2-bromo-5-methyl-1-phenyl-1H-imidazole-4-carboxylic acid ethyl ester | 819047-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-bromo-5-methyl-1-phenyl-1H-imidazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-bromo-5-methyl-1-phenylimidazole-4-carboxylate
• CAS: 819047-37-5
• 化学式: C₁₃H₁₃BrN₂O₂
• 分子量: 309.162
• InChiKey: TWGCMTFEKRHLNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-5-methyl-1-phenyl-1H-imidazole-4-carboxylic acid ethyl ester 、 4-(叔丁基二甲基硅氧基)苯基硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以93%的产率得到2-(4-(tert-butyldimethylsilanyloxy)phenyl)-5-methyl-1-phenyl-1H-imidazole-4-carboxylic acid ethyl 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
• 作为产物：
  描述：

  苯基脲 在 rhodium(II) octanoate 、 三氟乙酸 、 三溴氧磷 作用下， 以 1,2-二氯乙烷 、 甲苯 、 苯 为溶剂， 反应 9.5h， 生成 2-bromo-5-methyl-1-phenyl-1H-imidazole-4-carboxylic acid ethyl 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

文献信息

• N−H Insertion Reactions of Primary Ureas:  The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls
  作者：Sang-Hyeup Lee、Kazuhiro Yoshida、Hana Matsushita、Bruce Clapham、Guido Koch、Jürg Zimmermann、Kim D. Janda

  DOI：10.1021/jo048353u

  日期：2004.12.1

  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.