1-phenyl-3-cyano-4-methyl-6-hydroxy-2-pyridone | 26294-00-8

• 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: 1-phenyl-3-cyano-4-methyl-6-hydroxy-2-pyridone
• 英文别名: 6-hydroxy-4-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonitrile；1-N-phenyl-4-methyl-3-cyano-6-hydroxy-2-pyridone；3-cyano-6-hydroxy-4-methyl-1-phenyl-2-pyridone；1-phenyl-3-cyano-4-methyl-6-hydroxypyrid-2-one；4-methyl-2,6-dioxo-1-phenyl-1,2,3,6-tetrahydro-pyridine-3-carbonitrile
• CAS: 26294-00-8
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: KYTZAAGGVBMEFO-UHFFFAOYSA-N

物化性质

• 沸点：
  367.6±42.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-氨基-2-苯并噻唑-2-苯酚 、 1-phenyl-3-cyano-4-methyl-6-hydroxy-2-pyridone 在 硫酸 、 sodium nitrite 、 sodium hydroxide 作用下， 反应 3.75h， 生成 5-((3-(benzo[d]thiazol-2-yl)-4-hydroxyphenyl)diazenyl)-6-hydroxy-4-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis, bioactivities, DFT and in-silico appraisal of azo clubbed benzothiazole derivatives

  摘要：

  Six new azo clubbed benzothiazole dyes were synthesized by diazotization reaction. These six novel compounds were characterized using H-1 NMR, FTIR, UV-Visible, fluorescence spectroscopy, LC-MS, and elemental analysis. The in-vitro antimicrobial screening studies were performed using popular REMA assay method on "gram-positive" ("Staphylococcus aureus") and "gram-negative" ("Escherichia coli") strains. DNA cleavage study was also carried out to check nuclease activity. The "HOMO-LUMO" theoretical calculations were correlated with current in-vitro antibacterial results. In -silico studies were performed using Molecular Docking, Molecular dynamics, Prime MMGBSA, admetSAR, and QikProp ADMET method. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.04.123
• 作为产物：
  描述：

  苯佐卡因 在 盐酸 作用下， 以 水 为溶剂， 生成 1-phenyl-3-cyano-4-methyl-6-hydroxy-2-pyridone
  参考文献：
  名称：

  Water-insoluble monoazo pyridine dyes

  摘要：

  将无水溶性的单偶氮染料的配方##SPC1##翻译成中文： 通过将苯、萘、二苯、二苯甲烷或异环系列的重氮化胺与适当的6-羟基-2-吡啶酮反应而制得，该染料用于合成织物的染色和印花，可呈现出从黄色到红色的色调，并具有优异的耐光和升华牢度。

  公开号：

  US03957749A1

文献信息

• Benzothiazole-pyridone and benzothiazole-pyrazole clubbed emissive azo dyes and dyeing application on polyester fabric: UPF, biological, photophysical and fastness properties with correlative computational assessments
  作者：Chaitannya W. Ghanavatkar、Virendra R. Mishra、Nagaiyan Sekar

  DOI：10.1016/j.saa.2020.118064

  日期：2020.4

  benzothiazole-pyridone and benzothiazole-pyrazole containing disperse azo dyes are reported. These heterocyclic azo dyes are decorated with 'separate ESIPT core' and show emission in seven solvents of different polarity. After application on polyester fabric, "very good to excellent" light and washing fastness properties were observed. Thermal stability of 'dyed fabric' was analysed by sublimation fastness test-

  据报道含有苯并噻唑-吡啶酮和苯并噻唑-吡唑的分散偶氮染料的位置异构体。这些杂环偶氮染料装饰有“独立的ESIPT核”，并在七种极性不同的溶剂中显示出光。在聚酯织物上施涂后，观察到“非常好至极好”的耐光性和耐洗牢度。通过升华牢度测试分析了“染色织物”的热稳定性，发现其在210°C时的“非常好”。四种“染色织物”的紫外线保护因子（UPF）分析表明，紫外线能够阻挡96-97％的紫外线。通过琼脂扩散法发现染料对革兰氏阳性和阴性细菌均有效，所有“染色的织物”也显示出金黄色葡萄球菌或钾的减少超过92％或94％。通过“ AATCC 100”方法分别获得肺炎。使用密度泛函理论（DFT）对染料的结构进行优化，以推导稳定的互变异构形式。然后将计算出的HOMO-LUMO缺口与抗菌活性进行比较。还比较了亲电性指数和耐光性，发现它们具有很好的相关性。
• Studies on heterocyclization of acetoacetanilide
  作者：Mohamed Sherif、Mohamed Assy、Nabil Yousif、Mohamed Galahom

  DOI：10.1007/s13738-012-0128-x

  日期：2013.2

  Base-induced cyclocondensation of acetoacetanilide (1) and benzoyl isothiocyanate (2) afforded mercaptopyridine (4). Compound 4 reacted with NaOCl in presence of NH4OH/NaOH to produce isothiazolopyridine (6). Heterocyclization of 4 by ethyl bromoacetate and/or phenacyl bromide afforded pyridothiazapene and pyridine derivatives 7, 8, respectively. The synthesis of pyrazolopyridine (9) was achieved by reaction of 4 with hydrazine hydrate. Oxidative cyclization of 4 by Br2 produced isothiazolopyridine (10). Chlorination of compound 4 yielded isothiazolopyridine dioxide (11). Compound 1 transformed into pyrane derivatives 12 and 13 by reaction with benzylidenemalononitrile and benzylideneacetophenone, respectively. Heterocyclization of compound 1 by ethylcyanoacetate and diethyloxalate afforded pyridine and cyclopentane derivatives 14 and 15, respectively. Compound 1 heterocyclized to indenopyrane (16) or indenopyrrole (17) upon reacted with ninhydrin on cold and hot condition, respectively. Heterocyclization of compound 1 and benzilmonohydrazone afforded pyridazine derivative 18. Coupling of 1 with diazonium salt afforded hydrazone 19 which cyclized using CS2/KOH gave pyridazine derivative 20.

  碱催化的环缩合反应将乙酰乙酸苯胺（1）与苯甲酰异硫氰酸酯（2）反应生成了巯基吡啶（4）。化合物4在氨水/氢氧化钠存在下与NaOCl反应，生成了异噻唑吡啶（6）。通过乙基溴乙酸酯和/或苯乙酮溴化物对4进行的杂环化反应分别得到了吡啶噻唑烯和吡啶衍生物7和8。通过将化合物4与水合肼反应，合成了吡唑吡啶（9）。化合物4与Br2的氧化环化反应生成了异噻唑吡啶（10）。化合物4的氯化反应生成了异噻唑吡啶二氧化物（11）。化合物1在与苯乙烯二氮烯腈和苯乙酮反应后转化为吡喃衍生物12和13。通过乙基氰乙酸酯和二乙氧基草酸酯对化合物1的杂环化反应分别得到了吡啶和环戊烷衍生物14和15。化合物1在冷却和加热条件下分别与蒽烯酮反应生成了印烯吡喃（16）或印烯吡咯（17）。化合物1与苯基单肼反应进行的杂环化反应生成了吡唑杂环衍生物18。化合物1与二氮阳离子盐的偶联反应生成了肼酮（19），而使用CS2/KOH使其环化得到吡唑衍生物20。
• 一种双偶氮分散染料及其制备方法和用途
  申请人：南京工业大学

  公开号：CN104629401B

  公开（公告）日：2017-03-29

  本发明涉及一种不合致癌诱变中间体的双偶氮分散染料及其制备方法和用途。所述的双偶氮分散染料如下结构所示：其中：R1、R2、R3、R4、R5分别为H、甲基、乙基、烷氧基、溴、氯、碘、丙基、异丙基、叔丁基、氨基、磺酸基或者氰基中的一种或者多种。通过如下方法制得：将3，3‑二氨基二苯砜或4，4‑二氨基二苯砜溶解于盐酸的水溶液中，滴加亚硝酸盐溶液进行重氮化，再与苯基吡啶酮类偶合组分在弱碱性条件下进行偶合。本发明制备得到的双偶氮分散染料用于涤纶及涤棉混纺织物的染色，具有良好的应用性能。
• Synthesis of 3-Cyano-6-hydroxy-5-[2-(perfluoroalkyl)phenylazo]-2-pyridones and Their Application for Dye Diffusion Thermal Transfer Printing
  作者：Masaki Matsui、Bharati Joglekar、Yoshinao Ishigure、Katsuyoshi Shibata、Hiroshige Muramatsu、Yuukichi Murata

  DOI：10.1246/bcsj.66.1790

  日期：1993.6

  New fluorine-containing azopyridone dyes, 3-cyano-6-hydroxy-5-[2-(perfluoroalkyl)phenylazo]-2-pyridones, have been synthesized. Though the introduction of a long perfluoroalkyl group lowered film forming ability and sensitivity, 5-[2-(trifluoromethyl)phenylazo]- and 5-[2-(perfluorobutyl)phenylazo]-3-cyano-4-methyl-6-hydroxy-2-pyridones showed good photostability.

  新的含氟偶氮吡啶酮染料--3-氰基-6-羟基-5-[2-（全氟烷基）苯基偶氮]-2-吡啶酮被合成出来。虽然长全氟烷基的引入降低了成膜能力和灵敏度，但 5-[2-（三氟甲基）苯基偶氮]- 和 5-[2-（全氟丁基）苯基偶氮]-3-氰基-4-甲基-6-羟基-2-吡啶酮显示出良好的光稳定性。
• Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study
  作者：Ismail Ajaj、Jasmina Markovski、Milica Rančić、Dušan Mijin、Miloš Milčić、Maja Jovanović、Aleksandar Marinković

  DOI：10.1016/j.saa.2015.05.055

  日期：2015.11

  time-dependent density functional (TD-DFT) method. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader’s analysis. Linear solvation energy relationships (LSER) rationalized solvent influence on tautomeric equilibrium. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter)

  2（6）-羟基-4-甲基-6（2）-氧-1-（取代的苯基）-1,2（1,6）-二氢吡啶-3-腈，2-PY的互变异构平衡状态/ 6-PY，使用实验和理论方法进行了评估。实验数据借助时变密度函数（TD-DFT）方法进行解释。通过使用分子中的原子量子理论（即）来获得电子电荷密度。贝德的分析。线性溶剂化能量关系（LSER）合理化了溶剂对互变异构平衡的影响。将线性自由能关系（LFER）应用于取代基诱导的NMR化学位移（SCS）使用SSP（单个取代基参数）和DSP（双取代基参数）模型。理论计算和获得的相关性使我们深入了解了分子构象对取代基电子效应的传递，不同的溶剂-溶质相互作用以及互变异构平衡状态的影响。