1-(benzyl)-3-cyano-4,6-dimethylpyrid-2-one | 64488-19-3

• 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: 1-(benzyl)-3-cyano-4,6-dimethylpyrid-2-one
• 英文别名: 1-Benzyl-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile；1-benzyl-4,6-dimethyl-2-oxopyridine-3-carbonitrile
• CAS: 64488-19-3
• 化学式: C₁₅H₁₄N₂O
• mdl: MFCD00221300
• 分子量: 238.289
• InChiKey: JVGJGMSMIXKPPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzyl)-3-cyano-4,6-dimethylpyrid-2-one 在 硫酸 作用下， 以 水 为溶剂， 生成 1-(benzyl)-3-carboxy-4,6-dimethylpyrid-2-one
  参考文献：
  名称：

  Derivatives of 3-carboxy pyrid-2-ones

  摘要：

  属于1-取代苄基吡啶-2-酮-4,6-二烷基和4,5,6-三取代-3-羧酸、酰胺、酯和生理可接受盐类类别的新化合物。这些化合物具有生物活性，特别是作为配子杀虫剂和植物生长调节剂。还披露了新型的1-取代苄基-3-氰基-4,5,6-三取代吡啶-2-酮作为中间体。

  公开号：

  US04028084A1
• 作为产物：
  描述：

  2-氰基-N-(苯基甲基)-乙酰胺 、 乙酰丙酮 在 1,1,3,3-tetramethylguanidinium lactate 作用下， 生成 1-(benzyl)-3-cyano-4,6-dimethylpyrid-2-one
  参考文献：
  名称：

  Ionic Liquid Catalyzed 4,6-Disubstituted-3-Cyano-2-Pyridone Synthesis Under Solvent-Free Conditions

  摘要：

  A green protocol for the synthesis of 4,6-disubstituted-3-cyano-2-pyridones from cyanoacetamides and 1,3-dicarbonyl compounds or chalcones using guanidine based ionic liquid as catalyst has been developed. In solvent-free conditions at 30 A degrees C, [TMG][Lac] (1,1,3,3-tetramethylguanidine lactate) was found to have the highest catalytic activity among the ionic liquids including [TMG][Ac] (1,1,3,3-tetramethylguanidine acetate), [TMG][Pr] (1,1,3,3-tetramethylguanidine propionate), [TMG][n-Bu] (1,1,3,3-tetramethylguanidine n-butyrate) and [TMG][TFA] (1,1,3,3-tetramethylguanidine trifluoroacetate). The catalyst was recovered and recycled several times without significant loss of catalytic activity.

  DOI：

  10.1007/s10562-011-0700-5

文献信息

• Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems
  作者：Qifan Zhou、Fangyu Du、Xinjie Liang、Wenqiang Liu、Ting Fang、Guoliang Chen

  DOI：10.3390/molecules23071784

  日期：——

  system of ZnO, ZnCl2 and N,N-diisopropylethylamine (DIEA), that is highly effective for selective O-benzylation of 2-oxo-1,2-dihydropyridines using abundant substituted benzyl halides and related substituted 2-oxo-1,2-dihydropyridines compounds. This process allows access to a variety of O-benzyl products under mild reaction conditions, which are important synthetic intermediates in the protection of

  2-oxo-1,2-dihydropyridines 的选择性 O-苄基化在天然产物和生物活性分子的有机合成中起着关键作用。在此，我们报告了一种新型的 ZnO、ZnCl2 和 N,N-二异丙基乙胺 (DIEA) 的三元体系，该体系对于使用大量取代的苄基卤化物和相关取代的 2- 2-氧代-1,2-二氢吡啶的选择性 O-苄基化非常有效。氧代-1,2-二氢吡啶类化合物。该过程允许在温和的反应条件下获得各种 O-苄基产物，它们是保护官能团的重要合成中间体，代表了一种开发 2-oxo-1,2 的 O-苄基化的新方法-二氢吡啶。
• US4028084A
  申请人：——

  公开号：US4028084A

  公开（公告）日：1977-06-07
• US4104273A
  申请人：——

  公开号：US4104273A

  公开（公告）日：1978-08-01
• 10.1002/cplu.202400172
  作者：Salamanca-Perdigón, Kevin、Hurtado-Rodríguez, Diana、Portilla, Jaime、Iriepa, Isabel、Rojas, Hugo、Becerra, Diana、Castillo, Juan-Carlos

  DOI：10.1002/cplu.202400172

  日期：——

  Herein, a Cs2CO3‐promoted N‐alkylation of 3‐cyano‐2(1H)‐pyridones containing alkyl groups with diverse alkyl halides to synthesize N‐alkyl‐2‐pyridones over O‐alkylpyridines is reported. Alkyl dihalides resulted in complex mixtures of N‐ and O‐alkylated products. The primary factor influencing regioselectivity in these reactions is the electronic effects of substituents on the 2(1H)‐pyridone ring, as evidenced by the preferential formation of O‐alkylpyridines upon the introduction of aryl groups. Remarkably, we efficiently employed CuAAC and Ti(Oi‐Pr)4‐catalyzed amidation reactions to functionalize N‐alkyl‐2‐pyridones containing propargyl and ester groups, leading to the synthesis of 1,2,3‐triazoles and amides, respectively. Moreover, O‐alkylpyridines 10b and 10d displayed remarkable selectivity toward the A‐498 renal cancer cell line with growth inhibition percentages (%GI) of 54.75 and 67.64, respectively. The binding modes of compounds 10b and 10d to the PIM‐1 kinase enzyme were determined through molecular docking studies.
• Ionic Liquid Catalyzed 4,6-Disubstituted-3-Cyano-2-Pyridone Synthesis Under Solvent-Free Conditions
  作者：Sunil S. Chavan、Mariam S. Degani

  DOI：10.1007/s10562-011-0700-5

  日期：2011.11

  A green protocol for the synthesis of 4,6-disubstituted-3-cyano-2-pyridones from cyanoacetamides and 1,3-dicarbonyl compounds or chalcones using guanidine based ionic liquid as catalyst has been developed. In solvent-free conditions at 30 A degrees C, [TMG][Lac] (1,1,3,3-tetramethylguanidine lactate) was found to have the highest catalytic activity among the ionic liquids including [TMG][Ac] (1,1,3,3-tetramethylguanidine acetate), [TMG][Pr] (1,1,3,3-tetramethylguanidine propionate), [TMG][n-Bu] (1,1,3,3-tetramethylguanidine n-butyrate) and [TMG][TFA] (1,1,3,3-tetramethylguanidine trifluoroacetate). The catalyst was recovered and recycled several times without significant loss of catalytic activity.