5-thioxo-[1,2,4]oxadiazinan-3-one | 59696-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: 5-thioxo-[1,2,4]oxadiazinan-3-one
• 英文别名: 6H-1,2,4-oxadiazin-3-one-5-thione；6H-1,2,4-oxadiazin-3(2H)-one-5(4H)-thione；6H-1,2,4-Oxadiazin-3(2H)-on-5(4H)-thion；2H-1,2,4-Oxadiazin-3(4H)-one, dihydro-5-thioxo-；5-sulfanylidene-1,2,4-oxadiazinan-3-one
• CAS: 59696-55-8
• 化学式: C₃H₄N₂O₂S
• 分子量: 132.143
• InChiKey: IOZJTSMYDXDENP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  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-6H-[1,2,4]oxadiazin-3-one
  参考文献：
  名称：

  嘧啶和嘧啶核苷的6-Oxa类似物。5-氨基-6H-1,2,4-恶二嗪-3（2H）-1,2-β-D-呋喃呋喃糖基-6H-1,2,4-恶二嗪-3,5（2H，4H）-的合成二酮及相关衍生物。

  摘要：

  DOI：

  10.1021/jo00881a013
• 作为产物：
  描述：

  [1,2,4]oxadiazinane-3,5-dione 在 tetraphosphorus decasulfide 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-thioxo-[1,2,4]oxadiazinan-3-one
  参考文献：
  名称：

  嘧啶和嘧啶核苷的6-Oxa类似物。5-氨基-6H-1,2,4-恶二嗪-3（2H）-1,2-β-D-呋喃呋喃糖基-6H-1,2,4-恶二嗪-3,5（2H，4H）-的合成二酮及相关衍生物。

  摘要：

  DOI：

  10.1021/jo00881a013

文献信息

• 5-Substituted amino-6H-1,2,4-oxadiazin-3-(2H)-ones
  申请人：The Dow Chemical Company

  公开号：US04459403A1

  公开（公告）日：1984-07-10

  This invention relates to novel 5-substituted amino-6H-1,2,4-oxadiazin-3(2H)-ones wherein the 5-amino group is N-substituted with a C.sub.4-20 alkyl or alkenyl group, a phenyl group with an amide, alkoxy or alkyl ester in the meta or para position, a pyridinyl group substituted with one or two alkyl groups, a 3,4,5-trialkoxyphenylmethylene group, or the nitrogen attached to the 5 carbon is part of a heterocyclic ring wherein the heterocyclic ring is imidazole, imidazolidinedione, imidazolidinyl, morpholinyl, piperazinyl or pyrrolidinyl.

  该发明涉及新型的5-取代氨基-6H-1,2,4-噁二嗪-3(2H)-酮，其中5-氨基基团被N-取代为C.sub.4-20烷基或烯基基团，带有酰胺、烷氧基或烷基酯的苯基在间位或对位，带有一或两个烷基基团的吡啶基团，3,4,5-三烷氧基苯甲基基团，或者与5碳相连的氮原子是异环戒的一部分，其中异环戒是咪唑、咪唑二酮、咪唑啉、吗啉、哌嗪或吡咯啉。
• 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.
• PAUL, A. M.
  作者：PAUL, A. M.

  DOI：——

  日期：——
• 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：——
• 6-Oxa analogs of pyrimidines and pyrimidine nucleosides. Synthesis of 5-amino-6H-1,2,4-oxadiazin-3(2H)-one, 2-.beta.-D-ribofuranosyl-6H-1,2,4-oxadiazine-3,5(2H,4H)-dione, and related derivatives
  作者：Phillip T. Berkowitz、Roland K. Robins、Phoebe Dea、Robert A. Long

  DOI：10.1021/jo00881a013

  日期：1976.9