2-Methyl-1,2,4-oxadiazin-3,5-dion | 5767-08-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 2-Methyl-1,2,4-oxadiazin-3,5-dion
• 英文别名: 2-methyl-[1,2,4]oxadiazinane-3,5-dione；2-methyl-6H-1,2,4-oxadiazine-3,5-dione；2-Methyl-1,2,4-oxadiazinane-3,5-dione
• CAS: 5767-08-8
• 化学式: C₄H₆N₂O₃
• 分子量: 130.103
• InChiKey: ALVJZNWTHGTTPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 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：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methyl-1,2,4-oxadiazin-3,5-dion 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-methyl-5-thioxo-[1,2,4]oxadiazinan-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
• 作为产物：
  描述：

  (1-methyl-ureidooxy)-acetic acid ethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 2-Methyl-1,2,4-oxadiazin-3,5-dion
  参考文献：
  名称：

  Kornowski,H. et al., Bulletin de la Societe Chimique de France, 1966, p. 683 - 686

  摘要：

  DOI：

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：——
• Kornowski,H. et al., Bulletin de la Societe Chimique de France, 1966, p. 683 - 686
  作者：Kornowski,H. et al.

  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.