2-(3-Methyl-quinoxalin-2-ylmethoxy)-benzoic acid methyl ester | 127173-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-Methyl-quinoxalin-2-ylmethoxy)-benzoic acid methyl ester
• 英文别名: Methyl 2-[(3-methylquinoxalin-2-yl)methoxy]benzoate
• CAS: 127173-15-3
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: JUACUZDAEZJGKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-Methyl-quinoxalin-2-ylmethoxy)-benzoic acid methyl ester 在 氢氧化钾 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.25h， 生成 2-(3-methyl-quinoxalin-2-ylmethoxy)-benzoic acid 3-methyl-quinoxalin-2-ylmethyl ester
  参考文献：
  名称：

  Quinoxalines. IX. Reaction of 2-(Halogenomethyl)-quinoxalines and -quinoline with hydroxybenzoic acids and their esters

  摘要：

  In the presence of a base the title compounds react to products with ether structure (4,6), or with ester structure (3), or to structure 5 containing both functionalities in dependence on the mole ratio of the starting substances, on reaction conditions and on the substituent patterns in the hydroxybenzoic acid component.Under the influence of alkali hydroxide the m- and p-substituted compounds (6e-g) are saponified to the alkali salts of the carboxylic acid (4b,c). The o-substituted compounds (6a-d), however, are cyclized to the benzo[b]furanylquinoxalines (8). 8a, d are also obtained by thermal water elimination of the carboxylic acids 4a, d, The red-coloured benzofuranols 8 react with acetic anhydride and benzoyl-chloride/pyridine, resp., to the weakly yellow esters 9.The structure of the products 8 and 9 is studied by UV-VIS derivative spectroscopy, by theoretical calculation of the dihedral angles and by H-1 and C-13 NMR spectroscopy. The H-1 and C-13 chemical shifts are completely assigned. The quinoxalines 8a-c and the quinoline 8d only exist in the hydroxy form.

  DOI：

  10.1002/prac.199733901130
• 作为产物：
  描述：

  2-(溴甲基)-3-甲基喹喔啉 、 水杨酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以50%的产率得到2-(3-Methyl-quinoxalin-2-ylmethoxy)-benzoic acid methyl ester
  参考文献：
  名称：

  Quinoxalines. IX. Reaction of 2-(Halogenomethyl)-quinoxalines and -quinoline with hydroxybenzoic acids and their esters

  摘要：

  In the presence of a base the title compounds react to products with ether structure (4,6), or with ester structure (3), or to structure 5 containing both functionalities in dependence on the mole ratio of the starting substances, on reaction conditions and on the substituent patterns in the hydroxybenzoic acid component.Under the influence of alkali hydroxide the m- and p-substituted compounds (6e-g) are saponified to the alkali salts of the carboxylic acid (4b,c). The o-substituted compounds (6a-d), however, are cyclized to the benzo[b]furanylquinoxalines (8). 8a, d are also obtained by thermal water elimination of the carboxylic acids 4a, d, The red-coloured benzofuranols 8 react with acetic anhydride and benzoyl-chloride/pyridine, resp., to the weakly yellow esters 9.The structure of the products 8 and 9 is studied by UV-VIS derivative spectroscopy, by theoretical calculation of the dihedral angles and by H-1 and C-13 NMR spectroscopy. The H-1 and C-13 chemical shifts are completely assigned. The quinoxalines 8a-c and the quinoline 8d only exist in the hydroxy form.

  DOI：

  10.1002/prac.199733901130

文献信息

• SARODNICK, GERHARD;KEMPTER, GERHARD;KUHNE, SABINE;VOGT, KARLA
  作者：SARODNICK, GERHARD、KEMPTER, GERHARD、KUHNE, SABINE、VOGT, KARLA

  DOI：——

  日期：——
• Quinoxalines. IX. Reaction of 2-(Halogenomethyl)-quinoxalines and -quinoline with hydroxybenzoic acids and their esters
  作者：G. Sarodnick、L. Hilfert、G. Kempter、E. Kleinpeter

  DOI：10.1002/prac.199733901130

  日期：——

  In the presence of a base the title compounds react to products with ether structure (4,6), or with ester structure (3), or to structure 5 containing both functionalities in dependence on the mole ratio of the starting substances, on reaction conditions and on the substituent patterns in the hydroxybenzoic acid component.Under the influence of alkali hydroxide the m- and p-substituted compounds (6e-g) are saponified to the alkali salts of the carboxylic acid (4b,c). The o-substituted compounds (6a-d), however, are cyclized to the benzo[b]furanylquinoxalines (8). 8a, d are also obtained by thermal water elimination of the carboxylic acids 4a, d, The red-coloured benzofuranols 8 react with acetic anhydride and benzoyl-chloride/pyridine, resp., to the weakly yellow esters 9.The structure of the products 8 and 9 is studied by UV-VIS derivative spectroscopy, by theoretical calculation of the dihedral angles and by H-1 and C-13 NMR spectroscopy. The H-1 and C-13 chemical shifts are completely assigned. The quinoxalines 8a-c and the quinoline 8d only exist in the hydroxy form.