(E)-1-(4-methoxybenzylidene)-2-(4-nitrophenyl)hydrazine | 33786-42-4

• 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: (E)-1-(4-methoxybenzylidene)-2-(4-nitrophenyl)hydrazine
• 英文别名: p-Anisaldehyde, (p-nitrophenyl)hydrazone；N-[(E)-(4-methoxyphenyl)methylideneamino]-4-nitroaniline
• CAS: 33786-42-4
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: DGJRRYXJIRLUID-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methoxybenzylidene)-2-(4-nitrophenyl)hydrazine 生成 3,5-bis-(4-methoxyphenyl)-[1,2,4]thiadiazole
  参考文献：
  名称：

  BARTON D. H. R.; BUBB W. A., J. CHEM. SOC. PERKIN TRANS. PART 1 , 1977, NO 8, 916-923

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 4-硝基苯肼 在 sodium acetate 作用下， 以 乙醇 为溶剂， 以87%的产率得到(E)-1-(4-methoxybenzylidene)-2-(4-nitrophenyl)hydrazine
  参考文献：
  名称：

  4-甲氧基苯甲醛衍生的二氯二氮杂二烯的合成与结构研究

  摘要：

  摘要研究了在氯化铜（I）存在下，在四氯化碳的作用下，N-取代的N-甲氧基苯甲醛衍生物转化为相应的1,2-二氮杂丁-1.3-二烯。结果表明，在肼片段中同时含有供体和受体基团的不同性质的可参与该反应。使用3，5-双（三氟甲基）苯基肼衍生物获得了有利于该转化的自由基机理的进一步证据。通过X射线衍射分析研究了合成产物的结构特征。

  DOI：

  10.1134/s1070428020020013

文献信息

• Efficient Synthesis of Fully Substituted and Diversely Functionalized Pyrazoles through <i>p</i>‐TSA Catalyzed One‐Pot Condensation of Cyclic <i>β</i>‐Diketones, Arylglyoxals and Arylhydrazones
  作者：Arun Dhurey、Subhro Mandal、Animesh Pramanik

  DOI：10.1002/ejoc.202300770

  日期：2023.10.21

  An acid catalyzed one-pot condensation of readily available cyclic β-diketones, arylglyoxals and arylhydrazones produces a library of diversely functionalized pyrazole derivatives in excellent yield under metal-catalyst-free benign conditions.

  容易获得的环状β-二酮、芳基乙二醛和芳基腙的酸催化一锅缩合反应在无金属催化剂的良性条件下以优异的产率产生了多种官能化的吡唑衍生物库。
• Anti-Plasmodium activity of tetrazolium salts
  作者：Xilin Cui、Jason Z. Vlahakis、Ian E. Crandall、Walter A. Szarek

  DOI：10.1016/j.bmc.2007.11.005

  日期：2008.2.15

  We have previously reported that sulfated cyclodextrins inhibit the invasion of Plasmodium merozoites by interacting with receptors present on the surface of erythrocytes. The observation that tetrazolium salts formed stable complexes with the inhibitory sulfated cyclodextrins suggested that tetrazolium salts might have anti-Plasmodium activity as well. Evaluation of commercially available tetrazolium salts indicated that some were active in the low nanomolar range and showed specificity in their inhibition of Plasmodium. Synthesis of a further 54 structures allowed us to determine that activity results from an aromatic component attached to the tetrazolium carbon atom (R-1) and its size is not critical to the activity of the compound. Nitro modi. cations of active compounds are poorly tolerated, however, the presence of halogen atoms on aromatic groups attached to the nitrogen atoms of the tetrazolium ring (R-2 and R-3) has little effect on activity. Methoxy groups are tolerated on R-2 and R-3 components; however, they are disruptive on the R-1 component. The overall results suggest that the R-1 component is interacting with a specific hydrophobic environment and the R-2 and R-3 components are less constrained. The activity of these compounds in several human and mouse Plasmodium cultures suggests that the compounds interact with a component of the parasite that is both essential and conserved. (c) 2007 Elsevier Ltd. All rights reserved.
• Aminyl and iminyl radicals from arylhydrazones in the photo-induced DNA cleavage
  作者：Jih Ru Hwu、Chun Chieh Lin、Shih Hsien Chuang、Ke Yung King、Tzu-Rong Su、Shwu-Chen Tsay

  DOI：10.1016/j.bmc.2004.03.037

  日期：2004.5

  Photolytic cleavage of the nitrogen-nitrogen single bond in benzaldehyde phenylhydrazones produced aminyl (R2N) and iminyl (R2C=N) radicals. This photochemical property was utilized in the development of hydrazones as photo-induced DNA-cleaving agents. Irradiation with 350 nm UV light of arylhydrazones bearing substituents of various types in a phosphate buffer solution containing the supercoiled circular phiX174 RFI DNA at pH 6.0 resulted in single-strand cleavage of DNA. Attachment of the electron-donating OMe group to arylhydrazones increased their DNA-cleaving activity. Results from systematic studies indicate that both the aminyl and the iminyl radicals possessed DNA-cleaving ability. (C) 2004 Elsevier Ltd. All rights reserved.
• SINGH, H. B.;MCWHINNIE, W. R., J. CHEM. SOC. DALTON TRANS., 1985, N 4, 821-825
  作者：SINGH, H. B.、MCWHINNIE, W. R.

  DOI：——

  日期：——
• Synthesis and Structural Study of Dichlorodiazadienes Derived from 4-Methoxybenzaldehyde
  作者：N. G. Shikhaliyev、U. F. Askerova、S. H. Mukhtarova、A. A. Niyazova、P. V. Dorovatovskii、V. N. Khrustalev、V. G. Nenajdenko

  DOI：10.1134/s1070428020020013

  日期：2020.2

  hydrazine fragment, can be involved in the reaction. Further evidence in favor of a radical mechanism of this transformation was obtained using a 3,5-bis(trifluoromethyl)phenylhydrazine derivative. The structural features of the synthesized products were studied by X-ray diffraction analysis.

  摘要研究了在氯化铜（I）存在下，在四氯化碳的作用下，N-取代的N-甲氧基苯甲醛衍生物转化为相应的1,2-二氮杂丁-1.3-二烯。结果表明，在肼片段中同时含有供体和受体基团的不同性质的可参与该反应。使用3，5-双（三氟甲基）苯基肼衍生物获得了有利于该转化的自由基机理的进一步证据。通过X射线衍射分析研究了合成产物的结构特征。