5-fluoro-2-methylthio-3-methylpyrimidin-4-one | 72975-37-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-fluoro-2-methylthio-3-methylpyrimidin-4-one
• 英文别名: 5-fluoro-3-methyl-2-methysulfanylpyrimidin-4(3H)-one；5-fluoro-3-methyl-2-methylsulfanylpyrimidin-4(3H)-one；5-fluoro-3-methyl-2-methylsulfanyl-3H-pyrimidin-4-one；5-Fluoro-3-methyl-2-methylsulfanylpyrimidin-4-one
• CAS: 72975-37-2
• 化学式: C₆H₇FN₂OS
• 分子量: 174.199
• InChiKey: SQGWOOFOVQFVPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-methylthio-3-methylpyrimidin-4-one 以87%的产率得到
  参考文献：
  名称：

  GACEK M.; UNDHEIM K., ACTA CHEM. SCAND., 1979, B 33, NO 7, 515-518

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氟-2-(甲基硫代)-4(3H)-嘧啶酮 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-fluoro-2-methylthio-3-methylpyrimidin-4-one
  参考文献：
  名称：

  Kheifets; Kol'tsov; Khachaturov, Russian Journal of Organic Chemistry, 2000, vol. 36, # 9, p. 1373 - 1387

  摘要：

  DOI：

文献信息

• Effect of the Structure of 1- and 3-Methylpyrimidin-4-ones on the Rate of Nucleophilic Substitution of the 2-Methylsylfanyl Group
  作者：G. M. Kheifets、V. A. Gindin、T. A. Nikolova

  DOI：10.1023/b:rujo.0000034918.26019.44

  日期：2004.1

  Rate constants for substitution of the 2-methylsulfanyl group in 1- and 3-methyl-2-methylsulfanylpyrimidin-4-ones and their 5-fluoro analogs were measured in the reaction with butylamine, alkaline hydrolysis, and methanolysis. The rate of substitution in 1-methyl isomers having a zwitterionic structure is greater by a factor of similar to2 than the rate of substitution in 3-methyl isomers with conjugated double bonds in the ring. The presence of a fluorine atom in position 5 accelerates nucleophilic substitution in 1-methyl isomers, while 5-fluoro-3-methyl-2-methylsulfanylpyrimidin-4-ones react at a lower rate than their 5-unsubstituted analogs. According to the NMR data, the reactions involve formation of a tetrahedral intermediate. Anchimeric effect of the methyl group on N-1 hampers attack by basic reagent on the C-6 atom.
• Kheifets; Kol'tsov; Khachaturov, Russian Journal of Organic Chemistry, 2000, vol. 36, # 9, p. 1373 - 1387
  作者：Kheifets、Kol'tsov、Khachaturov、Gindin

  DOI：——

  日期：——
• GACEK M.; UNDHEIM K., ACTA CHEM. SCAND., 1979, B 33, NO 7, 515-518
  作者：GACEK M.、 UNDHEIM K.

  DOI：——

  日期：——