1-(4-氯苯基)-1,3-二氢-2H-苯并咪唑-2-酮 | 19920-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-(4-氯苯基)-1,3-二氢-2H-苯并咪唑-2-酮
• 英文名称: 1-(4-chlorophenyl)-1,3-dihydrobenzoimidazol-2-one
• 英文别名: 1-(4-chlorophenyl)-1,3-dihydro-2H-benzoimidazol-2-one；1-(p-Chlor-phenyl)-2-benzimidazolinon；N-(p-Chlor-phenyl)-benzimidazolin-2-on；1-(4-chlorophenyl)-1,3-dihydro-2H-benzimidazol-2-one；1-(4-Chlorophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one；3-(4-chlorophenyl)-1H-benzimidazol-2-one
• CAS: 19920-11-7
• 化学式: C₁₃H₉ClN₂O
• 分子量: 244.68
• InChiKey: BOXURPJZEYMGEC-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208 °C(Solv: hexane (110-54-3))
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-1,3-二氢-2H-苯并咪唑-2-酮 在 苯膦酰二氯 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 {[1-(4-chlorophenyl)-1,3-dihydro-2H-benzimidazol-2-ylidene]-hydrazono}-(2-furyl)acetic acid
  参考文献：
  名称：

  3-Aryl-[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one: A Novel Template for the Design of Highly Selective A_2B Adenosine Receptor Antagonists

  摘要：

  In an effort to identify novel ligands possessing high affinity and selectivity for the A(2B) AR subtype, we further investigated the class of 3-aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones V, previously disclosed by us as selective A(1) AR antagonists. Preliminary assays on a number of triazinobenzimidazoles derived from our "in-house" collection revealed that all the derivatives selected showed significant affinity at A(2B) AR, no affinity at A(3) AR, and various degrees of selectivity toward A(1) and A(2A) ARs. Investigation of a new series featuring modified substituents at the 10-position (4'-chlorophenyl or phenylethyl groups), and a chlorine atom at the 7-position (X) of the triazinobenzimidazole nucleus, yielded highly potent and selective A(2B) AR antagonists. The presence of a pendant 3-phenyl ring appears to hamper the interaction with A(2A) AR, conferring high A(2B)/A(2A) AR selectivity. Derivative 13 (X = Cl, R = C6H5) is the most potent and selective compound, with an IC50 of 3.10 nM at A(2B) AR and no affinity at A(1), A(2A), and A(3) ARs.

  DOI：

  10.1021/jm201177b
• 作为产物：
  描述：

  1-(2-溴苯基)-1-(4-氯苯基)脲 在 copper(l) iodide 、 四甲基乙二胺 作用下， 以 水 为溶剂， 反应 15.0h， 以57%的产率得到1-(4-氯苯基)-1,3-二氢-2H-苯并咪唑-2-酮
  参考文献：
  名称：

  Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones

  摘要：

  The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of Cut and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.072

文献信息

• Selenium‐Catalyzed Carbonylative Synthesis of 2‐Benzimidazolones from 2‐Nitroanilines with TFBen as the CO Source
  作者：Xinxin Qi、Rong Zhou、Jin‐Bao Peng、Jun Ying、Xiao‐Feng Wu

  DOI：10.1002/ejoc.201801739

  日期：2019.9

  A selenium‐catalyzed carbonylative reaction for the synthesis of 2‐benzimidazolones from 2‐nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene‐1,3,5‐triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2‐benzimidazolones were produced in moderate to excellent yields.

  已开发了一种硒催化的羰基化反应，用于从2-硝基苯胺合成2-苯并咪唑酮。在此策略中，为避免使用有毒的CO气体，TFBen（苯-1,3,5-三甲酸酯三甲酸酯）被用作固体和稳定的CO前体，并且生产了各种所需的2-苯并咪唑酮，其中中等至极好。产量。
• Discovery of novel, orally available benzimidazoles as melanin concentrating hormone receptor 1 (MCHR1) antagonists
  作者：Pradip K. Sasmal、Sanjita Sasmal、P. Tirumala Rao、B. Venkatesham、M. Roshaiah、Chandrasekhar Abbineni、Ish Khanna、Vikram P. Jadhav、J. Suresh、Rashmi Talwar、Syed Muzeeb、Jean-Marie Receveur、Thomas M. Frimurer、Øystein Rist、Lisbeth Elster、Thomas Högberg

  DOI：10.1016/j.bmcl.2010.07.086

  日期：2010.9

  Melanin concentrating hormone (MCH) is an important mediator of energy homeostasis and plays role in several disorders such as obesity, stress, depression and anxiety. The synthesis and biological evaluation of novel benzimidazole derivatives as MCHR1 antagonists are described. The in vivo proof of principle for weight loss with a lead compound from this series is exemplified. (c) 2010 Elsevier Ltd. All rights reserved.
• FUSED CYCLIC UREA DERIVATIVES AS CRHR2 ANTAGONIST
  申请人：RaQualia Pharma Inc.

  公开号：US20210078975A1

  公开（公告）日：2021-03-18

  The present invention relates to fused cyclic urea derivatives which have antagonistic activities against CRHR1 and/or CRHR2, and which are useful in the treatment or prevention of disorders and diseases in which CRHR1 and/or CRHR2 is involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CRHR1 and/or CRHR2 is involved.