5-氟-2-甲氧基-1-甲基-4(1H)-嘧啶酮 | 729593-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氟-2-甲氧基-1-甲基-4(1H)-嘧啶酮
• 英文名称: 5-fluoro-2-methoxy-1-methylpyrimidin-4(1H)-one
• 英文别名: 5-fluoro-2-methoxy-1-methylpyrimidin-4-one
• CAS: 729593-67-3
• 化学式: C₆H₇FN₂O₂
• 分子量: 158.132
• InChiKey: FLRRUJCGFDLWHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium methoxide-d3 、 5-氟-2-甲氧基-1-甲基-4(1H)-嘧啶酮 以 氘代二甲亚砜 为溶剂， 生成
  参考文献：
  名称：

  Effect of the Structure of 1- and 3-Methylpyrimidin-4-ones on the Rate of Nucleophilic Substitution of the 2-Methylsylfanyl Group

  摘要：

  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.

  DOI：

  10.1023/b:rujo.0000034918.26019.44
• 作为产物：
  描述：

  sodium methylate 、 5-fluoro-1-methyl-2-methylsulfanylpyrimidin-4(1H)-one 以 甲醇 为溶剂， 以71%的产率得到5-氟-2-甲氧基-1-甲基-4(1H)-嘧啶酮
  参考文献：
  名称：

  Effect of the Structure of 1- and 3-Methylpyrimidin-4-ones on the Rate of Nucleophilic Substitution of the 2-Methylsylfanyl Group

  摘要：

  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.

  DOI：

  10.1023/b:rujo.0000034918.26019.44