2-(2-oxo-2-(4-fluorophenyl)ethyl)-1,2,4-triazine-3,5(2H,4H)-dione | 61959-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-oxo-2-(4-fluorophenyl)ethyl)-1,2,4-triazine-3,5(2H,4H)-dione
• 英文别名: 2-[2-(4-fluoro-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazine-3,5-dione；2-[2-(4-Fluorophenyl)-2-oxoethyl]-1,2,4-triazine-3,5(2H,4H)-dione；2-[2-(4-fluorophenyl)-2-oxoethyl]-1,2,4-triazine-3,5-dione
• CAS: 61959-08-8
• 化学式: C₁₁H₈FN₃O₃
• 分子量: 249.201
• InChiKey: GKQKPZYWNYIISA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-2-(4-fluorophenyl)ethyl)-1,2,4-triazine-3,5(2H,4H)-dione 、 2-溴甲基丙烯酸乙酯 在 对苯二酚 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以79.3%的产率得到2-[(4-methylene-5-oxo-2-(4-fluorophenyl)tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of 6-azapyrimidines with α-methylene-γ-(4-substituted phenyl)-γ-butyrolactone pharmacophores

  摘要：

  A series of 6-substituted 2-[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris.

  DOI：

  10.1007/s00044-010-9438-7
• 作为产物：
  描述：

  3,5-二[(三甲基硅)氧]基-1,2,4-三嗪 、 2-溴-4'-氟苯乙酮 以 乙腈 为溶剂， 生成 2-(2-oxo-2-(4-fluorophenyl)ethyl)-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of 6-azapyrimidines with α-methylene-γ-(4-substituted phenyl)-γ-butyrolactone pharmacophores

  摘要：

  A series of 6-substituted 2-[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris.

  DOI：

  10.1007/s00044-010-9438-7

文献信息

• Synthesis and antibacterial evaluation of 6-azapyrimidines with α-methylene-γ-(4-substituted phenyl)-γ-butyrolactone pharmacophores
  作者：Po-Jui Huang、Kuan-Han Lee

  DOI：10.1007/s00044-010-9438-7

  日期：2011.9

  A series of 6-substituted 2-[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris.