(E)-N-(4-cinnamylphenyl)-4-methylbenzenesulfonamide | 1411604-97-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-N-(4-cinnamylphenyl)-4-methylbenzenesulfonamide
• 英文别名: 4-methyl-N-[4-[(E)-3-phenylprop-2-enyl]phenyl]benzenesulfonamide
• CAS: 1411604-97-1
• 化学式: C₂₂H₂₁NO₂S
• 分子量: 363.48
• InChiKey: ARNSNDBZHGOSRA-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酸肉桂酯 、 N-(4-碘苯基)-4-甲基苯磺酰胺 在 N-乙基-2-吡咯烷酮 、 氯化镍二甲氧基乙烷 、 4,4',4''-三叔丁基2,2',6'2''-曲吡啶 、 锌 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(E)-N-(4-cinnamylphenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Selective Cross-Coupling of Organic Halides with Allylic Acetates

  摘要：

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

  DOI：

  10.1021/jo302086g

文献信息

• Selective Cross-Coupling of Organic Halides with Allylic Acetates
  作者：Lukiana L. Anka-Lufford、Michael R. Prinsell、Daniel J. Weix

  DOI：10.1021/jo302086g

  日期：2012.11.16

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.