(E)-methyl-3-methoxy-5-(3-(N-(methoxycarbonyl)-4-methylphenylsulfonamido)prop-1-enyl)-2-(trifluoromethylsulfonyloxy)benzoate | 1176891-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-methyl-3-methoxy-5-(3-(N-(methoxycarbonyl)-4-methylphenylsulfonamido)prop-1-enyl)-2-(trifluoromethylsulfonyloxy)benzoate
• 英文别名: methyl 3-methoxy-5-[(E)-3-[methoxycarbonyl-(4-methylphenyl)sulfonylamino]prop-1-enyl]-2-(trifluoromethylsulfonyloxy)benzoate
• CAS: 1176891-07-8
• 化学式: C₂₂H₂₂F₃NO₁₀S₂
• 分子量: 581.545
• InChiKey: GCASMKVCKGIBOC-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  methyl 5-allyl-3-methoxy-2-(trifluoromethylsulfonyloxy)benzoate 、 甲苯磺酰氨基甲酸甲酯 在 air 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 N,N-二异丙基乙胺 、 对苯醌 作用下， 以 甲基叔丁基醚 为溶剂， 反应 72.0h， 以89%的产率得到(E)-methyl-3-methoxy-5-(3-(N-(methoxycarbonyl)-4-methylphenylsulfonamido)prop-1-enyl)-2-(trifluoromethylsulfonyloxy)benzoate
  参考文献：
  名称：

  A Catalytic, Brønsted Base Strategy for Intermolecular Allylic C−H Amination

  摘要：

  A Bronsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.

  DOI：

  10.1021/ja903939k

文献信息

• A Catalytic, Brønsted Base Strategy for Intermolecular Allylic C−H Amination
  作者：Sean A. Reed、Anthony R. Mazzotti、M. Christina White

  DOI：10.1021/ja903939k

  日期：2009.8.26

  A Bronsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.