2-oxo-1,5-diphenyl-1,2-dihydropyridine-3-carbonitrile | 106719-01-1

• 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: 2-oxo-1,5-diphenyl-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 3-Cyano-1,5-diphenyl-2(1H)-pyridone；2-Oxo-1,5-diphenylpyridine-3-carbonitrile
• CAS: 106719-01-1
• 化学式: C₁₈H₁₂N₂O
• 分子量: 272.306
• InChiKey: QFULDWIISLCUIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  443.7±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙炔 、 5-Chloro-3-cyano-1-phenyl-2(1H)-pyrazinone 生成 2-oxo-1,5-diphenyl-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  TUTONDA, M.;VANDERZANDE, D.;VEKEMANS, J.;TOPPET, S.;HOORNAERT, G., TETRAHEDRON LETT., 1986, 27, N 22, 2509-2512

  摘要：

  DOI：

文献信息

• Generation of specifically substituted pyridines and pyridones from 2(1h) pyrazinones and acetylenes : A FMO description
  作者：M. Tutonda、D. Vanderzande、M. Hendrickx、G. Hoornaert

  DOI：10.1016/s0040-4020(01)87770-x

  日期：1990.1

  The title compounds were obtained from reaction of variously substituted 2(1H)pyrazinones with acetylenic derivatives. Experimental evidence points out to a two step mechanism : a Diels Alder cycloaddition followed by immediate decomposition of the adducts into the title products via two competitive retro Diels Alder reactions. The product distribution, which is shown to be highly dependent on the

  标题化合物获自各种取代的2（1H）吡嗪酮与炔属衍生物的反应。实验证据指出了两步机理：Diels Alder环加成反应，然后通过两个竞争性Diels Alder逆向反应将加合物立即分解为标题产物。一个简单的FMO模型可以说明产物分布高度依赖于反应物的取代模式。
• Diels-alder reactions of the heterodiene system in 2(1h)-pyrazinones
  作者：M. Tutonda、D. Vanderzande、J. Vekemans、S. Toppet、G. Hoornaert

  DOI：10.1016/s0040-4039(00)84570-0

  日期：1986.1

  acetylenic derivatives to give specifically substituted pyridones or pyridines. The observed selectivity can be explained in terms of HO-LU interactions for the reagents and two competitive retro Diels-Alder reactions of the primary bicycloadducts. With cyanotosylate as dienophile no pyrimidone derivative but a new 2(1H)-pyrazinone is obtained.

  各种取代的2（1H-吡嗪酮）与炔属衍生物反应生成特定取代的吡啶酮或吡啶。观察到的选择性可以通过试剂的HO-LU相互作用和一级双环加合物的两个竞争性Diels-Alder反应进行解释。作为双亲物，没有嘧啶酮衍生物，但是获得了新的2（1H）-吡嗪酮。
• One step synthesis of 1,5-diaryl pyridin-2(1H)-ones from 2-aryl vinamidinium salts and N-aryl cyanoacetamides
  作者：Jiabin Yang、Guoqiang Su、Yu Ren、Yang Chen

  DOI：10.1016/j.tet.2014.09.041

  日期：2014.11

  A one step, direct method for the synthesis of 1,5-diaryl pyridin-2(1H)-one derivatives by condensation of 2-aryl vinamidinium salts with N-aryl cyanoacetamides has been developed. This method can conveniently provide the corresponding 1,5-diaryl pyridin-2(1H)-one derivatives with various substituents in good yields and overcome the drawbacks of existing methods such as poor substrate scope, heavy metal pollution, and low yields. The formation mechanism of the products was illustrated. (C) 2014 Elsevier Ltd. All rights reserved.