5-phenylazo-4,6-dimethyl-3-cyano-2-pyridone | 147675-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-phenylazo-4,6-dimethyl-3-cyano-2-pyridone
• 英文别名: 4,6-dimethyl-2-oxo-5-(phenyldiazenyl)-1,2-dihydropyridine-3-carbonitrile；3-cyano-4,6-dimethyl-5-(phenyldiazenyl)-2-pyridone；4,6-Dimethyl-2-oxo-5-(2-phenylhydrazinylidene)-2,5-dihydropyridine-3-carbonitrile；4,6-dimethyl-2-oxo-5-phenyldiazenyl-1H-pyridine-3-carbonitrile
• CAS: 147675-03-4
• 化学式: C₁₄H₁₂N₄O
• 分子量: 252.275
• InChiKey: NAZSGKKZTJGELQ-UHFFFAOYSA-N

物化性质

• 熔点：
  285 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  387.6±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-phenylazo-4,6-dimethyl-3-cyano-2-pyridone 在 硫酸氢铵 、 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 3-cyano-4,6-dimethyl-2-(2'',3'',4''-tri-O-acetyl-β-D-arabinopyranosyloxy)-5-phenylazopyridine
  参考文献：
  名称：

  一些新型 2(1H)-吡啶酮阿拉伯糖苷的快速高效微波合成方法

  摘要：

  摘要 合成了两个系列的新型 3-cyano-2-(2'',3'',4''-tri-O-acetyl-β-D-arabinopyranosyloxy)pyridones 5a-h 和 9a,b。通过 2(1H)-吡啶酮或其盐与活化的阿拉伯糖反应，微波辐射已被用于在较温和的条件下以高产率获得这些产品。使用甲硅烷基方法获得相同的核苷 5a-h 和 9a,b。三乙胺用于从糖部分去除乙酰基保护基团，并以 85-91% 的产率产生游离核苷 6a-h 和 10a,b。

  DOI：

  10.1515/hc-2012-0091
• 作为产物：
  描述：

  pentane-2,3,4-trione 3-phenylhydrazone 在 sodium hydroxide 、 sodium ethanolate 、 氯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 8.0h， 生成 5-phenylazo-4,6-dimethyl-3-cyano-2-pyridone
  参考文献：
  名称：

  (氰基)硫代乙酰胺与β-二酮芳基腙的反应：2(1H)-吡啶硫酮、噻吩并[2,3-b]吡啶和吡唑并[3,4-b]吡啶的新合成

  摘要：

  描述了使用 (氰基) 硫代乙酰胺和 1,3-二酮的芳基腙作为起始组分的 2 (1 H)-吡啶硫酮、噻吩并 [2,3-b] 吡啶和吡唑并 [3,4-b] 吡啶的新型合成方法。

  DOI：

  10.1246/bcsj.66.555

文献信息

• Green Synthetic Approach and Antimicrobial Evaluation for Some Novel Pyridyl Benzoate Derivatives
  作者：H. A. Eldeab

  DOI：10.1134/s1070428019070200

  日期：2019.7

  4-chlorobenzoates have been synthesized by microwave-assisted condensation of the corresponding 2-oxo-1,2-dihydropyridine-3-carbonitriles with 4-chlorobenzoyl chloride under solvent-free conditions. Alternatively, some compounds have also been prepared by conventional heating in methylene chloride in the presence of triethylamine. The structure of the synthesized compounds has been confirmed by spectral data (FTIR

  在无溶剂的条件下，通过微波辅助缩合相应的2-oxo-1,2-二氢吡啶-3-腈与4-氯苯甲酰氯，合成了两个系列的4-氯苯甲酸吡啶基酯。或者，还通过在三乙胺存在下在二氯甲烷中常规加热来制备一些化合物。合成化合物的结构已通过光谱数据（FTIR，1D和2D NMR）证实。评价了新的苯甲酸吡啶基酯对革兰氏阴性和革兰氏阳性细菌的抗菌活性。3-氰基-5-[（4-羟基苯基）二氮烯基] -4-甲基-6-苯基吡啶-2-基4-氯苯甲酸酯对革兰氏阳性细菌（枯草芽孢杆菌和金黄色葡萄球菌）的活性）与用作标准抗生素的丁胺卡那霉素相当。
• Synthesis, Characterization, and Anticancer Activity (MCF-7) of Some Acetanilide-based Heterocycles
  作者：Ehab Abdel-Latif、Eman M. Keshk、Abdel-Galil M. Khalil、Ali Saeed、Heba M. Metwally

  DOI：10.1002/jhet.3294

  日期：2018.10

  A series of some novel 4‐(N‐substituted amino)‐acetanilide scaffolds was synthesized through the nucleophilic substitution reactions of the highly versatile N‐(4‐acetamidophenyl)‐2‐chloroacetamide (3) with various types of nucleophilic reagents such as benzothiazole‐2‐thiol, ethyl 2‐mercaptoacetate, 4,6‐dimethyl‐2‐mercapto‐nicotinonitrile, various thiocarbamoyl derivatives, ammonium thiocyanate, 3‐cyano‐4

  通过高度通用的N-（4-乙酰氨基苯基）-2-氯乙酰胺（3）与各种类型的亲核试剂（例如苯并噻唑）的亲核取代反应合成了一系列新颖的4-（N-取代氨基）-乙酰胺基支架-2-硫醇，2-巯基乙酸乙酯，4,6-二甲基-2-巯基烟腈，各种硫代氨基甲酰基衍生物，硫氰酸铵，3-氰基-4,6-二甲基-5-芳基偶氮吡啶-2-酮和丙二腈。合成的4-（N-取代氨基）乙酰苯胺支架通过光谱分析进行表征，并在体外测定其乳腺癌的抗癌活性。2-（4-乙酰胺基苯基氨基羰基）-3-氨基噻吩11，图13a和13b显示最高的细胞毒性活性。
• Synthesis and reactions of 3-cyano-4,6-dimethyl-2-pyridone
  作者：Abdel-Zaher A. Elassar

  DOI：10.1002/jhet.545

  日期：2011.3

  AbstractRapid synthesis of 3‐cyano‐4,6‐dimethyl‐2‐pyridone 3, using piprazine as a catalyst was reported. X‐ray data of the 4,6‐dimethyl‐2‐oxo‐1,2‐dihydropyridine‐3‐carbonitrile exhibited its oxo form. Synthesis of isoquinolinecarbonitrile and pyridylpyridazine using compound 3 was investigated. Reactivity of the synthesized pyridone toward different organic reagents was also studied. J. Heterocyclic Chem., (2011).
• The microwave-assisted synthesis of 5-arylazo-4,6-disubstituted-3-cyano-2-pyridone dyes
  作者：Dušan Z. Mijin、Mostafa Baghbanzadeh、Claudia Reidlinger、C. Oliver Kappe

  DOI：10.1016/j.dyepig.2009.10.006

  日期：2010.4

  A novel protocol for the rapid synthesis of pyridone colorants under controlled microwave irradiation ill a dedicated reactor is described. Short reaction times, high isolated yields. and versatility for different substrates are the advantages of the reported method. (C) 2009 Elsevier Ltd. All rights reserved.
• Antimicrobial Evaluation of New Synthesized Pyridine Nucleosides Under Solvent-Free Conditions
  作者：Nora M. Rateb、Hany A. El-Deab、Ibrahim M. Abdou

  DOI：10.1080/15257770.2013.827206

  日期：2013.9.2

  Two series of novel 3-cyano-2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxo) pyridines and 3-cyano-2-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyloxy)-4-trifluromethyl-6-phenyl pyridine were synthesized using efficient microwave methods. The targeted compounds were obtained in high yields by reacting 2-(1H)-pyridone or its salt with activated sugars using SiO2 under solvent-free conditions. Ammonolysis of the resulted acetylated nucleosides produced 3-cyano-2-(b beta-D-glucopyranosyloxo)-pyridines and 3-cyano-2-(beta-D-ribofuranosyloxy)-4-trifluoromethyl-6-phenyl pyridine. These new products were fully characterized using 1D and 2D NMR. These compounds were screened for their antibacterial activities against G(+) and G(-) bacteria and some found to exhibit better antibacterial activities than the control drug.