5,6-dimethyl-2-thioxo-2,3-dihydro-4H-1,3-oxazin-4-one | 1094484-85-1

• 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: 5,6-dimethyl-2-thioxo-2,3-dihydro-4H-1,3-oxazin-4-one
• 英文别名: 5,6-Dimethyl-2-sulfanylidene-1,3-oxazin-4-one
• CAS: 1094484-85-1
• 化学式: C₆H₇NO₂S
• 分子量: 157.193
• InChiKey: CGRFTGKWESSFMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 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：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dimethyl-2-thioxo-2,3-dihydro-4H-1,3-oxazin-4-one 、 苄胺 以 二氯甲烷 为溶剂， 以69%的产率得到(2Z)-3-benzylamino-N-[(benzylamino)carbonothioyl]-2-methylbut-2-enamide
  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
• 作为产物：
  描述：

  2-甲基乙酰乙酸 、 lead(II) thiocyanate 在 二溴三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到5,6-dimethyl-2-thioxo-2,3-dihydro-4H-1,3-oxazin-4-one
  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

• 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
  作者：Kaylene M. Pritchard、Jasim Al-Rawi

  DOI：10.1080/00397910802267204

  日期：2008.11.3

  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.