苯酚,4-[(E)-[(4-硝基苯基)亚甲基]氨基]- | 129121-76-2

• 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: 苯酚,4-[(E)-[(4-硝基苯基)亚甲基]氨基]-
• 英文名称: 4-{[(4-nitrophenyl)methylene]amino}phenol
• 英文别名: (E)-4-((4-nitrobenzylidene)amino)phenol；4-hydroxy-N-(4-nitrobenzylidene)aniline；(E)-4-(4-nitrobenzylideneamino)phenol；N-(4-Nitrobenzyliden)-4-hydroxyanilin
• CAS: 129121-76-2
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: SLHOVHNNONKHGF-NTEUORMPSA-N

物化性质

• 熔点：
  168 °C
• 沸点：
  459.8±30.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.73
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯酚,4-[(E)-[(4-硝基苯基)亚甲基]氨基]- 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-((4-nitrophenyl)-4-oxo-3-phenoxyazetidin-1-yl)phenyl acrylate
  参考文献：
  名称：

  Synthesis and antimalarial activity of new nanocopolymer β-lactams and molecular docking study of their monomers

  摘要：

  This report describes the preparation of some new beta-lactam nanocopolymers. These nanoparticles are synthesized in water by emulsion polymerization of an acrylate beta-lactam pre-dissolved in a mixture of co-monomers in the presence of sodium dodecyl sulfate as a surfactant and potassium persulfate as a radical initiator. Dynamic light scattering analysis and electron microscopy images of these emulsions show that the nanoparticles are approximately 30-70 nm in diameter. These compounds have been evaluated for their antimalarial activities against chloroquine-resistant Plasmodium faliparum K1 strain demonstrating IC50 varying from 14 to 50 A mu M. The interactions between these beta-lactam nanocopolymers and the P. falciparum single-stranded DNA-binding proteins have been studied by molecular docking calculations.

  DOI：

  10.1007/s00044-015-1477-7
• 作为产物：
  描述：

  对氨基苯酚 、 对硝基苯甲醛 生成 苯酚,4-[(E)-[(4-硝基苯基)亚甲基]氨基]-
  参考文献：
  名称：

  Modeling Substituent-Dependence of the Twist and Shielding in a Series of 4-Substituted N-(4-Nitrobenzylidene)anilines

  摘要：

  一系列15个4-取代N-(4-硝基苯甲基亚胺)苯胺经过合成并通过1H核磁共振光谱进行研究。它们的从头算几何结构以及由芳香环电流表示的屏蔽效应被用于相关性分析。几何结构完全优化使用密度泛函理论B3LYP/6-311G**方法。为了确定环电流对偶氮甲基氢Hα屏蔽的贡献，使用了在模型体系中直接从头算化学屏蔽的计算。实验化学位移值中不包含这些贡献的部分成功地与对单取代苯乙烯的化学位移增量ap相关联。以相同的方式，计算了C=N双键对Hm氢的各向异性贡献，并且不包含这种贡献的Hm化学位移值成功地与化学位移增量am相关联。

  DOI：

  10.1135/cccc20041566

文献信息

• Synthesis and molecular docking studies of imines as α-glucosidase and α-amylase inhibitors
  作者：Analy Aispuro-Pérez、Juan López-Ávalos、Fernando García-Páez、Julio Montes-Avila、Lorenzo A. Picos-Corrales、Adrián Ochoa-Terán、Pedro Bastidas、Sarita Montaño、Loranda Calderón-Zamora、Ulises Osuna-Martínez、Juan I. Sarmiento-Sánchez

  DOI：10.1016/j.bioorg.2019.103491

  日期：2020.1

  (E)-1-phenyl-N-(pyridin-2-yl)methanimine (3c) displayed similar activity that acarbose against α-glucosidase. The molecular docking studies in α-glucosidase and α-amylase reveal that aryl imines mainly establish an H-bond with the R2-subtituent and hydrophobic interactions with the R1-subtituent. The docking analysis reveals these synthetic aryl imines 3d-i interact in same active site than acarbose drug in

  在具有重要生物活性的许多化合物中发现亚胺功能。因此，开发新的亚胺合成方法很重要。在这项工作中，提出了在氧化铝-硫酸催化的微波辐射下芳基亚胺的简单，环保和直接的合成途径。另外，进行了体外酶抑制，抗氧化活性和分子对接研究。分离出芳基亚胺，产率为37-94％。评价所有合成的芳基亚胺在体外对α-葡糖苷酶和α-淀粉酶的抑制潜力，结果表明大多数化合物对两种酶均表现出抑制活性。（E）-1-（4-硝基苯基）-N-（吡啶-2-基）甲亚胺（3d）为1。抗α-淀粉酶的活性比阿卡波糖高15倍，而（E）-1-苯基-N-（吡啶-2-基）甲亚胺（3c）的活性类似于阿卡波糖对α-葡糖苷酶的活性。对α-葡萄糖苷酶和α-淀粉酶的分子对接研究表明，芳基亚胺主要与R2取代基建立H键，并与R1取代基发生疏水相互作用。对接分析显示，在两种酶中，这些合成的芳基亚胺3d-i在与阿卡波糖药物相同的活性位点相互作用。
• Effect of media polarity on the photoisomerisation of substituted stilbene, azobenzene and imine chromophores
  作者：N. R. King、Eric A. Whale、Fred J. Davis、Andrew Gilbert、Geoffrey R. Mitchell

  DOI：10.1039/a607980f

  日期：——

  The influence of substituents and media polarity on the photoinducedE→Z geometrical isomerisation of the stilbene, azobenzene and N-benzylideneaniline chromophores has been compared and assessed. The efficiency of the process in all three systems is markedly dependent on the presence and characteristics of electron-donor and electron-acceptor substituents at the 4- and 4′-positions. The results are discussed in terms of relaxation of the E-excited singlet state. In the absence of a nitro substituent, relaxation to the S 1 orthogonal state competes effectively with non-productive intramolecular electron transfer; in the presence of a nitro substituent, the T 1 orthogonal state is formed from inter-system crossing. For systems with a 4-nitro and a 4′-electron-donor substituent, access to the triplet state is inhibited by polar solvents promoting formation of the inactive charge-transfer state from the S 1 state, and no isomerisation is observed. Similar effects are observed in both solution and polymer films. Such variations in behaviour have important implications for the utilisation of the chromophores in nonlinear optical phenomena including photorefractivity.

  我们比较并评估了取代基和介质极性对二苯乙烯、偶氮苯和 N-亚苄基苯胺发色团的光诱导 E→Z 几何异构化的影响。在所有这三个系统中，该过程的效率明显取决于 4-和 4′-位置上电子供体和电子受体取代基的存在和特性。我们从 E 激发单态的弛豫角度对结果进行了讨论。在没有硝基取代基的情况下，向 S 1 正交态的弛豫与非生产性的分子内电子转移有效竞争；在有硝基取代基的情况下，T 1 正交态是由体系间的交叉形成的。对于具有 4-硝基和 4′-电子供体取代基的体系，极性溶剂会抑制三重态的进入，从而促进从 S 1 态形成非活性电荷转移态，并且不会观察到异构化现象。在溶液和聚合物薄膜中也观察到类似的效应。这种行为变化对利用发色团产生非线性光学现象（包括光折射）具有重要意义。
• Dual colorimetric receptor with logic gate operations: anion induced solvatochromism
  作者：Madhuprasad、N. Swathi、J. R. Manjunatha、Uttam Kumar Das、A. Nityananda Shetty、Darshak R. Trivedi

  DOI：10.1039/c3nj01229h

  日期：——

  A receptor R1 was designed and synthesised for colorimetric detection of F− ions as well as Cu2+ ions via intramolecular charge transfer mechanism. Upon addition of F− ions in dry DMSO, the color of the receptor R1 changed from pale yellow to blue. The receptor showed a unique property of solvatochromism by displaying different coloration with different solvents only in the presence of F− ions, which were applied to determine the percentage composition of binary solvent mixtures. The receptor R1 was able to detect Cu2+ ions colorimetrically where it exhibited a color change from pale yellow to orange-red. In addition, the receptor was subjected to molecular logic gate applications, wherein it showed ‘ON–OFF’ switching operations.

  设计并合成了受体 R1，用于通过分子内电荷转移机制对 F− 离子和 Cu2+ 离子进行比色检测。在干燥 DMSO 中添加 F− 离子后，受体 R1 的颜色从浅黄色变为蓝色。该受体显示出溶剂化显色的独特性质，仅在 F− 离子存在的情况下，不同溶剂显示出不同的颜色，这可用于确定二元溶剂混合物的百分比组成。受体 R1 能够通过比色法检测 Cu2+ 离子，其颜色从浅黄色变为橙红色。此外，该受体还接受了分子逻辑门应用，显示出“ON-OFF”开关操作。
• ZAGNIJ V. V.; SIROMYATNIKOV V. G., VISNIK KIIV. YH-TY. XIMIYA, 1979, HO 20, 56-60
  作者：ZAGNIJ V. V.、 SIROMYATNIKOV V. G.

  DOI：——

  日期：——
• Organic nonlinear optical material
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0250099B1

  公开（公告）日：1993-01-27