2-hydroxy-5-((3-nitrophenyl)diazenyl)benzaldehyde | 38501-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-hydroxy-5-((3-nitrophenyl)diazenyl)benzaldehyde
• 英文别名: 3-[2-(3-Nitrophenyl)hydrazinylidene]-6-oxocyclohexa-1,4-diene-1-carbaldehyde；2-hydroxy-5-[(3-nitrophenyl)diazenyl]benzaldehyde
• CAS: 38501-88-1
• 化学式: C₁₃H₉N₃O₄
• 分子量: 271.232
• InChiKey: KQQSJXWPCLMASK-UHFFFAOYSA-N

物化性质

• 沸点：
  477.9±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-((3-nitrophenyl)diazenyl)benzaldehyde 在 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 (3S,4R)-1-(4-bromophenyl)-3-chloro-4-[2-hydroxy-5-[(Z)-(3-nitrophenyl)azo]phenyl]azetidin-2-one
  参考文献：
  名称：

  N/C-4 substituted azetidin-2-ones: Synthesis and preliminary evaluation as new class of antimicrobial agents

  摘要：

  A series of 3-chloro-4-(3-methoxy-4-acetyloxyphenyl)-1-[3-oxo-3-(phenylamino)propanamido] azetidin-2-ones 3a-g and 3-chloro-4-[2-hydroxy-5-(nitro substituted phenylazo)phenyll-1-phenylazetidin-2-ones 6a-h were synthesized using appropriate synthetic route. Structures of all the synthesized compounds were established on the basis of elemental analysis and spectroscopic data. The antimicrobial activity of the synthesized compounds was screened against several microbes. Several of these molecules showed potent antimicrobial activity against Bacillus anthracis, Staphyococcus aureus and Candida albicans and significant structure-activity relationship (SAR) trends. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.064
• 作为产物：
  描述：

  氯仿 、 3'-Nitro-4-hydroxy-azobenzol 在 sodium hydroxide 作用下， 生成 2-hydroxy-5-((3-nitrophenyl)diazenyl)benzaldehyde
  参考文献：
  名称：

  Sen; Banerji, Journal of the Indian Chemical Society, 1935, vol. 12, p. 293,295,296,299

  摘要：

  DOI：

文献信息

• Efficient synthesis and anti-bovine viral diarrhea virus evaluation of 5-(aryldiazo)salicylaldehyde thiosemicarbazone derivatives
  作者：Samir Y. Abbas、Wahid M. Basyouni、Khairy A. M. El-Bayouki、Reham M. Dawood、Tawfeek H. Abdelhafez、Mostafa K. Elawady

  DOI：10.1080/00397911.2019.1626893

  日期：2019.9.17

  Abstract An efficient procedure for the synthesis of 5-(aryldiazo)salicylaldehyde thiosemicarbazone derivatives 1-25 was achieved via the condensation of 5-(aryldiazo)salicylaldehyde derivatives I–V with N-(4)-substituted thiosemicarbazide derivatives. Antiviral activity of the synthesized compounds was carried out. From the obtained results, it was noticed that compound 11 has a strong antiviral activity

  摘要 通过将 5-（芳基重氮）水杨醛衍生物 I-V 与 N-（4）-取代的缩氨基硫脲衍生物缩合，实现了合成 5-（芳基重氮）水杨醛缩氨基硫脲衍生物 1-25 的有效方法。进行了合成化合物的抗病毒活性。从得到的结果可以看出，化合物11具有很强的抗病毒活性。图形概要
• New 1,2,4-triazole-based azo–azomethine dyes. Part II: Synthesis, characterization, electrochemical properties and computational studies
  作者：Hamid Khanmohammadi、Malihe Erfantalab、Atena Bayat、Ali Babaei、Masoud Sohrabi

  DOI：10.1016/j.saa.2012.07.041

  日期：2012.11

  monoiminated 1,2,4-triazole-based azo-azomethine dyes have been synthesized via condensation reaction of 4-amino-3-methyl-5-mercapto-1,2,4-triazole with various substituted azo-coupled salicylaldehyde. The dyes have been characterized by using FT-IR, UV-Vis and (1)H NMR spectroscopic methods as well as elemental analysis. The electrochemical behavior of the dyes has been investigated by cyclic voltammetry

  通过4-氨基-3-甲基-5-巯基-1,2,4-三唑与各种取代的偶氮偶合的缩合反应合成了一系列新的单胺化1,2,4-三唑基偶氮-甲亚胺染料水杨醛。通过使用FT-IR，UV-Vis和（1）H NMR光谱法以及元素分析对染料进行了表征。已经通过循环伏安法在DMSO中以五种不同的扫描速率研究了染料的电化学行为。还已经在四种具有不同极性的有机溶剂中研究了染料的溶剂变色行为。此外，在密度泛函理论（DFT）的水平上，通过量规独立原子轨道（GIAO）方法研究了染料的（1）H化学屏蔽。
• Synthesis, anticancer evaluation, and docking studies of some novel azo chromene derivatives
  作者：Kaliyan Bhuvaneswari、Paramasivam Sivaguru、Appaswami Lalitha

  DOI：10.1002/jccs.201900481

  日期：2020.10

  We have described a simple, convenient, and high‐yielding one‐pot synthesis of novel azo chromene derivatives via a three‐component reaction of various azo aldehydes with dimedone and malononitrile using 10 mol% of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as catalyst and ethanol as solvent at reflux condition. All the synthesized compounds have been characterized using Fourier‐transform infrared spectroscopy

  我们已经描述了使用10 mol％的1,8-二氮杂双环[3.4.0]通过各种偶氮醛与二甲酮和丙二腈的三组分反应，简单，方便且高收率的新型偶氮苯二烯衍生物的一锅法合成[5.4.0]在回流条件下，十一碳烯（DBU）作为催化剂，乙醇作为溶剂。所有合成的化合物均使用傅里叶变换红外光谱（FT-IR），1 H NMR，13 C NMR和HR-MS光谱进行了表征，并进行了分子对接以探索人类胎盘芳香化酶细胞色素P450和环氧合酶的新型抑制剂。 2种酶。在所有对接的化合物中，化合物（E）-2-氨基-4-（4,4-二甲基-2,6-二氧代环己基）-6-（（3-甲氧基苯基）二氮烯基4 H-色烯-3-腈（4度）与抑制因子（Ki）为1.66 nM的人胎盘芳香化酶细胞色素P450酶（PDB：3EQM）的活性位点具有良好的结合亲和力，化合物4o也与环氧合酶2酶的活性位点（PDB：6COX）具有良好的结合力抑制常数（Ki）为367
• Facile and Mild Synthesis and Characterization of Some New Diazo Dyes on the Basis of Schiff Bases in the Presence of Nanocrystalline Magnesium Oxide as a Base Catalyst under Solvent-free Conditions
  作者：Hossein Naeimi、Zahra Rashid、Khadijeh Rabiei

  DOI：10.1002/jccs.201500264

  日期：2015.11

  In this research, some new diazo dyes including Schiff base have been synthesized by the condensation reaction between ethylenediamine and derivatives of salicylaldehyde containing diazo functional groups in the presence of nanocrystalline magnesium oxide as a solid base catalyst under solvent‐free conditions. Nanocrystalline magnesium oxide has been characterized by XRD, BJH and TEM techniques. The

  在这项研究中，在无溶剂条件下，通过以纳米二氧化镁作为固体碱催化剂存在下，乙二胺与含有重氮官能团的水杨醛衍生物的缩合反应，合成了一些新的重氮染料，包括席夫碱。纳米晶体氧化镁已经通过XRD，BJH和TEM技术进行了表征。以优异的产率和高纯度获得了相应的产物。所有获得的重氮-席夫碱都是高度着色的，可以用作有用的重氮染料，并通过光谱数据进行表征。
• Novel synthesized azo-benzylidene-thiourea as dual naked-eye chemosensor for selective detection of Hg2+ and CN¯ ions
  作者：Hamide Hosseinjani-Pirdehi、Nosrat O. Mahmoodi、Meysam Pasandideh Nadamani、Amir Taheri

  DOI：10.1016/j.jphotochem.2020.112365

  日期：2020.3

  Seven novel chemosensors contain azo chromophore and phenylthiourea, were synthesized and applied as colorimetric probes in aqueous solutions of dimethyl sulfoxide. The anion recognition studies exhibited that the synthesized azo dye derivatives act as a highly dual-sensitive and selective chromogenic sensor for naked-eye detection of Hg2+ and CN¯ ions, with a different color change from yellow to

  合成了七个包含偶氮发色团和苯硫脲的新型化学传感器，并将其用作比色探针在二甲基亚砜水溶液中的比色探针。所表现出的阴离子识别的研究，所合成的偶氮色素衍生物充当用于裸眼检测Hg的高度双灵敏的和选择性的显色传感器2+和CN ¯离子，具有从黄色到无色和黄色到红色不同的颜色变化，分别。检测（LOD）的限制，发现为图3c朝向汞2+和CN ¯离子分别为4.89μM和2.23μM。乔布图的结果表明化合物3c与Hg 2+的化学计量结合比为1：1和CN ¯为1：2。这些结果通过1 H NMR滴定实验证实。