5-(2,4-dihydroxybenzoyl)-1-(2-methoxyphenyl)pyridin-2(1H)-one | 1388221-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2,4-dihydroxybenzoyl)-1-(2-methoxyphenyl)pyridin-2(1H)-one
• 英文别名: 5-(2,4-Dihydroxybenzoyl)-1-(2-methoxyphenyl)pyridin-2-one；5-(2,4-dihydroxybenzoyl)-1-(2-methoxyphenyl)pyridin-2-one
• CAS: 1388221-12-2
• 化学式: C₁₉H₁₅NO₅
• 分子量: 337.332
• InChiKey: ZJBYFSPNVLXJSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-methyl 3-(7-hydroxy-4-oxo-4H-chromen-3-yl)acrylate 、 邻甲氧基苯胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以68%的产率得到5-(2,4-dihydroxybenzoyl)-1-(2-methoxyphenyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Re-cyclization of 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate with amines and their potential mechanism

  摘要：

  The synthesis of 2-pyridone derivatives from different substituted amines and various 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate derivatives was proposed and described. The optimized reaction conditions and the generality of the reaction were investigated, respectively. Moreover, less side products could be formed than the traditional method. Finally, based on the fact that (E)-methyl 2-(7-methoxy-4-oxo-3-((phenylamino)methylene)chroman-2-yl)acetate was separated and determined via X-ray single crystal diffraction, we could propose an interesting and reasonable reaction mechanism for the first time. The reaction could render this method particularly attractive for the efficient preparation of biologically and medicinally interesting molecules. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.032

文献信息

• Re-cyclization of 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate with amines and their potential mechanism
  作者：Yikai Zhang、Zhiliang Lv、Mingfeng Zhang、Ke Li

  DOI：10.1016/j.tet.2013.08.032

  日期：2013.10

  The synthesis of 2-pyridone derivatives from different substituted amines and various 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate derivatives was proposed and described. The optimized reaction conditions and the generality of the reaction were investigated, respectively. Moreover, less side products could be formed than the traditional method. Finally, based on the fact that (E)-methyl 2-(7-methoxy-4-oxo-3-((phenylamino)methylene)chroman-2-yl)acetate was separated and determined via X-ray single crystal diffraction, we could propose an interesting and reasonable reaction mechanism for the first time. The reaction could render this method particularly attractive for the efficient preparation of biologically and medicinally interesting molecules. (c) 2013 Elsevier Ltd. All rights reserved.