1-methyl-6-oxo-4-phenyl-1,6-dihydropyridine-3-carboxylic acid | 1394014-91-5

• 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-methyl-6-oxo-4-phenyl-1,6-dihydropyridine-3-carboxylic acid
• CAS: 1394014-91-5
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: ZVLJVMQINFJCBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methyl-6-oxo-4-phenyl-1,6-dihydropyridine-3-carboxylic acid 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 1-methyl-6-oxo-4-phenyl-N-(3-(pyrrolidin-1-yl)propyl)-1,6-dihydropyridine-3-carboxamide
  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-((dimethylamino)methylene)-3-oxopentanedioate 在 盐酸 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 bis(η3-allyl-μ-chloropalladium(II)) 、 水 、 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 1-methyl-6-oxo-4-phenyl-1,6-dihydropyridine-3-carboxylic 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

文献信息

• Diversity-Oriented Synthesis of 1-Substituted 4-Aryl-6-oxo-1,6-dihydropyridine-3-carboxamides.
  作者：Jernej Baškovč、Georg Dahmann、Amalija Golobič、Uroš Grošelj、Drago Kočar、Branko Stanovnik、Jurij Svete

  DOI：10.1021/co3000709

  日期：2012.9.10

  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.