4-fluoro-6-(3-nitrophenyl)-2-methylpyrimidine 1-oxide | 1404219-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-fluoro-6-(3-nitrophenyl)-2-methylpyrimidine 1-oxide
• 英文别名: 4-Fluoro-2-methyl-6-(3-nitrophenyl)-1-oxidopyrimidin-1-ium；4-fluoro-2-methyl-6-(3-nitrophenyl)-1-oxidopyrimidin-1-ium
• CAS: 1404219-97-1
• 化学式: C₁₁H₈FN₃O₃
• 分子量: 249.201
• InChiKey: YRSKDZRITCATAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-硝基苯乙烯 在 苄基三乙基氯化铵 、 nitrosonium tetrafluoroborate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 4-fluoro-6-(3-nitrophenyl)-2-methylpyrimidine 1-oxide
  参考文献：
  名称：

  Three-Component Heterocyclization of gem-Bromofluorocyclopropanes with NOBF₄: Access to 4-Fluoropyrimidine N-Oxides

  摘要：

  Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.

  DOI：

  10.1021/jo301880m

文献信息

• Three-Component Heterocyclization of <i>gem</i>-Bromofluorocyclopropanes with NOBF₄: Access to 4-Fluoropyrimidine <i>N</i>-Oxides
  作者：Kseniya N. Sedenkova、Elena B. Averina、Yuri K. Grishin、Andrei G. Kutateladze、Victor B. Rybakov、Tamara S. Kuznetsova、Nikolay S. Zefirov

  DOI：10.1021/jo301880m

  日期：2012.11.2

  Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.