1-(4-氟苄基)-1H-苯并[d]咪唑-2(3H)-酮 | 100460-87-5

• 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-氟苄基)-1H-苯并[d]咪唑-2(3H)-酮
• 英文名称: 1-<(4-fluorophenyl)methyl>-benzimidazol-2(3H)-one
• 英文别名: 1-(4-fluorobenzyl)-1,3-dihydrobenzoimidazol-2-one；1-(4-fluorobenzyl)-1H-benzo[d]imidazol-2(3H)-one；1-(4-fluorobenzyl)-1,3-dihydro-2H-benzimidazol-2-one；3-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-one
• CAS: 100460-87-5
• 化学式: C₁₄H₁₁FN₂O
• mdl: MFCD03821190
• 分子量: 242.253
• InChiKey: SOGFCHRGTJVMRX-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C(Solv: hexane (110-54-3))
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氟苄基)-1H-苯并[d]咪唑-2(3H)-酮 在 氢溴酸 、 sodium hydride 、 potassium iodide 、 三氯氧磷 作用下， 反应 33.5h， 生成 阿司咪唑
  参考文献：
  名称：

  A Short Synthesis of Astemizole

  摘要：

  The synthesis of astemizole 6, a potent H-1-antihistaminic agent, was achieved in 20 % overall yield. Compound 6 was obtained in high purity and on a multigram scale starting from 2-hydroxybenzimidazole.

  DOI：

  10.1080/00397919608004642
• 作为产物：
  描述：

  N-(4''-fluorobenzyl)-2-nitroaniline 在 palladium on activated charcoal 氢气 、 calcium chloride 作用下， 以 甲醇 、 xylene 为溶剂， 反应 23.5h， 生成 1-(4-氟苄基)-1H-苯并[d]咪唑-2(3H)-酮
  参考文献：
  名称：

  Eine neue Synthese von 1-Alkyl-1,3-dihydro-2H-benzimidazol-2-onen

  摘要：

  DOI：

  10.1007/bf00798789

文献信息

• 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.
• Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi
  作者：Sangmi Oh、Sungbum Kim、Sunju Kong、Gyongseon Yang、Nakyung Lee、Dawoon Han、Junghyun Goo、Jair L. Siqueira-Neto、Lucio H. Freitas-Junior、Rita Song

  DOI：10.1016/j.ejmech.2014.07.038

  日期：2014.9

  A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.
• Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones
  作者：Nekane Barbero、Mónica Carril、Raul SanMartin、Esther Domínguez

  DOI：10.1016/j.tet.2008.05.072

  日期：2008.7

  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.
• Properly tuned first fluoride-catalyzed TGME-mediated amination process for chloroimidazoles: inexpensive technology for antihistaminic norastemizole
  作者：Chris H. Senanayake、Yaping Hong、Tingjian Xiang、H.Scott Wilkinson、Roger P. Bakale、Alex R. Jurgens、Mark F. Pippert、Hal T. Butler、Stephen A. Wald

  DOI：10.1016/s0040-4039(99)01350-7

  日期：1999.9

  Fluoride-catalyzed amination process of chloroimidazole 1 proved to be a practical and inexpensive procedure for the preparation of the antihistaminic, norastemizole. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Copper-Catalyzed Intramolecular Cyclization to N-Substituted 1,3-Dihydrobenzimidazol-2-ones
  作者：Zhaoguang Li、Hongbin Sun、Hualiang Jiang、Hong Liu

  DOI：10.1021/ol8011106

  日期：2008.8.7

  An efficient and convenient method was developed for preparing N-substituted 1,3-dihydrobenzimidazol-2-ones from N'-substituted N-(2-halophenyl)ureas via a Cul/DBU-catalyzed cyclization in DMSO under microwave heating. High yields were obtained and a variety of functional groups were tolerated under these conditions, including N'-aryl, alkyl, heterocyclic, various N-(substituted 2-halophenyl) and N-(2-iodopyridyl)ureas.