5-methyl-2-oxo-1-phenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester | 14058-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-2-oxo-1-phenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-methyl-2-oxo-1-phenyl-2,3-dihydro-1H-imidazole-4-carboxylate；5-methyl-2-oxo-1-phenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester；ethyl 4-methyl-2-oxo-3-phenyl-1H-imidazole-5-carboxylate
• CAS: 14058-84-5
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: OMIJTOUKIUTYFL-UHFFFAOYSA-N

物化性质

• 熔点：
  188-189 °C
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：

  5-methyl-2-oxo-1-phenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester 在 三溴氧磷 作用下， 以 苯 为溶剂， 反应 6.0h， 以76%的产率得到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
• 作为产物：
  描述：

  苯基脲 在 rhodium(II) octanoate 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 3.5h， 生成 5-methyl-2-oxo-1-phenyl-2,3-dihydro-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

• Design and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives bearing an imidazolone moiety as c-Met kinase inhibitors
  作者：Weike Liao、Gang Hu、Zhuang Guo、Deyu Sun、Lixia Zhang、Yanxin Bu、Yingxiu Li、Yajing Liu、Ping Gong

  DOI：10.1016/j.bmc.2015.06.026

  日期：2015.8

  A series of 4-(2-fluorophenoxy)quinoline derivatives containing an imidazolone moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, H460, HT-29 and MKN-45). Most compounds showed moderate to excellent activities in enzyme and cellular assays. The most promising analog, 58 (c-Met IC50 = 1.42 nM), displayed 2.1-

  设计，合成并评估了一系列含咪唑酮部分的4-（2-氟苯氧基）喹啉衍生物对c-Met激酶和四种癌细胞系（A549，H460，HT-29和MKN-45）的体外生物学活性）。大多数化合物在酶和细胞分析中均显示中等至出色的活性。 与福瑞替尼相比，最有前途的类似物58（c-Met IC 50 = 1.42 nM）对H460和MKN-45细胞株分别显示出2.1倍，8.6倍的增长。对结构-活性关系的分析表明，邻位取代的苯环以及N-未取代的咪唑啉酮连接基有利于抗肿瘤活性。
• Phenylethynyl and styryl derivatives of imidazole and fused ring heterocycles
  申请人：——

  公开号：US20020128263A1

  公开（公告）日：2002-09-12

  This invention relates to a compound and the use of the compound of the formula 1 wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the description, A signifies —CH═CH— or —C≡C—; and B signifies 2 wherein R 6 to R 26 , X and Y are as defined in the specification or a pharmaceutically acceptable salt thereof, for use in pharmaceutical compositions for the treatment or prevention of mGluR5 receptor mediated disorders.

  本发明涉及一种化合物及该化合物的使用，其化学式为1，其中R1、R2、R3、R4和R5如描述中所定义，A表示—CH═CH—或—C≡C—；B表示2，其中R6到R26、X和Y如规范中所定义或其药用可接受的盐，用于制备用于治疗或预防mGluR5受体介导的疾病的制药组合物。
• 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。
• PHENYLETHENYL OR PHENYLETHINYL DERIVATIVES AS GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1349839A1

  公开（公告）日：2003-10-08
• US6706707B2
  申请人：——

  公开号：US6706707B2

  公开（公告）日：2004-03-16