6-fluoro-3-(4-methoxyphenyl)-1H-benzimidazol-2-one

• 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: 6-fluoro-3-(4-methoxyphenyl)-1H-benzimidazol-2-one
• 化学式: C₁₄H₁₁FN₂O₂
• 分子量: 258.252
• InChiKey: ZBMRQNHQPOQMHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47.02
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-甲氧基苯脲 、 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， 生成 6-fluoro-3-(4-methoxyphenyl)-1H-benzimidazol-2-one 、 甲氧苯胺 、 对甲氧基苯异氰酸酯
  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.