N-2-methyl-but-3-enoyl-(N-2-methyl-prop-2-enyl)-tolylsulfonamide

• 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: N-2-methyl-but-3-enoyl-(N-2-methyl-prop-2-enyl)-tolylsulfonamide
• 英文别名: 3-methyl-N-(4-methylphenyl)sulfonyl-N-(2-methylprop-2-enyl)but-3-enamide
• 化学式: C₁₆H₂₁NO₃S
• 分子量: 307.414
• InChiKey: LOIOGNWVAOYFQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  烯丙基三丁基锡 、 对甲基苯磺酰异氰酸酯 、 3-氯-2-甲基丙烯 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以71%的产率得到N-2-methyl-but-3-enoyl-(N-2-methyl-prop-2-enyl)-tolylsulfonamide
  参考文献：
  名称：

  Palladium-Catalyzed Tandem Bis-allylation of Isocyanates

  摘要：

  [GRPAHICS]A tandem bis-allylation of p-toluenesulfonyl isocyanate can be achieved by palladium-catalyzed three-component coupling reaction with allylstannanes and allyl chlorides, A high level of regioselectivity can be obtained by the appropriate choice of the allylic substituents. The reaction mechanism and the regiochemistry of the reaction can be explained by formation of an amphoteric bis-allylpalladium intermediate, This bis-allylpalladium intermediate undergoes an initial electrophilic attack on one of the allyl moieties followed by a nucleophilic attack on the other.

  DOI：

  10.1021/ol015545s

文献信息

• Palladium-Catalyzed Tandem Bis-allylation of Isocyanates
  作者：Niclas Solin、Sanjay Narayan、Kálmán J. Szabó

  DOI：10.1021/ol015545s

  日期：2001.3.1

  [GRPAHICS]A tandem bis-allylation of p-toluenesulfonyl isocyanate can be achieved by palladium-catalyzed three-component coupling reaction with allylstannanes and allyl chlorides, A high level of regioselectivity can be obtained by the appropriate choice of the allylic substituents. The reaction mechanism and the regiochemistry of the reaction can be explained by formation of an amphoteric bis-allylpalladium intermediate, This bis-allylpalladium intermediate undergoes an initial electrophilic attack on one of the allyl moieties followed by a nucleophilic attack on the other.