4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester | 1174525-17-7

• 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-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester
• 英文别名: Methyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate；methyl 4-hydroxy-1-methyl-6-oxopyridine-3-carboxylate
• CAS: 1174525-17-7
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: SFMWGBBONPTXJY-UHFFFAOYSA-N

物化性质

• 沸点：
  301.9±42.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester 在 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 、 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 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester
  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

• Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy
  作者：Mingxuan Liang、Mengling He、Zhiqing Zhong、Bei Wan、Qingfeng Du、Shaoyu Mai

  DOI：10.1002/anie.202400741

  日期：2024.4.22

  A general and catalytic α-arylation of cyclic 1,3-dicarbonyls have been developed, providing expedient access toward a wide range of high-value 2-aryl (hetero)cyclic 1,3-dicarbonyls. The key to success is through a cyclic iodonium ylide strategy. Our approach is base-free and exhibits broad substrate scope (>100 examples). Importantly, our approach allows late-stage modification and significantly simplifying

  环状 1,3-二羰基的通用催化 α-芳基化已经开发出来，为获得各种高价值的 2-芳基（杂）环 1,3-二羰基提供了便利。成功的关键是通过环状碘叶立德策略。我们的方法是无碱基的，并且具有广泛的底物范围（> 100 个示例）。重要的是，我们的方法允许后期修改并显着简化先前的合成。