Butyl-(2-methoxy-phenyl)-methyl-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Butyl-(2-methoxy-phenyl)-methyl-amine
• 英文别名: N-butyl-2-methoxy-N-methylaniline
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: OYEBUUDUEJERHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻苯二甲醚 、 正丁胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 N-丁基-N-(2-甲氧基苯基)胺 、 Butyl-(2-methoxy-phenyl)-methyl-amine
  参考文献：
  名称：

  Direct substitution of aromatic ethers by lithium amides. A new aromatic amination reaction

  摘要：

  Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution. Especially with lithiated secondary amines high conversions and selectivities are achieved. Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates. The scope and mechanistic implications of this novel nucleophilic amination reaction are described.

  DOI：

  10.1021/jo00071a019

文献信息

• Direct substitution of aromatic ethers by lithium amides. A new aromatic amination reaction
  作者：Wolter ten Hoeve、Chris G. Kruse、Jan M. Luteyn、Janet R. G. Thiecke、Hans Wynberg

  DOI：10.1021/jo00071a019

  日期：1993.9

  Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution. Especially with lithiated secondary amines high conversions and selectivities are achieved. Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates. The scope and mechanistic implications of this novel nucleophilic amination reaction are described.