N1-phenyl-N4-(4-(((4E,7E)-7-(phenylimino)benzo[c][1,2,5]thiadiazol-4(7H)-ylidene)amino)phenyl)benzene-1,4-diamine | 850130-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N1-phenyl-N4-(4-(((4E,7E)-7-(phenylimino)benzo[c][1,2,5]thiadiazol-4(7H)-ylidene)amino)phenyl)benzene-1,4-diamine
• CAS: 850130-77-7
• 化学式: C₃₀H₂₂N₆S
• 分子量: 498.611
• InChiKey: RRMGCYYUWHHRRN-SWMYPXFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.56
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N1-phenyl-N4-(4-(((4E,7E)-7-(phenylimino)benzo[c][1,2,5]thiadiazol-4(7H)-ylidene)amino)phenyl)benzene-1,4-diamine 在 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以100%的产率得到7-N-phenyl-4-N-[4-[(4-phenyliminocyclohexa-2,5-dien-1-ylidene)amino]phenyl]-2,1,3-benzothiadiazole-4,7-diimine
  参考文献：
  名称：

  Synthesis and Characterization of p-Phenylenediamine Derivatives Bearing an Electron-Acceptor Unit

  摘要：

  Two series of aniline oligomers bearing fused heterocycles as an electron-acceptor unit were synthesized. They consist of aniline or its derivatives as an electron donor and benzothiadiazole (BT) or quinoxaline (QX) as an electron-acceptor unit. Benzothiadiazoles 1-3 were synthesized by palladium-catalyzed amination. Quinoxalines 4-6 were prepared by palladium-catalyzed amination or transformation from the benzothiadiazoles. These compounds showed a HOMO-LUMO gap smaller than those of their analogues such as thiophene-substituted BT/QXs. Cyclic voltammetry revealed that the electrochemical behavior is dependent on the position of the acceptor heterocycle. Chemical oxidation with Ag2O afforded the corresponding 1,4-quinonediimine derivatives as an E,E-isomer, stereoselectively. As for the BT pentamer analogues 2 and 3, the first oxidation selectively occurred at the amino group adjacent to the benzothiadiazole unit, giving the regiospecific half-oxidized derivatives. Furthermore, the fully oxidized derivative 24 was isolated and characterized.

  DOI：

  10.1021/jo048324j
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 在 palladium diacetate 双(2-二苯基磷苯基)醚 、 silver(l) oxide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 104.0h， 生成 N1-phenyl-N4-(4-(((4E,7E)-7-(phenylimino)benzo[c][1,2,5]thiadiazol-4(7H)-ylidene)amino)phenyl)benzene-1,4-diamine
  参考文献：
  名称：

  Synthesis and Characterization of p-Phenylenediamine Derivatives Bearing an Electron-Acceptor Unit

  摘要：

  Two series of aniline oligomers bearing fused heterocycles as an electron-acceptor unit were synthesized. They consist of aniline or its derivatives as an electron donor and benzothiadiazole (BT) or quinoxaline (QX) as an electron-acceptor unit. Benzothiadiazoles 1-3 were synthesized by palladium-catalyzed amination. Quinoxalines 4-6 were prepared by palladium-catalyzed amination or transformation from the benzothiadiazoles. These compounds showed a HOMO-LUMO gap smaller than those of their analogues such as thiophene-substituted BT/QXs. Cyclic voltammetry revealed that the electrochemical behavior is dependent on the position of the acceptor heterocycle. Chemical oxidation with Ag2O afforded the corresponding 1,4-quinonediimine derivatives as an E,E-isomer, stereoselectively. As for the BT pentamer analogues 2 and 3, the first oxidation selectively occurred at the amino group adjacent to the benzothiadiazole unit, giving the regiospecific half-oxidized derivatives. Furthermore, the fully oxidized derivative 24 was isolated and characterized.

  DOI：

  10.1021/jo048324j