1-butyl-5-(trifluoromethyl)-1,3-dihydrobenzoimidazol-2-one | 320407-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-butyl-5-(trifluoromethyl)-1,3-dihydrobenzoimidazol-2-one
• 英文别名: 1-butyl-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one；1-Butyl-5-trifluoromethyl-2,3-dihydro-1H-benzimidazol-2-one；1-Butyl-5-(trifluoromethyl)-1,3-dihydrobenzoimidazol-2-on；3-butyl-6-(trifluoromethyl)-1H-benzimidazol-2-one
• CAS: 320407-49-6
• 化学式: C₁₂H₁₃F₃N₂O
• 分子量: 258.243
• InChiKey: NAHAGSOZHTZHTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-bromo-4-trifluoromethylphenyl)-1-butylurea 在 copper(l) iodide 、 四甲基乙二胺 作用下， 以 水 为溶剂， 反应 15.0h， 以80%的产率得到1-butyl-5-(trifluoromethyl)-1,3-dihydrobenzoimidazol-2-one
  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

• [EN] BENZIMIDAZOLONE DERIVATIVES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] DERIVES DE BENZIMIDAZOLONE ET LEUR UTILISATION COMME INHIBITEURS DE LA PHOSPHODIESTERASE
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2001005770A1

  公开（公告）日：2001-01-25

  Compounds of formula (Ia) wherein Xa is CH or nitrogen, Ya is oxygen or sulfur, R?1a and R2a¿ are specific substituents, R?3a, R4a and R5a¿ are the same or different, hydrogen, halogen, cyano, lower alkoxy or lower-alkoxy-substituted aralkyl; or two of R?3a, R4a and R5a¿ may combine together to form lower alkylenedioxy, and m is 1 or 2, are useful as cGMP-PDE inhibitors.

  式(Ia)中的化合物，其中Xa为CH或氮，Ya为氧或硫，R1a和R2a是特定的取代基，R3a，R4a和R5a为相同或不同的氢，卤素，氰基，低烷氧基或低烷氧基取代的芳基甲基; 或者R3a，R4a和R5a中的两个可以结合形成低烷基二氧，m为1或2，可用作cGMP-PDE抑制剂。
• Synthesis of various 1‐alkylbenzimidazole derivatives directly from 2‐alkylaminonitroarenes via a two‐step, one‐pot procedure
  作者：Magdalena Walewska‐Królikiewicz、Bogdan Wilk、Andrzej Kwast、Zbigniew Wróbel

  DOI：10.1002/jhet.4830

  日期：2024.7

  anes, which were subjected, without isolation, to various cyclocondensation reactions with CS2, CO2, alkyl isocyanates, acyl chlorides, anhydrides, or esters. A simple, convenient, one-pot procedure provided derivatives of unsymmetrically substituted 1-alkylbenzimidazoles functionalized at C2 in good to excellent yields. The method does not require the use of metals, sensitive catalysts, or pressure

  N-烷基-2-硝基苯胺用三丁基膦脱氧形成中间体 2-(烷基氨基)芳基亚氨基正膦，无需分离即可与 CS 2 、CO 2 、烷基进行各种环缩合反应异氰酸酯、酰氯、酸酐或酯。一种简单、方便的一锅法以良好至优异的产率提供了在 C2 官能化的不对称取代的 1-烷基苯并咪唑的衍生物。该方法不需要使用金属、敏感催化剂或压力。
• BENZIMIDAZOLONE DERIVATIVES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1196391A1

  公开（公告）日：2002-04-17
• US6582351B1
  申请人：——

  公开号：US6582351B1

  公开（公告）日：2003-06-24