4-(4-chlorophenyl)-5,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile | 65429-80-3

• 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: 4-(4-chlorophenyl)-5,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 3-cyano-4-(4-chlorophenyl)-5,6-dimethyl-2(1H)-pyridone；4-(4-chloro-phenyl)-5,6-dimethyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile；4-(4-Chlorphenyl)-3-cyan-5,6-dimethyl-2-pyridon；4-(4-chlorophenyl)-5,6-dimethyl-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 65429-80-3
• 化学式: C₁₄H₁₁ClN₂O
• 分子量: 258.707
• InChiKey: VWIOHRLAJOYHRA-UHFFFAOYSA-N

物化性质

• 熔点：
  294-295 °C(Solv: ethanol (64-17-5))
• 沸点：
  436.0±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.01h， 生成 4-(4-chlorophenyl)-6-ethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 、 4-(4-chlorophenyl)-5,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  Cascade synthesis of 2-pyridones using acrylamides and ketones

  摘要：

  在微波辅助下，2-氰乙酰胺与芳香醛发生非催化缩合反应，并与丙烯酰胺发生由烯酸酯介导的迈克尔式加成反应，随后发生氧化环化反应，从而以良好至极佳的收率生成 2-吡啶酮。不对称酮会产生两种烯醇异构体，因此丁-2-酮和戊-2-酮的热力学和动力学产物已被分离出来并完全定性。

  DOI：

  10.1039/c4ra06619g

文献信息

• Efficient One-Pot Four-Component Synthesis and X-ray Crystallographic Structure of 2-Pyridone Derivatives
  作者：Saeed Balalaie、Mohammed M. Hashemi、S. Hadi Khezri、Frank Rominger、Elmira Ghabraie、Thomas Oeser

  DOI：10.1002/jhet.1632

  日期：2013.11

  A series of 3‐cyano‐2‐pyridone derivatives were synthesized by one‐pot four‐component condensation reaction involving a benzaldehyde derivative, alkyl cyanoacetate, acyclic or cyclic ketones, and ammonium acetate in reflux condition. The X‐ray structure of the products 5a and 5d confirm symmetric dimers via hydrogen bonding interactions between individual pyridine molecules showing, in addition, also

  通过一锅四组分缩合反应合成了一系列3-氰基-2-吡啶酮衍生物，该反应涉及苯甲醛衍生物，氰基乙酸烷基酯，无环或环状酮和乙酸铵在回流条件下。产物5a和5d的X射线结构通过单个吡啶分子之间的氢键相互作用证实了对称的二聚体，此外还显示了π-π堆积相互作用。
• Enzymatic multicomponent reaction for simultaneous synthesis of two important scaffolds, pyridin-2-ones and α-alkylated nitriles
  作者：Zhi-Qiang Liu、Yu-Jing Hu、Xiao-Yang Chen、Qi Wu、Xian-Fu Lin

  DOI：10.1016/j.tet.2014.12.021

  日期：2015.1

  An efficient approach for the synthesis of highly substituted pyridin-2-one derivatives and alpha-alkylated nitriles through enzymatic multicomponent reaction (MCR) was developed. This MCR involved biomimetic reduction between 3,4-dihydropyridin-2-one and activated olefin, both of which were in situ generated in the Acylase Amano (AA)-catalyzed domino reaction starting from benzaldehyde, cyanoacetamide and ketone. A wide range of substituted benzaldehydes and ketones were accepted by this reaction. Both final products (pyridin-2-one derivatives and alpha-alkylated nitriles) were important skeletons and synthetic intermediates. The synthetic application of prepared alpha-alkylated nitrile was demonstrated by converting it into the corresponding alpha-alkyl-beta(2)-amino acid with high yield. (C) 2014 Elsevier Ltd. All rights reserved.
• Cascade synthesis of 2-pyridones using acrylamides and ketones
  作者：Sunil K. Rai、Shaziya Khanam、Ranjana S. Khanna、Ashish K. Tewari

  DOI：10.1039/c4ra06619g

  日期：——

  Microwave assisted non-catalytic condensation of 2-cyanoacetamide with aromatic aldehydes, and enolate mediated Michael-type addition to acrylamide followed by oxidative cyclization, produce 2-pyridones in good to excellent yield. Unsymmetrical ketones produce two regioisomeric enolates, therefore thermodynamic and kinetic products of butan-2-one and pentan-2-one have been isolated and fully characterized.

  在微波辅助下，2-氰乙酰胺与芳香醛发生非催化缩合反应，并与丙烯酰胺发生由烯酸酯介导的迈克尔式加成反应，随后发生氧化环化反应，从而以良好至极佳的收率生成 2-吡啶酮。不对称酮会产生两种烯醇异构体，因此丁-2-酮和戊-2-酮的热力学和动力学产物已被分离出来并完全定性。