7,8-dimethoxy-3H-2-benzazepine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7,8-dimethoxy-3H-2-benzazepine
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: MIFIJSYNRLLRPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴藜芦醛 、 (Z)-3-(tributylstannyl)allylamine 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以18%的产率得到7,8-dimethoxy-3H-2-benzazepine
  参考文献：
  名称：

  An efficient synthesis of substituted (Z)-allylamines and 7-membered nitrogen heterocycles from (Z)-3-(tributylstannyl)allylamine

  摘要：

  The reaction of N-(trimethylsilyl)allylamine with 2 mol of n-butyllithium, followed by treatment with chlorotributyltin and subsequent hydrolysis, gave (Z)-3-(tributylstannyl)allylamines in high yields. The N,N-disilylated derivatives, upon transmetalation of the C-Sn bond, led to unstable vinyllithium species. The latter readily underwent a [1,4] nitrogen to carbon silyl migration to give a lithium amide. The unprotected (Z)-3-(tributylstannyl)allylamine underwent a palladium-catalyzed cross-coupling reaction with aromatic bromides affording a stereospecific preparation of substituted allylic amines with Z configuration of the carbon-carbon double bond. The reactions of ortho-functionalized aryl bromides offer a one-step preparation of 7-membered nitrogen heterocycles in high yields.

  DOI：

  10.1021/jo00058a026

文献信息

• An efficient synthesis of substituted (Z)-allylamines and 7-membered nitrogen heterocycles from (Z)-3-(tributylstannyl)allylamine
  作者：Robert J. P. Corriu、Bolin Geng、Joel J. E. Moreau

  DOI：10.1021/jo00058a026

  日期：1993.3

  The reaction of N-(trimethylsilyl)allylamine with 2 mol of n-butyllithium, followed by treatment with chlorotributyltin and subsequent hydrolysis, gave (Z)-3-(tributylstannyl)allylamines in high yields. The N,N-disilylated derivatives, upon transmetalation of the C-Sn bond, led to unstable vinyllithium species. The latter readily underwent a [1,4] nitrogen to carbon silyl migration to give a lithium amide. The unprotected (Z)-3-(tributylstannyl)allylamine underwent a palladium-catalyzed cross-coupling reaction with aromatic bromides affording a stereospecific preparation of substituted allylic amines with Z configuration of the carbon-carbon double bond. The reactions of ortho-functionalized aryl bromides offer a one-step preparation of 7-membered nitrogen heterocycles in high yields.