(Z,Z)-N,N'-bis(1-[4-bromophenyl]-4,4,4-trifluoro-3-oxo-1-buten-1-yl)-1,3-phenylenediamine | 1344681-08-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z,Z)-N,N'-bis(1-[4-bromophenyl]-4,4,4-trifluoro-3-oxo-1-buten-1-yl)-1,3-phenylenediamine
• CAS: 1344681-08-8
• 化学式: C₂₆H₁₆Br₂F₆N₂O₂
• 分子量: 662.224
• InChiKey: WNXUSSYNPLESJB-JZTLMNBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.38
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z,Z)-N,N'-bis(1-[4-bromophenyl]-4,4,4-trifluoro-3-oxo-1-buten-1-yl)-1,3-phenylenediamine 在 四磷十氧化物 、 磷酸 作用下， 反应 36.0h， 以33%的产率得到2,10-di(4-bromophenyl)-4,8-bis(trifluoromethyl)-1,7-phenanthroline
  参考文献：
  名称：

  Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

  摘要：

  This paper reports interesting results of the conventional synthesis of a new series of 2,10-dialkyl(aryl)-4,8-bis(trifluoromethyl)-1,7-phenanthrolines, in 22-40% yields, from cyclization reactions of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines [1,3-C6H4-(NHCR=CHC(O)CF3)(2)] in a strongly acidic medium (PPA) and absence of solvent. The synthetic route also allowed the isolation of a new series of 2-alkyl(aryl/heteroaryl)-4-trifluoromethyl-7-aminoquinolines, in 20-73% yields, simultaneously. The enaminone precursors were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R)OR1, where R = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furyl and R-1 = Me, Et] with 1,3-phenylenediamine under mild conditions, in 47-91% yields.

  DOI：

  10.1590/s0103-50532011000800005
• 作为产物：
  描述：

  间苯二胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到(Z,Z)-N,N'-bis(1-[4-bromophenyl]-4,4,4-trifluoro-3-oxo-1-buten-1-yl)-1,3-phenylenediamine
  参考文献：
  名称：

  Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

  摘要：

  This paper reports interesting results of the conventional synthesis of a new series of 2,10-dialkyl(aryl)-4,8-bis(trifluoromethyl)-1,7-phenanthrolines, in 22-40% yields, from cyclization reactions of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines [1,3-C6H4-(NHCR=CHC(O)CF3)(2)] in a strongly acidic medium (PPA) and absence of solvent. The synthetic route also allowed the isolation of a new series of 2-alkyl(aryl/heteroaryl)-4-trifluoromethyl-7-aminoquinolines, in 20-73% yields, simultaneously. The enaminone precursors were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R)OR1, where R = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furyl and R-1 = Me, Et] with 1,3-phenylenediamine under mild conditions, in 47-91% yields.

  DOI：

  10.1590/s0103-50532011000800005