5-amino-2-methyl-6H-[1,2,4]oxadiazin-3-one | 60904-06-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-amino-2-methyl-6H-[1,2,4]oxadiazin-3-one
• 英文别名: 5-Amino-2-methyl-2H-1,2,4-oxadiazin-3(6H)-one；5-imino-2-methyl-1,2,4-oxadiazinan-3-one
• CAS: 60904-06-5
• 化学式: C₄H₇N₃O₂
• mdl: MFCD19208621
• 分子量: 129.118
• InChiKey: YUJCNWFXYDBKTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-methyl-5-thioxo-[1,2,4]oxadiazinan-3-one 在 氨 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-amino-2-methyl-6H-[1,2,4]oxadiazin-3-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of certain 6H-1,2,4-oxadiazin-3(2H)-ones

  摘要：

  Treatment of 6H-1,2,4-oxadiazin-3(2H)-one-5(4H)-thione (2) with hydroxylamine, hydrazine, methylamine, or benzylamine afforded the corresponding N5-substituted 5-amino-6H-1,2,4-oxadiazin-3(2H)-ones 3c-f. Refluxing a dioxane solution of 6H-1,2,4-oxiazine-3,5(2H,4H)-dione (1) with benzylamine or aminodiphenylmethane and hexamethyldisilazane in the presence of ammonium sulfate gave 5-benzylamino-6H-1,2,4-oxadiazin-3(2H)-one (3f) and the corresponding 5-diphenylmethylamino derivative 3g. Reaction of 1 with methyl iodide, benzyl chloride, dihydropyran, dihydrofuran, or benzyloxycarbonyl chloride afforded the corresponding 2-substituted 6H-1,2,4-oxadiazine-3,5(2H,4H)-diones 6a-e. Reaction of 2-methyl-6H-1,2,4-oxadiazine-3,5(2H,4H)-dione (6a) or the corresponding 2-benzyl derivative 6b with phosphorus pentasulfide in dioxane gave 2-methyl-6H-1,2,4-oxadiazin-3(2H)-one-5(4H)-thione (8a) and the corresponding 2-benzyl derivative 8b, respectively. Reaction of 8a with ammonia in dioxane afforded 2-methyl-5-amino-6H-1,2,4-oxadiazin-3(2H)-one (9). The degree of in vitro activity and the presence of antibacterial activity in the urine of animals given 5-amino-6H-1,2,4-oxadiazin-3(2H)-one (3a) by oral route of administration prompted selection of this compound for further study.

  DOI：

  10.1021/jm00211a028

文献信息

• BERKOWITZ P. T.; LONG R. A.; DEA P.; ROBINS R. K.; MATTHEWS T. R., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 1, 134-138
  作者：BERKOWITZ P. T.、 LONG R. A.、 DEA P.、 ROBINS R. K.、 MATTHEWS T. R.

  DOI：——

  日期：——
• Synthesis and antimicrobial activity of certain 6H-1,2,4-oxadiazin-3(2H)-ones
  作者：Phillip T. Berkowitz、Robert A. Long、Phoebe Dea、Roland K. Robins、Thomas R. Matthews

  DOI：10.1021/jm00211a028

  日期：1977.1

  Treatment of 6H-1,2,4-oxadiazin-3(2H)-one-5(4H)-thione (2) with hydroxylamine, hydrazine, methylamine, or benzylamine afforded the corresponding N5-substituted 5-amino-6H-1,2,4-oxadiazin-3(2H)-ones 3c-f. Refluxing a dioxane solution of 6H-1,2,4-oxiazine-3,5(2H,4H)-dione (1) with benzylamine or aminodiphenylmethane and hexamethyldisilazane in the presence of ammonium sulfate gave 5-benzylamino-6H-1,2,4-oxadiazin-3(2H)-one (3f) and the corresponding 5-diphenylmethylamino derivative 3g. Reaction of 1 with methyl iodide, benzyl chloride, dihydropyran, dihydrofuran, or benzyloxycarbonyl chloride afforded the corresponding 2-substituted 6H-1,2,4-oxadiazine-3,5(2H,4H)-diones 6a-e. Reaction of 2-methyl-6H-1,2,4-oxadiazine-3,5(2H,4H)-dione (6a) or the corresponding 2-benzyl derivative 6b with phosphorus pentasulfide in dioxane gave 2-methyl-6H-1,2,4-oxadiazin-3(2H)-one-5(4H)-thione (8a) and the corresponding 2-benzyl derivative 8b, respectively. Reaction of 8a with ammonia in dioxane afforded 2-methyl-5-amino-6H-1,2,4-oxadiazin-3(2H)-one (9). The degree of in vitro activity and the presence of antibacterial activity in the urine of animals given 5-amino-6H-1,2,4-oxadiazin-3(2H)-one (3a) by oral route of administration prompted selection of this compound for further study.