3-cyano-4-(2-nitrophenyl)-6-phenyl-2(1H)-pyridone | 910134-41-7

• 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: 3-cyano-4-(2-nitrophenyl)-6-phenyl-2(1H)-pyridone
• 英文别名: 4-(2-nitrophenyl)-2-oxo-6-phenyl-1H-pyridine-3-carbonitrile
• CAS: 910134-41-7
• 化学式: C₁₈H₁₁N₃O₃
• 分子量: 317.304
• InChiKey: UPYQOBKTCOTPAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻硝基苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.02h， 生成 3-cyano-4-(2-nitrophenyl)-6-phenyl-2(1H)-pyridone
  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

• A microwave approach to the synthesis of certain 4-substituted phenyl-6-phenyl-3-cyano-2-pyridones
  作者：Aleksandar Marinkovic、Dusan Mijin、Jelena Mirkovic、Veselin Maslak、Oliver Kappe

  DOI：10.2298/jsc130718145m

  日期：——

  A study of the synthesis of 4-substituted phenyl-6-phenyl-3-cyano-2-pyridones from 2-cyano-3-phenylsubstituted acrylates and acetophenone is presented. 2-Pyridones were obtained using conventional as well as microwave synthesis using solvent and solvent free reactions in domestic and lab microwave ovens. The structure of the obtained pyridones was confirmed by m.p., FT-IR, NMR and UV data.

  研究了从 2-氰基-3-苯基取代丙烯酸酯和苯乙酮合成 4-取代苯基-6-苯基-3-氰基-2-吡啶酮的过程。 和苯乙酮合成 4-取代苯基-6-苯基-3-氰基-2-吡啶酮的研究。 通过传统和微波合成法，利用溶剂和无溶剂反应，获得了 2-吡啶酮 在家用和实验室微波炉中使用溶剂和无溶剂反应，获得了 2-吡啶酮。 所得吡啶酮的结构通过 m.p.、傅立叶变换红外光谱、核磁共振和 紫外数据证实了所获吡啶酮的结构。
• Synthesis and biological screening of some pyridine derivatives as anti-malarial agents
  作者：Adnan A. Bekhit、Ariaya Hymete、Ashenafi Damtew、Abdel Maaboud I. Mohamed、Alaa El-Din A. Bekhit

  DOI：10.3109/14756366.2011.575071

  日期：2012.2.1

  Two series of pyridine derivatives were synthesised and evaluated for their in vivo anti-malarial activity against Plasmodium berghei. The anti-malarial activity was determined in vivo by applying 4-day standard suppressive test using chloroquine (CQ)-sensitive P. berghei ANKA strain-infected mice. Compounds 2a, 2g and 2h showed inhibition of the parasite multiplication by 90, 91 and 80%, respectively, at a dose level of 50 mu mol/kg. Moreover, The most active compounds (2a, 2g and 2h) were tested in vitro against CQ-resistant Plasmodium falciparum RKL9 strains where compound 2g showed promising activity with IC50 = 0.0402 mu M. The compounds were non-toxic at 300 and 100 mg/kg through the oral and parenteral routes, respectively. The docking pose of the most active compounds (2a, 2g and 2h) in the active site of dihydrofolate reductase enzyme revealed several hydrogen and hydrophobic interactions that contribute to the observed anti-malarial activities.
• 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。