3-benzyl-1-methyl-2-oxo-5-(4-trifluoromethylphenyl)-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-benzyl-1-methyl-2-oxo-5-(4-trifluoromethylphenyl)-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester
• 英文别名: Methyl 3-benzyl-1-methyl-2-oxo-5-[4-(trifluoromethyl)phenyl]imidazole-4-carboxylate
• 化学式: C₂₀H₁₇F₃N₂O₃
• 分子量: 390.362
• InChiKey: KDKVBVKBVXVCLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 苄基碘 、 alkaline earth salt of/the/ methylsulfuric acid 在 lithium tert-butoxide 、 sodium methylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-benzyl-1-methyl-2-oxo-5-(4-trifluoromethylphenyl)-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  N−H Insertion Reactions of Primary Ureas:  The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls

  摘要：

  Primary ureas have been used as substrates in rhodium-catalyzed N-H insertion reactions with an array of diazocarbonyls. The insertion reaction is efficient and gives excellent selectivity and yields. The products from the insertion reaction with diazoketones cyclize readily in the presence of acid to yield the corresponding imidazolones that can be further derivatized by N-alkylation with alkyl, allyl, and benzyl halides. Alternatively, the imidazolones were treated with phosphorus oxybromide to form the corresponding 2-bromoimidazoles that were further functionalized using a Suzuki coupling reaction.

  DOI：

  10.1021/jo048353u