4-(N,N-dimethylamino)benzaldehyde 4-nitrophenylhydrazone | 3155-30-4

• 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: 4-(N,N-dimethylamino)benzaldehyde 4-nitrophenylhydrazone
• 英文别名: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone；4-dimethylamino-benzaldehyde-(4-nitro-phenylhydrazone)；4-Dimethylamino-benzaldehyd-(4-nitro-phenylhydrazon)；N,N-dimethyl-4-[[(4-nitrophenyl)hydrazinylidene]methyl]aniline
• CAS: 3155-30-4
• 化学式: C₁₅H₁₆N₄O₂
• mdl: MFCD00414453
• 分子量: 284.318
• InChiKey: JTPWXNAHGYPMAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  4-(N,N-dimethylamino)benzaldehyde 4-nitrophenylhydrazone 以 乙腈 为溶剂， 生成 1-(p-Nitro-phenyl)-3-(p-N,N-dimethylamino-phenyl)-7,7a-dihydro-1H-imidazo-<2,1-c>-1,2,4-triazol
  参考文献：
  名称：

  Jugelt, Werner; Grubert, Lutz; Paulss, Verena, Zeitschrift fur Chemie, 1985, vol. 25, # 12, p. 443 - 444

  摘要：

  DOI：
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 4-硝基苯肼 在 氢气 作用下， 以 乙醇 为溶剂， 生成 4-(N,N-dimethylamino)benzaldehyde 4-nitrophenylhydrazone
  参考文献：
  名称：

  硝基苯染料单层改性ITO电极的光电转换

  摘要：

  两性硝基苯染料（C 18 H 37）2 N–C 6 H 4 –CH N–NH–C 6 H 4 –NO 2已由Langmuir– Blodgett（LB）技术。在常规的光电化学电池中研究了光电流的产生。光电流产生的作用谱与LB膜修饰电极的吸收谱一致，表明LB膜中的染料聚集体负责光电流。某些可能影响观察到的光电流的因素，例如O 2的存在，研究了甲基紫（MV 2+）和对苯二酚（H 2 Q）的浓度，pH和偏置电压。提出了在不同条件下产生光电流的机理模型。

  DOI：

  10.1039/a708450a

文献信息

• Arylaldehydes-pentafluorophenyl Hydrazones as Second-order Nonlinear Optical Chromophores: A Novel Approach for Remarkably Defeating the Nonlinearity-transparency Trade-off
  作者：Jianli Hua、Wei Zhang、Zhen Li、Jingui Qin、Yaochun Shen、Yu Zhang、Zuhong Lu

  DOI：10.1246/cl.2002.232

  日期：2002.2

  A series of new arylhydrazone chromophores containing pentafluorophenyl as electronic acceptor are synthesized and found to exhibit significantly blue-shifted absorption in comparison with the corresponding 4-nitrophenyl analogues while keeping β value in the same order, and this may provide a new opportunity for defeating nonlinearity-transparency trade-off in designing second-order nonlinear optical chromophores.

  合成了一系列以五氟苯基为电子受体的新芳基腙发色团，发现与相应的 4-硝基苯基类似物相比，这些发色团在保持 β 值相同的情况下表现出明显的蓝移吸收，这可能为在设计二阶非线性光学发色团时消除非线性-透明度权衡提供了新的机会。
• Diaryl Hydrazones as Multifunctional Inhibitors of Amyloid Self-Assembly
  作者：Béla Török、Abha Sood、Seema Bag、Rekha Tulsan、Sanjukta Ghosh、Dmitry Borkin、Arleen R. Kennedy、Michelle Melanson、Richard Madden、Weihong Zhou、Harry LeVine、Marianna Török

  DOI：10.1021/bi3012059

  日期：2013.2.19

  The design and application of an effective, new class of multifunctional small molecule inhibitors of amyloid self-assembly are described. Several compounds based on the diaryl hydrazone scaffold were designed. Forty-four substituted derivatives of this core structure were synthesized using a variety of benzaldehydes and phenylhydrazines and characterized. The inhibitor candidates were evaluated in multiple assays, including the inhibition of amyloid beta (A beta) fibrillogenesis and oligomer formation and the reverse processes, the disassembly of preformed fibrils and oligomers. Because the structure of the hydrazone-based inhibitors mimics the redox features of the antioxidant resveratrol, the radical scavenging effect of the compounds was evaluated by colorimetric assays against 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals. The hydrazone scaffold was active in all of the different assays. The structure-activity relationship revealed that the substituents on the aromatic rings had a considerable effect on the overall activity of the compounds. The inhibitors showed strong activity in fibrillogenesis inhibition and disassembly, and even greater potency in the inhibition of oligomer formation and oligomer disassembly. Supporting the quantitative fluorometric and colorimetric assays, size exclusion chromatographic studies indicated that the best compounds practically eliminated or substantially inhibited the formation of soluble, aggregated A beta species, as well. Atomic force microscopy was also applied to monitor the morphology of A beta deposits. The compounds also possessed the predicted antioxidant properties; approximately 30% of the synthesized compounds showed a radical scavenging effect equal to or better than that of resveratrol or ascorbic acid.
• Electrochemical synthesis of heterocyclic compounds. 17. Anodic oxidation of hydrazones in the presence of heteroaromatic and Schiff bases
  作者：Esmir Gunic、Ibro Tabakovic

  DOI：10.1021/jo00256a033

  日期：1988.10
• Tabakovic, Ibro; Crljenak, Senka, Heterocycles, 1981, vol. 16, # 5, p. 699 - 702
  作者：Tabakovic, Ibro、Crljenak, Senka

  DOI：——

  日期：——
• Synthesis and properties of pyrazolino[60]fullerene-donor systems
  作者：Eva Espı́ldora、Juan Luis Delgado、Pilar de la Cruz、Antonio de la Hoz、Vicente López-Arza、Fernando Langa

  DOI：10.1016/s0040-4020(02)00552-5

  日期：2002.7

  A series of pyrazolino[60]fullerenes has been prepared in one pot by 1,3-dipolar cycloaddition to C-60 of the corresponding nitrile in-tine, which was generated in situ from the corresponding hydrazone. A range of donors and acceptors were introduced as substituents. Electrochemical and photophysical studies have revealed weak ground-state interactions between the organic addends and the fullerene sphere. Steady-state fluorescence has shown that, in both toluene and benzonitrile solutions, an efficient electron transfer process takes place when a strong donor is attached to the pyrazolino[60]fullerene system. (C) 2002 Elsevier Science Ltd. All rights reserved.