methyl 4-(3-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate | 1394014-79-9

• 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: methyl 4-(3-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate
• CAS: 1394014-79-9
• 化学式: C₁₄H₁₂ClNO₃
• 分子量: 277.707
• InChiKey: SSFNTWGSWYZYBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(3-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 4-(3-chlorophenyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid
  参考文献：
  名称：

  Diversity-Oriented Synthesis of 1-Substituted 4-Aryl-6-oxo-1,6-dihydropyridine-3-carboxamides.

  摘要：

  A simple five-step diversity-oriented synthesis of 1-substituted 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxamides was developed. Treatment of dimethyl 2-((dimethylamino)methylidene)-3-oxopentanedioate with twenty primary amines gave 1-substituted methyl 4-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylates. Transformation into the corresponding 4-tosyloxy and 4-chloro derivatives, followed by Suzuki-Miyaura arylations gave a series of eleven N-substituted methyl 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxylates. Combinatorial screening was employed to establish suitable reaction conditions for Suzuki-Miyaura arylation of N-alkylpyridones. Hydrolysis of the esters followed by parallel solution-phase amidation of the corresponding carboxylic acids with primary and secondary amines furnished a library of seventeen final products.

  DOI：

  10.1021/co3000709
• 作为产物：
  描述：

  dimethyl 2-(methylaminomethylidene)-3-oxopentanedioate 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 bis(η3-allyl-μ-chloropalladium(II)) 、 caesium carbonate 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-(3-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Diversity-Oriented Synthesis of 1-Substituted 4-Aryl-6-oxo-1,6-dihydropyridine-3-carboxamides.

  摘要：

  A simple five-step diversity-oriented synthesis of 1-substituted 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxamides was developed. Treatment of dimethyl 2-((dimethylamino)methylidene)-3-oxopentanedioate with twenty primary amines gave 1-substituted methyl 4-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylates. Transformation into the corresponding 4-tosyloxy and 4-chloro derivatives, followed by Suzuki-Miyaura arylations gave a series of eleven N-substituted methyl 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxylates. Combinatorial screening was employed to establish suitable reaction conditions for Suzuki-Miyaura arylation of N-alkylpyridones. Hydrolysis of the esters followed by parallel solution-phase amidation of the corresponding carboxylic acids with primary and secondary amines furnished a library of seventeen final products.

  DOI：

  10.1021/co3000709