2,3-Dianilinophenazin | 23677-14-7

• 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: 2,3-Dianilinophenazin
• 英文别名: 2,3-(diphenylamino)phenazine；N,N'-diphenyl-phenazine-2,3-diamine；N²,N³-diphenyl-phenazine-2,3-diyldiamine；N²,N³-Diphenyl-phenazin-2,3-diyldiamin；2-N,3-N-diphenylphenazine-2,3-diamine
• CAS: 23677-14-7
• 化学式: C₂₄H₁₈N₄
• 分子量: 362.434
• InChiKey: JPQQFIWDUXAJNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• 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

• 作为产物：
  描述：

  2-氨基苯酚 在 乙醇 、 溶剂黄146 、 silver(l) oxide 作用下， 生成 2,3-Dianilinophenazin
  参考文献：
  名称：

  铜-胺络合物的氧化-VI：芳族胺尤其是苯胺的氧化

  摘要：

  发现苯胺（在酒精溶液中）在铜离子（含络合物）的催化作用下，会受到氧的邻位氧化。该反应与先前研究的酚的催化邻位氧化反应显示出类比，但也存在一些特征差异。产物是2-氨基-5-苯胺基-醌-4-苯胺（70％），偶氮苯（19％）和3-氨基苯恶唑酮（5％）。通过在Al 2 O 3上的色谱法分离出第四种，至今仍未鉴定。研究了反应范围和取代基的影响。考虑可能的反应机理。

  DOI：

  10.1016/0040-4020(58)88048-5

文献信息

• Kehrmann; Cordone, Chemische Berichte, 1913, vol. 46, p. 3011
  作者：Kehrmann、Cordone

  DOI：——

  日期：——
• Characterization of Reaction Intermediate Aggregates in Aniline Oxidative Polymerization at Low Proton Concentration
  作者：Zhongfen Ding、Timothy Sanchez、Andrea Labouriau、Srinivas Iyer、Toti Larson、Robert Currier、Yusheng Zhao、Dali Yang

  DOI：10.1021/jp102623z

  日期：2010.8.19

  Aggregates of reaction intermediates form during the early stages of aniline oxidative polymerization whenever the initial mole ratio of proton concentration to aniline monomer concentration is low ([H(+)](0)/[An](0) <= 1.0). Detailed characterization is carried out on those aggregates. The intermediate aggregates show a UV-Vis absorption peak at around 410 nm when dispersed in aqueous solution, whereas the peak is centered on 370 nm when dissolved in an organic solvent such as N-methylpyrrolidone. The electronic band gap decreases when the intermediates aggregate to form a solid, and thus, the absorption peak is red-shifted. Gel permeation chromatography (GPC) shows the aggregates contain a major low molecular weight peak with a long tail. The oligoanilines with low molecular weights consistently show a UV-Vis absorption peak at around 370 nm. Mass spectrometry confirms that the intermediate aggregates contain mainly a component with mass number 363 (M + H(+)), likely a tetramer. UV-Vis, GPC, mass spectrometry, NMR, FTIR, and XRD characterization results are presented and chemical structures for the tetramer are proposed. The major components of the intermediate aggregates are likely highly symmetric phenazine- and dihydrophenazine-containing structures. These particular organic compounds have not been identified before as intermediates. The aggregation and precipitation of the tetramers apparently stabilizes these intermediates. The aggregates are highly crystalline, as evidenced by powder X-ray diffraction. A new reaction mechanism for the formation of these intermediates is proposed.
• Oxidations with copper-amine complexes-VI
  作者：G. Engelsma、E. Havinga

  DOI：10.1016/0040-4020(58)88048-5

  日期：1958.5

  Aniline—in alcoholic solutions—was found to undergo ortho-oxidation by oxygen under the catalytic influence of (complexes containing) copper ions. The reaction shows analogy, but also some characteristic differences, with the catalytic ortho-oxidation reactions of phenols studied previously. The products were 2-amino-5-anilino-quinone-4-anil (70%), azobenzene (19%) and 3-aminophenoxazone (5%). A fourth

  发现苯胺（在酒精溶液中）在铜离子（含络合物）的催化作用下，会受到氧的邻位氧化。该反应与先前研究的酚的催化邻位氧化反应显示出类比，但也存在一些特征差异。产物是2-氨基-5-苯胺基-醌-4-苯胺（70％），偶氮苯（19％）和3-氨基苯恶唑酮（5％）。通过在Al 2 O 3上的色谱法分离出第四种，至今仍未鉴定。研究了反应范围和取代基的影响。考虑可能的反应机理。

表征谱图