2-[(4-methylene-5-oxo-2-phenyltetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione | 1259224-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-[(4-methylene-5-oxo-2-phenyltetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione
• 英文别名: 2-[(4-Methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2h,4h)-dione；2-[(4-methylidene-5-oxo-2-phenyloxolan-2-yl)methyl]-1,2,4-triazine-3,5-dione
• CAS: 1259224-37-7
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: MUSXFHAISQTFPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴苯乙酮 在 对苯二酚 、 锌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 生成 2-[(4-methylene-5-oxo-2-phenyltetrahydrofuran-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

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.