4-(4-fluorophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile | 919357-39-4

• 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: 4-(4-fluorophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 4-(4-Fluorophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile；4-(4-fluorophenyl)-2-oxo-6-phenyl-1H-pyridine-3-carbonitrile
• CAS: 919357-39-4
• 化学式: C₁₈H₁₁FN₂O
• 分子量: 290.297
• InChiKey: NIVMDXLANSIHQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 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：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 、 苯乙酮 、 丙二腈 在 sodium hydroxide 作用下， 反应 0.5h， 以83%的产率得到4-(4-fluorophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  在无溶剂条件下合成4,6-二芳基-2（1 H）-吡啶酮的有效简便方法

  摘要：

  据报道，在无溶剂条件下，在氢氧化钠存在下，通过芳族醛，芳族酮和丙二腈的一锅法反应，可以高效，方便地制备4,6-二芳基-2（1 H）-吡啶酮。该方法的优点是收率高，反应条件温和，后处理容易，试剂便宜且与现有方法相比环境友好。

  DOI：

  10.1002/jhet.5570440641

文献信息

• An Efficient and Facile Synthesis of 2-Amino-4,6-diarylbenzene-1,3-dicarbonitrile and 1,2-Dihydro-2-oxo-4,6-diarylpyridine-3-carbonitrile under Solvent-free Conditions
  作者：Liangce Rong、Xiaoyue Li、Haiying Wang、Daqing Shi、Shujiang Tu

  DOI：10.1246/cl.2006.1314

  日期：2006.11

  A one-pot three-component condensation of aromatic aldehyde, aromatic ketone, and malononitrile leading to an efficient synthesis of 2-amino-4,6-diarylbenzene-1,3-dicarbonitrile and 1,2-dihydro-2-oxo-4,6-diarylpyridine-3-carbonitrile has been carried out in a mortar just by grinding or heating under solvent-free conditions. Compared with the classical reaction conditions, these new synthetic methods have the advantages of excellent yields, shorter reaction time, and mild reaction conditions.

  一种一锅三组分冷凝反应方法，使用芳香醛、芳香酮和丙二腈，在研钵中通过简单的研磨或无溶剂条件下加热，实现了2-氨基-4,6-二芳基苯-1,3-二腈和1,2-二氢-2-氧-4,6-二芳基吡啶-3-腈的高效合成。与传统反应条件相比，这些新的合成方法具有优良的产率、更短的反应时间和温和的反应条件等优点。
• One‐Pot Synthesis of 4,6‐Diaryl‐2‐oxo‐1,2‐dihydropyridine‐3‐carbonitriles via Three‐Component Cyclocondensation under Solvent‐Free Conditions
  作者：Liangce Rong、Hongxia Han、Hong Jiang、Daqing Shi、Shujiang Tu

  DOI：10.1080/00397910701749682

  日期：2008.1

  Abstract An efficient and facile synthesis of 4,6‐diaryl‐2‐oxo‐1,2‐dihydropyridine‐3‐carbonitriles via three‐component cyclocondensation from aromatic aldehydes, aromatic ketones, and 2‐cyanoacetamide under solvent‐free conditions is described. The mild reaction conditions, simple protocol, and clean reaction make this protocol practical and economically attractive.

  摘要描述了在无溶剂条件下，通过芳香醛、芳香酮和 2-氰基乙酰胺的三组分环缩合反应，高效、简便地合成 4,6-二芳基-2-氧代-1,2-二氢吡啶-3-甲腈。温和的反应条件、简单的方案和干净的反应使该方案实用且具有经济吸引力。
• 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 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.
• An efficient and facile procedure for the synthesis of 4,6-diaryl-2(1H)-pyridones under solvent-free conditions
  作者：Liangce Rong、Haiying Wang、Jingwen Shi、Fang Yang、Hao Yao、Shuajiang Tu、Daqing Shi

  DOI：10.1002/jhet.5570440641

  日期：2007.11

  An efficient and convenient method for the preparation of 4,6-diaryl-2(1H)-pyridones by the one-pot reaction of aromatic aldehydes, aromatic ketones and malononitrile, in the presence of sodium hydroxide under solventfree condition is reported. This method has the advantages of good yields, mild reaction conditions, easy workup, inexpensive reagents and being environmentally friendly over the existing

  据报道，在无溶剂条件下，在氢氧化钠存在下，通过芳族醛，芳族酮和丙二腈的一锅法反应，可以高效，方便地制备4,6-二芳基-2（1 H）-吡啶酮。该方法的优点是收率高，反应条件温和，后处理容易，试剂便宜且与现有方法相比环境友好。