4-N-[4-(4-anilinoanilino)phenyl]-7-N-phenyl-2,1,3-benzothiadiazole-4,7-diamine | 507236-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4-N-[4-(4-anilinoanilino)phenyl]-7-N-phenyl-2,1,3-benzothiadiazole-4,7-diamine
• CAS: 507236-63-7
• 化学式: C₃₀H₂₄N₆S
• 分子量: 500.627
• InChiKey: MLPHOBXGHUPCJO-UHFFFAOYSA-N

物化性质

• 沸点：
  761.6±50.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-N-[4-(4-anilinoanilino)phenyl]-7-N-phenyl-2,1,3-benzothiadiazole-4,7-diamine 在 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 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 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 92.0h， 生成 4-N-[4-(4-anilinoanilino)phenyl]-7-N-phenyl-2,1,3-benzothiadiazole-4,7-diamine
  参考文献：
  名称：

  Synthesis and characterization of p-phenylenediamine derivatives bearing a thiadiazole unit

  摘要：

  New p-phenylenediamine derivatives bearing a thiadiazole unit were synthesized by palladium-catalyzed amination. Cyclic voltammetry revealed that the electrochemical properties depend on the position of the benzothiadiazole ring. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02315-8