5-N,8-N-diphenylquinoxaline-5,8-diamine | 705973-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-N,8-N-diphenylquinoxaline-5,8-diamine
• CAS: 705973-29-1
• 化学式: C₂₀H₁₆N₄
• 分子量: 312.374
• InChiKey: JCPNRNMODVRSPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-N,8-N-diphenylquinoxaline-5,8-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
  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-bis(phenylamino)-2,1,3-benzothiadiazole 在 溶剂黄146 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 28.0h， 生成 5-N,8-N-diphenylquinoxaline-5,8-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

文献信息

• Synthesis and Characterization of <i>p</i>-Phenylenediamine Derivatives Bearing an Electron-Acceptor Unit
  作者：Hidehiro Sakurai、Mendra T. S. Ritonga、Harumi Shibatani、Toshikazu Hirao

  DOI：10.1021/jo048324j

  日期：2005.4.1

  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.