6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline | 263715-88-4

• 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: 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline
• 英文别名: Methyl 3-methyl-2-(2-phenylethynyl)quinoxaline-6-carboxylate
• CAS: 263715-88-4
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: IUSWKMXDWKJPGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以49%的产率得到(E)-6-methoxycarbonyl-3-methyl-2-styrylquinoxaline
  参考文献：
  名称：

  Synthesis of Quinoxaline Derivatives Bearing the Styryl and Phenylethynyl Groups and Application to a Fluorescence Derivatization Reagent

  摘要：

  The cross-coupling of 2-chloro-6-methoxycarbonyl-3-methylquinoxaline (2) and 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one (7) with phenylacetylene in the presence of Pd(PPh3)(4) gave 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline (3) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)phenylethynylquinoxalin-2(1H)-one (9), respectively. Compounds (3 and 9) were further converted into the corresponding olefinic compounds, 6-methoxycarbonyl-3-methyl-2-styrylquinoxaline (4) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)styrylquinoxalin-2(1H)-one (10), by partial hydrogenation on palladium catalysts such as Lindlar catalyst and Pd/BaSO4-quinoline, but the conformation of the resulting olefins was unexpectedly E-form. These quinoxaline derivatives showed fluorescent emission bands at a range from 398 to 467 nm in MeCN when the excitation wavelength of 353-405 nm was applied. Further, 3-(4-chlorocarbonyl)phenylethynyl-7-methoxy-1-methylquinoxalin-2(1H)-one (12) was demonstrated to be applicable to a fluorescence derivatization reagent for amines.

  DOI：

  10.3987/com-99-s61
• 作为产物：
  描述：

  6-methoxycarbonyl-3-methylquinoxaline-2(1H)-one 在 四(三苯基膦)钯 、 potassium acetate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline
  参考文献：
  名称：

  Synthesis of Quinoxaline Derivatives Bearing the Styryl and Phenylethynyl Groups and Application to a Fluorescence Derivatization Reagent

  摘要：

  The cross-coupling of 2-chloro-6-methoxycarbonyl-3-methylquinoxaline (2) and 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one (7) with phenylacetylene in the presence of Pd(PPh3)(4) gave 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline (3) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)phenylethynylquinoxalin-2(1H)-one (9), respectively. Compounds (3 and 9) were further converted into the corresponding olefinic compounds, 6-methoxycarbonyl-3-methyl-2-styrylquinoxaline (4) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)styrylquinoxalin-2(1H)-one (10), by partial hydrogenation on palladium catalysts such as Lindlar catalyst and Pd/BaSO4-quinoline, but the conformation of the resulting olefins was unexpectedly E-form. These quinoxaline derivatives showed fluorescent emission bands at a range from 398 to 467 nm in MeCN when the excitation wavelength of 353-405 nm was applied. Further, 3-(4-chlorocarbonyl)phenylethynyl-7-methoxy-1-methylquinoxalin-2(1H)-one (12) was demonstrated to be applicable to a fluorescence derivatization reagent for amines.

  DOI：

  10.3987/com-99-s61