N-(2,4-二硝基苯亚甲基)-4-甲氧基苯胺 | 354538-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2,4-二硝基苯亚甲基)-4-甲氧基苯胺
• 英文名称: N-(2,4-dinitrobenzylidene)-4-methoxyaniline
• 英文别名: Benzenamine, 4-methoxy-N-(2,4-dinitrobenzylidene)-；1-(2,4-dinitrophenyl)-N-(4-methoxyphenyl)methanimine
• CAS: 354538-06-0
• 化学式: C₁₄H₁₁N₃O₅
• mdl: MFCD02646669
• 分子量: 301.258
• InChiKey: MUUZRJUPVBJRCW-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C
• 沸点：
  489.0±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-二硝基苯甲醛 、 甲氧苯胺 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以41%的产率得到N-(2,4-二硝基苯亚甲基)-4-甲氧基苯胺
  参考文献：
  名称：

  A novel strategy for chromogenic chemosensors highly selective toward cyanide based on its reaction with 4-(2,4-dinitrobenzylideneamino)benzenes or 2,4-dinitrostilbenes

  摘要：

  N-(2,4-dinitrobenzylidene)-4-methoxyaniline (1), 4-(N,N-dimethylamine)-N-(2,4-dinitrobenzylidene) aniline (2), 2,4-dinitro-4'-methoxystilbene (3), and 2,4-dinitro-4'-(dimethylamino)stilbene (4) were synthesized and studied in dimethyl sulfoxide in a novel strategy as anionic chromogenic chemosensors. The color of the solutions of these compounds changed only in the presence of cyanide. The kinetic studies were performed with compounds 1-3 in an excess of cyanide. Higher second-order rate constant values were obtained for the compounds containing a methoxy group in relation to the compounds with a dimethylamino substituent, since the methoxy group donates electronic density to the 2,4-dinitrophenyl electron-accepting group less easily compared with the dimethylamino group. Stilbenes generally have greater structural rigidity than imines, facilitating the action of the substituents through the mesomeric effect. The data obtained indicate that the anion acts as a nucleophile, being responsible for C=N bond breaking. The C=C bridge is not broken in the stilbene dyes, but cyanide performs a nucleophilic attack on the 2,4-dinitrophenyl group. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.10.041

文献信息

• Precipitation-driven self-sorting of imines
  作者：Rio Carlo Lirag、Karolina Osowska、Ognjen Š. Miljanić

  DOI：10.1039/c2ob25736j

  日期：——

  Judicious choice of precipitation conditions can lead to self-sorting of equilibrating mixtures of aromatic aldehydes and substituted anilines into a handful of imine products. The selectivity of this process is caused by the solubility differences among possible imines in the EtOH–H2O solvent mixtures used in precipitation.

  明智地选择沉淀条件，可以使处于平衡状态的混合物中芳香醛和取代苯胺自发地分离成少量的亚胺产物。这一过程的选择性源于在用来沉淀的乙醇-水溶剂混合物中可能形成的亚胺之间的溶解度差异所致。
• Four acid-catalysed dehydration reactions proceed without interference
  作者：Rio Carlo Lirag、Ognjen Š. Miljanić

  DOI：10.1039/c4cc02990a

  日期：——

  Four acid-catalysed dehydration reactions can proceed in one pot, simultaneously and without interference, to yield one imine, one acetal (or boronic ester), one ester and one alkene, even though many other cross-products could be conceived. This advanced self-sorting behaviour is attributed to different dehydration rates, brought about by dissimilar electronic properties of starting materials.

  即使可以设想许多其他交叉产物，也可以在一个反应​​釜中同时进行四个酸催化的脱水反应，而不会产生干扰，从而生成一种亚胺，一种乙缩醛（或硼酸酯），一种酯和一种烯烃。这种先进的自选行为归因于不同的脱水速率，这是由起始原料的不同电子特性引起的。
• A novel strategy for chromogenic chemosensors highly selective toward cyanide based on its reaction with 4-(2,4-dinitrobenzylideneamino)benzenes or 2,4-dinitrostilbenes
  作者：Renata S. Heying、Leandro G. Nandi、Adailton J. Bortoluzzi、Vanderlei G. Machado

  DOI：10.1016/j.saa.2014.10.041

  日期：2015.2

  N-(2,4-dinitrobenzylidene)-4-methoxyaniline (1), 4-(N,N-dimethylamine)-N-(2,4-dinitrobenzylidene) aniline (2), 2,4-dinitro-4'-methoxystilbene (3), and 2,4-dinitro-4'-(dimethylamino)stilbene (4) were synthesized and studied in dimethyl sulfoxide in a novel strategy as anionic chromogenic chemosensors. The color of the solutions of these compounds changed only in the presence of cyanide. The kinetic studies were performed with compounds 1-3 in an excess of cyanide. Higher second-order rate constant values were obtained for the compounds containing a methoxy group in relation to the compounds with a dimethylamino substituent, since the methoxy group donates electronic density to the 2,4-dinitrophenyl electron-accepting group less easily compared with the dimethylamino group. Stilbenes generally have greater structural rigidity than imines, facilitating the action of the substituents through the mesomeric effect. The data obtained indicate that the anion acts as a nucleophile, being responsible for C=N bond breaking. The C=C bridge is not broken in the stilbene dyes, but cyanide performs a nucleophilic attack on the 2,4-dinitrophenyl group. (C) 2014 Elsevier B.V. All rights reserved.