4-(4-nitrophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile | 888281-83-2

• 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-nitrophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 4-(4-nitrophenyl)-2-oxo-6-phenyl-1H-pyridine-3-carbonitrile
• CAS: 888281-83-2
• 化学式: C₁₈H₁₁N₃O₃
• 分子量: 317.304
• InChiKey: SUTCGGBRHYRJQD-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：

  乙基 2-氰基-3-(4-硝基苯基)丙烯酸酯 、 苯乙酮 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.03h， 以23%的产率得到4-(4-nitrophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  A microwave approach to the synthesis of certain 4-substituted phenyl-6-phenyl-3-cyano-2-pyridones

  摘要：

  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。

  DOI：

  10.2298/jsc130718145m

文献信息

• Synthesis of new substituted pyridine derivatives as potent anti-liver cancer agents through apoptosis induction: In vitro, in vivo, and in silico integrated approaches
  作者：Ahmed T.A. Boraei、Elsayed H. Eltamany、Ibrahim A.I. Ali、Sara M. Gebriel、Mohamed S. Nafie

  DOI：10.1016/j.bioorg.2021.104877

  日期：2021.6

  Liver cancer is the most common type of cancer in many countries. New studies and statistics show rising liver cancer worldwide, so it is essential to seek new agents for this type of cancer. PIM1 has an attractive target in the discovery of cancer medications as it is very much expressed in a variety of malignancies and influences such as tumorigenesis, cell cycle progression, cellular proliferation

  肝癌是许多国家最常见的癌症类型。新的研究和统计数据显示，全球肝癌呈上升趋势，因此寻找治疗此类癌症的新药物至关重要。PIM1 在癌症药物的发现中具有吸引人的目标，因为它在多种恶性肿瘤和影响（例如肿瘤发生、细胞周期进程、细胞增殖、细胞凋亡和细胞迁移）中大量表达。因此，合成了一系列吡啶酮和吡啶-酰胺并测试了抗肝癌活性。 在合成策略中，4,6-二芳基-3-氰基-2-吡啶酮3a-n使用一锅四组分合成方法合成。对 4,6-diphenyl-3-cayno-2-pyridone 3a进行结构修饰以增强活性。在K 2 CO 3存在下烷基化得到O-烷基化产物4-6。合成乙酰氧基酰肼7并环化成 1,3,4-恶二唑硫酮8，后者在硫上烷基化得到10。采用叠氮偶联法将2-(吡啶-2-基氧基)乙酰肼7与不同的胺和氨基酸酯偶联得到产物12a-e和13a-b。将合成的衍生物进行对HepG2和THLE-2细胞，细胞毒性化合
• 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。
• One-Pot Four Component Synthesis of 4, 6-Disubstituted 3-Cyano-2- Pyridones in Polyethylene Glycol
  作者：Santosh V. Nalage、Ajay P. Nikum、Mohan B. Kalyankar、Vijay S. Patil、Umesh D. Patil、Kamlesh R. Desale、Shamkant L. Patil、Sidhanath V. Bhosale

  DOI：10.2174/157017810791514832

  日期：2010.7.1

  The reaction of ketone, aldehyde, ethyl cyanoacetate and ammonium acetate in polyethylene glycol-600 is reported. The reaction proceeds smoothly in the absence of catalyst to yield 2-Pyridones.

  报告了酮、醛、氰乙酸乙酯和乙酸铵在聚乙二醇-600 中的反应。在没有催化剂的情况下，反应顺利进行，生成 2-吡啶酮。
• An efficient and facile multicomponent synthesis of 4,6-diarylpyridine derivatives under solvent-free conditions
  作者：Hassan A. El-Sayed、Nabil H. Ouf、Ahmed H. Moustafa

  DOI：10.1007/s11164-012-0972-4

  日期：2014.1

  We present an efficient and facile synthesis of 4,6-diaryl-2-oxo-1,2-dihydropyridine-3-carbonitriles (5a–j) via a four-component system of aromatic aldehydes (1), acetophenones (2), ethyl cyanoacetate (3), and ammonium acetate (4). The short reaction time coupled with the simplicity of the reaction procedure and clean reaction make this method one of the most efficient methods for synthesis of this class of compounds.

  我们介绍了一种通过芳香醛（1）、苯乙酮（2）、氰乙酸乙酯（3）和乙酸铵（4）四组分体系高效简便地合成 4,6-二芳基-2-氧代-1,2-二氢吡啶-3-甲腈（5a-j）的方法。该方法反应时间短、反应过程简单、反应清洁，是合成这类化合物最有效的方法之一。
• Synthesis and spectroscopic properties of pyridones — Experimental and theoretical insight
  作者：M. Nawaz、S. Hisaindee、J.P. Graham、M.A. Rauf、N. Saleh

  DOI：10.1016/j.molliq.2013.12.033

  日期：2014.5

  Cyano pyridone (CPy) and its substituted derivatives -OCH3 and -NO2) were synthesized and their absorption spectra were examined in different solvents. The absorption spectra of CPy in different solvents indicated a dependence on the polarizability of the solvent. NMR studies of the keto and enol equilibrium in CPy revealed temperature dependence, with the keto form being more predominant. The equilibrium constant values were in agreement with the theoretical calculations. The calculated pK(a), value for CPy was found to be 9.50 +/- 0.57, whereas, for the nitro and methoxy substituted CPy, the values were 8.52 +/- 0.36 and 11.04 +/- 0.21 respectively. In mixed solvent systems, the preferential solvation was observed in DMSO/CH2Cl2 mixtures, whereas in DMSO/i-PrOH, the mixture behaved ideally. The calculations using the PCM model indicated Delta G degrees values favoring the keto form in both dichloromethane and DMSO. The calculated transition energies were found to be higher than those observed experimentally. For each compound, the keto form was predicted to absorb at a lower energy than the enol form. The main transition of both forms of CPy corresponded to a pi-pi* transition from the HOMO -> LUMO of the compound. (C) 2013 Elsevier B.V. All rights reserved.