1,3-dimethyl-6-(p-tolyl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)dione | 1632165-11-7

• 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: 1,3-dimethyl-6-(p-tolyl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)dione
• 英文别名: 1,3-Dimethyl-6-(4-methylphenyl)-5-(trifluoromethyl)pyrimidine-2,4-dione；1,3-dimethyl-6-(4-methylphenyl)-5-(trifluoromethyl)pyrimidine-2,4-dione
• CAS: 1632165-11-7
• 化学式: C₁₄H₁₃F₃N₂O₂
• 分子量: 298.265
• InChiKey: WCLMKFXWPINLIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 在 potassium fluoride 、 copper(l) iodide 、 1,10-菲罗啉 、 copper diacetate 、 palladium diacetate 、 cesium fluoride 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1,3-dimethyl-6-(p-tolyl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)dione
  参考文献：
  名称：

  C-H Trifluoromethylations of 1,3-Dimethyluracil and Reactivity of the Products in C-H Arylations

  摘要：

  Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5-(trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave the desired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.

  DOI：

  10.3987/com-14-12958

文献信息

• C-H Trifluoromethylations of 1,3-Dimethyluracil and Reactivity of the Products in C-H Arylations
  作者：Michal Hocek、Miroslava Ćerňová、Radek Pohl、Blanka Klepetářová

  DOI：10.3987/com-14-12958

  日期：——

  Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5-(trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave the desired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.