N,N-dimethyl-4-[(4-nitrophenyl)methylideneamino]aniline | 111955-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dimethyl-4-[(4-nitrophenyl)methylideneamino]aniline
• 英文别名: N,N-dimethyl-N'-<(4-nitrophenyl)methylene>-1,4-benzenediamine；(Z)-N,N-dimethyl-4-((4-nitrobenzylidine)amino)aniline；syn-N,N-Dimethyl-N'--p-phenylendiamin；syn-N,N-Dimethyl-N'-(p-nitro-benzal)-p-phenylendiamin
• CAS: 111955-89-6
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: OYAKOCHANTYBKA-WJDWOHSUSA-N

物化性质

• 沸点：
  451.8±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.74
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-4-[(4-nitrophenyl)methylideneamino]aniline 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以66%的产率得到N₁,N₁-dimethyl-N₄-(4-nitrobenzyl)benzene-1,4-diamine
  参考文献：
  名称：

  단백질 키나아제 저해제인 벤즈아미드 유도체

  摘要：

  这项发明涉及具有蛋白激酶抑制活性的苯甲酰胺化合物，其药学上可接受的盐，以及包含该化合物作为有效成分的用于预防和治疗由异常细胞生长引起的疾病的药学组合物。这些新型化合物对于主要诱发因素如PDHK蛋白激酶的疾病，如糖尿病、肥胖、癌症等，表现出优越的抑制作用，因此对于由这些蛋白激酶引起的异常细胞生长和代谢引起的疾病的预防和治疗剂是有用的。

  公开号：

  KR20200066463A
• 作为产物：
  描述：

  对硝基苯甲醛 、 N,N-二甲基-对苯二胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以83%的产率得到N,N-dimethyl-4-[(4-nitrophenyl)methylideneamino]aniline
  参考文献：
  名称：

  단백질 키나아제 저해제인 벤즈아미드 유도체

  摘要：

  这项发明涉及具有蛋白激酶抑制活性的苯甲酰胺化合物，其药学上可接受的盐，以及包含该化合物作为有效成分的用于预防和治疗由异常细胞生长引起的疾病的药学组合物。这些新型化合物对于主要诱发因素如PDHK蛋白激酶的疾病，如糖尿病、肥胖、癌症等，表现出优越的抑制作用，因此对于由这些蛋白激酶引起的异常细胞生长和代谢引起的疾病的预防和治疗剂是有用的。

  公开号：

  KR20200066463A

文献信息

• New Kinetic Evidence for Inversional Mechanism in Thermal Geometrical Isomerization about Carbon–Nitrogen Double Bond
  作者：Tsutomu Asano、Toshio Okada

  DOI：10.1246/cl.1987.691

  日期：1987.4.5

  Kinetic pressure and solvent effects were studied for geometrical isomerization about carbon-nitrogen double bond in N,N-dimethyl-N′-[(4-nitrophenyl)methylene]-1,4-benzenediamine and 4-[[4-(dimethylamino)phenyl]imino]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. In both of the compounds, the effects clearly demonstrate that the polarity of the reactant decreases slightly during activation, and the

  研究了N,N-二甲基-N'-[(4-硝基苯基)亚甲基]-1,4-苯二胺和4-[[4-(二甲氨基)苯基]亚氨基]-2,4-二氢-5-甲基-2-苯基-3H-吡唑-3-one。在这两种化合物中，效果清楚地表明，在活化过程中反应物的极性略有下降，结果很难与先前提出的旋转机制相一致。
• Mechanism of thermal Z/E isomerization of substituted N-benzylideneanilines. Nature of the activated complex with an sp-hybridized nitrogen atom
  作者：Tsutomu Asano、Hiroyuki Furuta、Hans Joerg Hofmann、Renzo Cimiraglia、Yuho Tsuno、Mizue Fujio

  DOI：10.1021/jo00068a042

  日期：1993.7

  In order to study the mechanism of thermal geometrical isomerization involving a sp2-hybridized nitrogen atom, kinetic effects of substituent, solvent, and pressure were studied in substituted N-benzylideneanilines. The effect of the substituent on the aniline moiety was almost independent of the electronic nature of the benzylidene group, and the results could be described satisfactorily by log (k/k(o)) = rho[sigma-degrees + r+(sigma+-sigma-degrees)+ r-(sigma--sigma-degrees)], except for the 4-(dimethylamino) group. The r- values were more than twice as large as r+, suggesting strongly that the aniline ring is in conjugation not with the carbon-nitrogen pi bond but with the nitrogen lone pair in the transition state. The lower activation enthalpies and fairly large negative activation entropies observed in N-(4-X-benzylidene)4-nitroanilines also support this view. When a dimethylamino group exists in the 4-position of the aniline ring, the rate constants observed were larger than that expected from the above equation. This deviation suggests the existence of a reaction route where the two phenyl groups become coplanar in the transition state. Ab initio calculations on selected N-phenylformaldimines and N-benzylideneanilines were performed to characterize the actual relation between both reaction possibilities as alternative and parallel routes, respectively. On the basis of the experimental data, the rate constants for the two inversion isomerizations were estimated by assuming parallel reactions for three cases.
• Mechanism of geometrical isomerization about the carbon-nitrogen double bond
  作者：Tsutomu Asano、Toshio Okada、William G. Herkstroeter

  DOI：10.1021/jo00263a022

  日期：1989.1