2-oxo-1,5-diphenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester | 501691-18-5

• 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-oxo-1,5-diphenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2-oxo-1,5-diphenyl-2,3-dihydro-1H-imidazole-4-carboxylate；ethyl 2-oxo-3,4-diphenyl-1H-imidazole-5-carboxylate
• CAS: 501691-18-5
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: XSNKFEVCAXRRMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  237-238 °C(Solv: ethyl acetate (141-78-6))
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-oxo-1,5-diphenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid ethyl ester 在 sodium hydroxide 、 水 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 24.0h， 生成 2-oxo-1,5-diphenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  WO2008/89005

  摘要：

  公开号：
• 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 2-oxo-1,5-diphenyl-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

• 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。
• RENIN INHIBITORS
  申请人：Kwok Lily

  公开号：US20100105665A1

  公开（公告）日：2010-04-29

  Compounds, pharmaceutical compositions, kits, article of manufacture, methods of using, and method of preparing of compounds having the formula of: wherein the variables are as defined herein.

  化合物、药物组合物、试剂盒、制造物品、使用方法和制备方法，具有以下式子的化合物：其中变量的定义如下。
• Cyclic Amine Compound and Use Thereof for the Prophylaxis or Treatment of Hypertension
  申请人：Kuroita Takanobu

  公开号：US20100121048A1

  公开（公告）日：2010-05-13

  The present invention relates to a compound represented by the formula: (I) wherein ring A is a 5- or 6-membered aromatic heterocycle optionally having substituent (s); U, V and W are each independently C or N, provided that when any one of U, V and W is N, then the others should be C; Ra and Rb are each independently a cyclic group optionally having substituent(s), a C 1-10 alkyl group optionally having substituent(s), a C 2-10 alkenyl group optionally having substituent(s), or a C 2-10 alkynyl group optionally having substituent(s); X is a bond, or a spacer having 1 to 6 atoms in the main chain; Y is a spacer having 1 to 6 atoms in the main chain; Rc is a hydrocarbon group optionally containing heteroatom(s) as the constituting atom(s), which optionally has substituent(s); m and n are each independently 1 or 2; and ring B optionally further has substituent(s), or a salt thereof. The compound of the present invention has excellent renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.

  本发明涉及一种由式(I)表示的化合物：其中，环A是一种5或6成员的芳香杂环，可选地具有取代基；U、V和W分别独立地为C或N，但当U、V和W中的任何一个为N时，其他的应为C；Ra和Rb分别独立地为一个环状基团，可选地具有取代基；一个C1-10烷基，可选地具有取代基；一个C2-10烯基，可选地具有取代基；或一个C2-10炔基，可选地具有取代基；X是一条键或具有1到6个原子的主链间隔；Y是具有1到6个原子的主链间隔；Rc是一个含有杂原子作为构成原子的碳氢基团，可选地具有取代基；m和n分别独立地为1或2；环B可选地具有取代基，或其盐。本发明的化合物具有优异的肾素抑制活性，因此可用作预防或治疗高血压、高血压引起的各种器官损伤等的药物。
• US8148367B2
  申请人：——

  公开号：US8148367B2

  公开（公告）日：2012-04-03
• [EN] RENIN INHIBITORS<br/>[FR] INHIBITEURS DE RÉNINE
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2008089005A2

  公开（公告）日：2008-07-24

  [EN] Compounds, pharmaceutical compositions, kits, article of manufacture, methods of using, and method of preparing of compounds having the formula of : wherein the variables are as defined herein.
  [FR] L'invention concerne des composés, des compositions pharmaceutiques, des trousses, des articles de fabrication, des procédés d'utilisation, et des procédés de préparation de composés ayant la formule : dans laquelle les variables sont telles que définies ici.