N,N,N-trimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine | 118739-43-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N,N-trimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine
• 英文别名: N-(4-methoxyphenyl)-N,N',N'-trimethyl-1,4-benzenediamine；4-N-(4-methoxyphenyl)-1-N,1-N,4-N-trimethylbenzene-1,4-diamine
• CAS: 118739-43-8
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: JFCHOROETZKIQU-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  408.2±30.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-甲氧基苯基)-二甲胺 、 N-甲基-P-氨基苯甲醚 在 十四烷基硫代乙酸 作用下， 以 硝基甲烷 为溶剂， 反应 0.17h， 以40%的产率得到N,N,N-trimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine
  参考文献：
  名称：

  Oxidative Activation in Aromatic Substitutions. Reactions of N,N-Dimethylanilines with Secondary Anilines Promoted by Thallium Triacetate

  摘要：

  The reactions of N,N-dimethyl-p-anisidine (1a), N,N-dimethylaniline (1b), and N,N-dimethyl-p-fluoroaniline (1c) toward secondary anilines 2(a-d)-H in the presence of thallium triacetate sesquihydrate have been studied as representative of a novel oxidatively activated aromatic substitution affording 1,4-benzenediamine derivatives 3a-d. All of the substrates considered gave substitution with diphenylamine (2d-H). However, with anilines 2b,c-H, only 1a underwent substitution, and substrates 1b,c were practically unreactive. The observed differences in reactivity are well accounted for within a mechanistic framework wherein oxidative activation of both the substrate and the secondary aniline is regarded as alternatively (or simultaneously) possible, depending on the redox characteristics of the reactants. For instance, it can be stated, beyond any reasonable doubt, that reactions of 1a with 2b,c-H proceed via nucleophilic attack of the latter on 1a(+), and that the reaction of 1a-c with 2d-H must involve the diphenylamino radical 2d.

  DOI：

  10.1021/jo982276j

文献信息

• On the ESR identification of paramagnetic species observed during set oxidation of N,N-dimethyl-p-anisidine
  作者：F. Ciminale、R. Curci、M. Portacci、L. Troisi

  DOI：10.1016/s0040-4039(00)87908-3

  日期：——
• Oxidative Activation in Aromatic Substitutions. Reactions of <i>N</i>,<i>N</i>-Dimethylanilines with Secondary Anilines Promoted by Thallium Triacetate
  作者：Francesco Ciminale、Antonella Ciardo、Salvatore Francioso、Angelo Nacci

  DOI：10.1021/jo982276j

  日期：1999.4.1

  The reactions of N,N-dimethyl-p-anisidine (1a), N,N-dimethylaniline (1b), and N,N-dimethyl-p-fluoroaniline (1c) toward secondary anilines 2(a-d)-H in the presence of thallium triacetate sesquihydrate have been studied as representative of a novel oxidatively activated aromatic substitution affording 1,4-benzenediamine derivatives 3a-d. All of the substrates considered gave substitution with diphenylamine (2d-H). However, with anilines 2b,c-H, only 1a underwent substitution, and substrates 1b,c were practically unreactive. The observed differences in reactivity are well accounted for within a mechanistic framework wherein oxidative activation of both the substrate and the secondary aniline is regarded as alternatively (or simultaneously) possible, depending on the redox characteristics of the reactants. For instance, it can be stated, beyond any reasonable doubt, that reactions of 1a with 2b,c-H proceed via nucleophilic attack of the latter on 1a(+), and that the reaction of 1a-c with 2d-H must involve the diphenylamino radical 2d.