1-methyl-2,5-diphenyl-1H-imidazole-4-carboxylic acid ethyl ester | 15994-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-2,5-diphenyl-1H-imidazole-4-carboxylic acid ethyl ester
• 英文别名: 1-Methyl-2,5-diphenyl-imidazol-carbonsaeure-(4)-aethylester；1-Methyl-2,5-diphenyl-imidazol-carbonsaeure-(4)-ethylester；Ethyl 1-methyl-2,5-diphenylimidazole-4-carboxylate
• CAS: 15994-88-4
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: MKFSKERAWYMEQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 3-methyl-2-oxo-4-phenyl-1H-imidazole-5-carboxylate 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 、 三溴氧磷 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 1-methyl-2,5-diphenyl-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

• Neurokinin-3 receptor modulators: diaryl imidazole derivatives
  申请人：Maynard D. George

  公开号：US20050148601A1

  公开（公告）日：2005-07-07

  The invention relates to compounds of general Formula I: wherein the variables are as defined herein. Also provided are pharmaceutical compositions comprising such compounds, and methods for treating patients suffering from a disorder responsive to neurokinin-3 receptor modulation. NK-3 receptor modulators provided herein are also useful as probes for the localization of NK-3 receptors.

  该发明涉及一般式I的化合物： 其中变量如本文所定义。还提供包含这种化合物的药物组合物，以及治疗对神经激肽-3受体调节敏感的患者的方法。本文提供的NK-3受体调节剂也可用作定位NK-3受体的探针。
• [EN] 2,5-DIARYL-1H-IMIDAZOLE-4-CARBOXAMIDES AS NEUROKININ-3 RECEPTOR MODULATORS FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM AND PERIPHERAL DISEASES<br/>[FR] 2,5-DIARYL-1H-IMIDAZOLE-4-CARBOXAMIDES UTILISES EN TANT QUE MODULATEURS DES RECEPTEURS DE LA NEUROKININE-3 POUR LE TRAITEMENT DE MALADIES DU SYSTEME NERVEUX CENTRAL ET PERIPHERIQUE
  申请人：NEUROGEN CORP

  公开号：WO2005066137A1

  公开（公告）日：2005-07-21

  The invention relates to compounds of general Formula I: wherein the variables are as defined herein. Also provided are pharmaceutical compositions comprising such compounds, and methods for treating patients suffering from a disorder responsive to neurokinin-3 receptor modulation. NK-3 receptor modulators provided herein are also useful as probes for the localization of NK-3 receptors.
• 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.