6-methyl-4-oxo-2-thio-2,3-dihydro-4H-1,3-oxazine | 2911-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 6-methyl-4-oxo-2-thio-2,3-dihydro-4H-1,3-oxazine
• 英文别名: 6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine；6-Methyl-4-oxo-2-thio-2,3-dihydro-4H-1,3-oxazin；6-Methyl-2-thioxo-1,3-oxazin-4(3H)-on；6-Methyl-2-thioxo-2,3-dihydro-<1,3>oxazin-4-on；2H-3,4-dihydro-6-methyl-2-thioxo-1,3-oxazin-4-one；6-methyl-2-thioxo-2,3-dihydro-[1,3]oxazin-4-one；4H-1,3-Oxazin-4-one, 2,3-dihydro-6-methyl-2-thioxo-；6-methyl-2-sulfanylidene-1,3-oxazin-4-one
• CAS: 2911-22-0
• 化学式: C₅H₅NO₂S
• 分子量: 143.166
• InChiKey: RDSLKLDUGTWBPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-4-oxo-2-thio-2,3-dihydro-4H-1,3-oxazine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以57%的产率得到乙酰乙酸甲酯
  参考文献：
  名称：

  Sasaki, Tadashi; Ito, Eikoh; Asai, Koji, Heterocycles, 1983, vol. 20, # 6, p. 1089 - 1097

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氧丁酸 、 lead(II) thiocyanate 在 二溴三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到6-methyl-4-oxo-2-thio-2,3-dihydro-4H-1,3-oxazine
  参考文献：
  名称：

  Reaction of Ph₃P(SCN)₂with Further Orthohydroxy Carboxylic Acid Systems, Including Substituted β-Keto Acids: Synthesis of Novel 2-Thio-1,3-oxazines and Their Subsequent Transformation with Amines

  摘要：

  We now report the first reaction of Ph3P(SCN)2 with 4,6-dihydroxy-5-methylisophthalic acid to give 10-methyl-2,8-dithio-1,3-oxazino-1,3-benzoxazine-4,6-dione. Also, the enol tautomer has been utilized in the reaction of -keto acids with Ph3P(SCN)2 to give novel 2-thio-1,3-oxazines. Subsequent reaction of the 2-thio-1,3-oxazines with benzylamine resulted in opening of the oxazine ring and gave novel dibenzylamino-enamides, which could be cyclized to thiouracils. The reaction of 2-thio-1,3-oxazines with morpholine at low temperature led to the production of unstable 2-Mercapto-2-morpholino-1,3-oxazines. 2-Mercapto-2-morpholin-4-yl-2,3,5,6,7,8-hexahydro-4H-1,3-benzoxazin-4-one was observed to lose H2S at room temperature to give 2-morpholin-4-yl-5,6,7,8-tetrahydro-4H-1,3-benzoxazin-4-one, which was subsequently tested and found to exhibit some antiplatelet activity.

  DOI：

  10.1080/00397910802267204

文献信息

• Pyrimidine derivatives
  申请人：Imperial Chemical Industries Plc

  公开号：US05223505A1

  公开（公告）日：1993-06-29

  This invention concerns novel aminopyrimidinium salts of the formula I: ##STR1## in which R.sup.1 is alkyl, alkenyl, cycloalkyl, phenyl, phenylalkyl or cycloalkyl-alkyl; one of R.sup.2 and R.sup.6 is a basic group selected from amino, alkylamino, dialkylamino of up to eight carbon atoms, pyrrolidino, piperidino and morpholino; and the other of R.sup.2 and R.sup.6 is hydrogen, alkyl, alkenyl, alkoxyalkyl, phenyl, phenylalkyl, cycloalkyl or cycloalkyl-alkyl; or both of R.sup.2 and R.sup.6 are basic groups as mentioned above; and R.sup.5 is hydrogen, (1-4C)alkyl or (3-6C)alkenyl; or R.sup.2 is a basic group as mentioned above, and R.sup.5 and R.sup.6 together form alkylene or, together with the appendant carbon atoms of the pyrimidine ring, complete a benzene ring; R.sup.4 is hydrogen, alkyl, cycloalkyl-alkyl, alkenyl, alkynyl or phenylalkyl; or R.sup.4 is an optionally substitutued alkylene or alkenylene linked to the nitrogen atom of the group Q.A.N--, either of which linking groups may thereby completing a ring including two adjacent carbon atoms of Q, the carbon atoms of A and the adjacent nitrogen atom of the group --A.N--; A is a direct bond to the the group --N(R.sup.4)-- or is alkylene or oxyalkylene; Q is a pyridyl, furyl, thienyl or phenyl moiety; and Y is a physiologically acceptable anion; but excluding a number of compounds specified hereinafter. The invention also includes certain closely related anhydro-base derivatives which, like the formula I compounds, possess beneficial effects on the cardiovascular system (and in particular beneficial effects modulated via the sino-atrial node). Also included are pharmaceutical compositions containing the formula I compound (or a related anhydro-base) as active ingredient, and processes for the manufacture of the various novel compounds.

  这项发明涉及式I的新型氨基嘧啶盐：其中R.sup.1是烷基，烯烃基，环烷基，苯基，苯基烷基或环烷基-烷基；R.sup.2和R.sup.6中的一个是从氨基，烷基氨基，最多含有八个碳原子的二烷基氨基，吡咯啉基，哌啶基和吗啉基中选择的一种碱性基团；而另一个是氢，烷基，烯烃基，烷氧基烷基，苯基，苯基烷基，环烷基或环烷基-烷基；或者R.sup.2和R.sup.6都是上述提到的碱性基团；R.sup.5是氢，（1-4C）烷基或（3-6C）烯烃基；或者R.sup.2是上述提到的碱性基团，而R.sup.5和R.sup.6一起形成亚烷基或者与嘧啶环的附加碳原子一起形成苯环；R.sup.4是氢，烷基，环烷基-烷基，烯烃基，炔烃基或苯基烷基；或者R.sup.4是可选取代的烷基或烯基与Q.A.N--基团的氮原子相连，这些连接基团可能形成包括Q的两个相邻碳原子，A的碳原子和--A.N--基团的相邻氮原子的环；A是直接连接到--N(R.sup.4)--基团的键或者是烷基或氧基烷基；Q是吡啶基，呋喃基，噻吩基或苯基基团；Y是生理上可接受的阴离子；但不包括下文中指定的一些化合物。该发明还包括某些紧密相关的无水碱衍生物，类似于式I化合物，对心血管系统具有有益效果（尤其是通过窦房结调节的有益效果）。还包括含有式I化合物（或相关的无水碱）作为活性成分的药物组合物，以及用于制造各种新型化合物的方法。
• Ahmed,S. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1969 - 1975
  作者：Ahmed,S. et al.

  DOI：——

  日期：——
• The synthesis and rearrangement of 1,3-oxazines
  作者：R.N. Warrener、E.N. Cain

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• Yamamoto, Yutaka; Morita, Yasuo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 8, p. 2957 - 2962
  作者：Yamamoto, Yutaka、Morita, Yasuo

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• SASAKI, TADASHI;ITO, EIKOH;ASAI, KOJI, HETEROCYCLES, 1983, 20, N 6, 1089-1097
  作者：SASAKI, TADASHI、ITO, EIKOH、ASAI, KOJI

  DOI：——

  日期：——