methyl 4-hydroxy-1-(4-methoxyphenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate | 1394014-53-9

• 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-hydroxy-1-(4-methoxyphenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate
• CAS: 1394014-53-9
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: VNCOYVICEZHWMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.76
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxy-1-(4-methoxyphenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate 以 丙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 methyl 1-(4-methoxyphenyl)-4,6-dioxo-5-((2-phenylhydrazinyl)methylene)-1,4,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis of 1,5-disubstituted-4-oxo-4,5-dihydro-1 H -pyrazolo[4,3- c ]pyridine-7-carboxamides

  摘要：

  1,5-Disubstituted-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamides functionalized at positions 1, 5, and 7 were prepared in six straightforward steps from cheap, commercially available dialkyl acetone-1,3-dicarboxylate. Due to the instability of methyl 1-benzyl-substituted pyrazolo[4,3-c]pyridine-7-carboxylates under basic hydrolytic conditions (LiOH/H2O), a detour via the corresponding benzyl esters was introduced to deliver the final 1-benzyl-substituted-bicyclic carboxamides in seven steps. The designed synthetic route is suitable for the construction of a larger library of compounds. All the key compounds have been characterized by NMR spectroscopic techniques and X-ray analysis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.034
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 methyl 4-hydroxy-1-(4-methoxyphenyl)-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