ethyl 3-methyl-2-oxo-4-phenyl-1H-imidazole-5-carboxylate | 501691-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-methyl-2-oxo-4-phenyl-1H-imidazole-5-carboxylate
• CAS: 501691-19-6
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: ULMSAYJHCILMAE-UHFFFAOYSA-N

物化性质

• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-methyl-2-oxo-4-phenyl-1H-imidazole-5-carboxylate 在 三溴氧磷 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以87%的产率得到2-bromo-1-methyl-5-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：

  (1Z)-2-偶氮基-1-乙氧基-3-氧代-3-苯基-1-丙烯-1-醇 在 辛酸铑 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 1.0h， 生成 ethyl 3-methyl-2-oxo-4-phenyl-1H-imidazole-5-carboxylate
  参考文献：
  名称：

  伯脲类化合物的铑类​​胡萝卜素NH插入反应：咪唑酮的溶液和固相合成。

  摘要：

  [反应：见正文]报道了咪唑酮的溶液和固相合成。制备这些化合物的关键步骤是伯尿素向高反应性铑类胡萝卜素中间体的NH插入反应。通常，在伯尿素的存在下用羧酸铑催化剂处理可溶的或与载体结合的α-重氮-β-酮酸酯，得到相应的NH插入产物。这些插入产物的随后的酸催化的环脱水作用提供了所需的咪唑酮产物。

  DOI：

  10.1021/ol020244j

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.
• Rhodium Carbenoid N−H Insertion Reactions of Primary Ureas:  Solution and Solid-Phase Synthesis of Imidazolones
  作者：Sang-Hyeup Lee、Bruce Clapham、Guido Koch、Jürg Zimmermann、Kim D. Janda

  DOI：10.1021/ol020244j

  日期：2003.2.1

  [reaction: see text] The solution and solid-phase synthesis of imidazolones is reported. The key step for the preparation of these compounds is the N-H insertion reaction of primary ureas into highly reactive rhodium carbenoid intermediates. Typically, a soluble or support-bound alpha-diazo-beta-ketoester is treated with a rhodium carboxylate catalyst in the presence of a primary urea to give the corresponding

  [反应：见正文]报道了咪唑酮的溶液和固相合成。制备这些化合物的关键步骤是伯尿素向高反应性铑类胡萝卜素中间体的NH插入反应。通常，在伯尿素的存在下用羧酸铑催化剂处理可溶的或与载体结合的α-重氮-β-酮酸酯，得到相应的NH插入产物。这些插入产物的随后的酸催化的环脱水作用提供了所需的咪唑酮产物。