5-fluoro-1-(4-fluorophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one | 1537547-35-5

• 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: 5-fluoro-1-(4-fluorophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one
• 英文别名: 6-fluoro-3-(4-fluorophenyl)-1H-benzimidazol-2-one
• CAS: 1537547-35-5
• 化学式: C₁₃H₈F₂N₂O
• 分子量: 246.216
• InChiKey: WVLXWCDCXHELQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 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：
  3

反应信息

• 作为产物：
  描述：

  4-氟苯脲 、 2-溴-1-氯-4-氟苯 在 potassium phosphate 、 BrettPhos precatalyst 作用下， 以 叔丁醇 为溶剂， 反应 14.0h， 以59%的产率得到5-fluoro-1-(4-fluorophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one
  参考文献：
  名称：

  Regioselective Synthesis of Benzimidazolones via Cascade C–N Coupling of Monosubstituted Ureas

  摘要：

  A direct method for the regioselective construction of benzimidazolones is reported wherein a single palladium catalyst is employed to couple monosubstituted urea substrates with differentially substituted 1,2-dihaloaromatic systems. In this method, the catalyst is able to promote a cascade of two discrete chemoselective C-N bond-forming processes that allows the highly selective and predictable formation of complex heterocycles from simple, readily available starting materials.

  DOI：

  10.1021/ol501531q

文献信息

• Regioselective Synthesis of Benzimidazolones via Cascade C–N Coupling of Monosubstituted Ureas
  作者：Johannes B. Ernst、Nicholas E. S. Tay、Nathan T. Jui、Stephen L. Buchwald

  DOI：10.1021/ol501531q

  日期：2014.7.18

  A direct method for the regioselective construction of benzimidazolones is reported wherein a single palladium catalyst is employed to couple monosubstituted urea substrates with differentially substituted 1,2-dihaloaromatic systems. In this method, the catalyst is able to promote a cascade of two discrete chemoselective C-N bond-forming processes that allows the highly selective and predictable formation of complex heterocycles from simple, readily available starting materials.