aR)-1,2,3,4-tetrafluoro-6a-aryl-6a,7-dihydrobenzimidazo[1,2-a]quinolines, under the reaction conditions as well as in absence of TEBAC. The structures are established on NMR spectra and confirmed by X-ray. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.03.013

文献信息

• Polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines: Synthesis and new rearrangement into polyfluorodihydrobenzimidazo[1,2-a]quinolines
  作者：Elena A. Borodina、Natalia A. Orlova、Irina Yu. Kargapolova、Yury V. Gatilov

  DOI：10.1016/j.jfluchem.2014.03.013

  日期：2014.6

  Interaction of polyfluorinated chalcones (pentafluorobenzalacetophenone, benzalpentafluoroacetophenone and decafluorochalcone) with 1,2-diaminobenzene in alcohols in the presence of triethylamine or quaternary ammonium salt (TEBAC) has been investigated. In the presence of TEBAC in 2-propanol polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines are formed. Some of them undergo intramolecular fluorine substitution and unusual rearrangement into a previously unknown polyfluoro-containing tetracyclic compounds-(6aR)-1,2,3,4-tetrafluoro-6a-aryl-6a,7-dihydrobenzimidazo[1,2-a]quinolines, under the reaction conditions as well as in absence of TEBAC. The structures are established on NMR spectra and confirmed by X-ray. (C) 2014 Elsevier B.V. All rights reserved.
• Reactions of polyfluorochalcones with o- and p-phenylenediamines. Synthesis and intramolecular transformations of polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines
  作者：E. A. Borodina、N. A. Orlova

  DOI：10.1134/s1070428015020207

  日期：2015.2

  Polyfluorochalcones react with o-phenylenediamine in ethanol and 2-propanol in the presence of triethylamine or benzyltriethylammonium chloride (TEBAC) affording polyfluorinated 2,4-diaryl-2,3-dihydrobenzo-1H-1,5-diazepines. Along with the latter in the presence of triethylamine Michael aza-adducts presumably formed, and at the use of TEBAC in 2-propanol products of intramolecular cyclization and rearrangement of benzo-1,5-diazepines, dihydrobenzimidazo[1,2-a]quinolines were obtained. The reactions of polyfluorochalcones with p-phenylenediamine in ethanol or DMF proceed mostly with the substitution of the para-fluorine atom in the perfluorophenyl rings.