(Z)-6-[2-cyano-1-(3-fluorophenyl)ethenyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine

• 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: (Z)-6-[2-cyano-1-(3-fluorophenyl)ethenyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine
• 英文别名: (Z)-3-(2-amino-3-propan-2-ylsulfonylbenzimidazol-5-yl)-3-(3-fluorophenyl)prop-2-enenitrile
• 化学式: C₁₉H₁₇FN₄O₂S
• 分子量: 384.434
• InChiKey: JCACBOHBEQKUSH-LZYBPNLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氰化钠 、 6-[(Z)-2-Bromo-1-(3-fluoro-phenyl)-vinyl]-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine 在 四(三苯基膦)钯 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到(Z)-6-[2-cyano-1-(3-fluorophenyl)ethenyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine
  参考文献：
  名称：

  Cooperative Catalyst Effects in Palladium-Mediated Cyanation Reactions of Aryl Halides and Triflates

  摘要：

  Substoichiometric quantities of copper or zinc species dramatically improve both conversion rate and efficiency of Pd(0)-catalyzed cyanation reactions. The optimum reaction conditions involve the use of a nitrile solvent, NaCN, and a catalyst system employing the combination of cuprous iodide with tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)(4)]. Beneficial effects were observed for the conversion of aryl halides, aryl triflates, and a vinyl bromide to the corresponding nitriles. The process was demonstrated on preparative scale with a broad range of aromatic and heteroaromatic substrates containing diverse functionality. A dual catalytic cycle is proposed to explain the profound influences of the cocatalyst system.

  DOI：

  10.1021/jo9808674