10,12-dibromo-6,8,13,13a-tetrahydro-5H-isoquinolino[1,2-b]quinazoline | 1429206-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 10,12-dibromo-6,8,13,13a-tetrahydro-5H-isoquinolino[1,2-b]quinazoline
• CAS: 1429206-47-2
• 化学式: C₁₆H₁₄Br₂N₂
• 分子量: 394.109
• InChiKey: SVYOEBWKBXXCMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氢异喹啉 、 2-氨基-3,5-二溴苯甲醛 以 乙醇 为溶剂， 反应 16.0h， 以96%的产率得到10,12-dibromo-6,8,13,13a-tetrahydro-5H-isoquinolino[1,2-b]quinazoline
  参考文献：
  名称：

  Metal-Free α-Amination of Secondary Amines: Computational and Experimental Evidence for Azaquinone Methide and Azomethine Ylide Intermediates

  摘要：

  We have performed a combined computational and experimental study to elucidate the mechanism of a metal-free alpha-amination of secondary amines. Calculations predicted azaquinone methides and azomethine ylides as the reactive intermediates and showed that iminium ions are unlikely to participate in these transformations. These results were confirmed by experimental deuterium-labeling studies and the successful trapping of the postulated azomethine ylide and azaquinone methide intermediates. In addition, computed barrier heights for the rate-limiting step correlate qualitatively with experimental findings.

  DOI：

  10.1021/jo400483h

文献信息

• Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with o-Aminobenzaldehydes: Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone, and Ruteacarpine
  作者：Daniel Seidel、Matthew Richers、Indubhusan Deb、Alena Platonova、Chen Zhang

  DOI：10.1055/s-0033-1338852

  日期：——

  Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine alpha-amination/N-alkylation. This unique alpha-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.
• Metal-Free α-Amination of Secondary Amines: Computational and Experimental Evidence for Azaquinone Methide and Azomethine Ylide Intermediates
  作者：Arne Dieckmann、Matthew T. Richers、Alena Yu. Platonova、Chen Zhang、Daniel Seidel、K. N. Houk

  DOI：10.1021/jo400483h

  日期：2013.4.19

  We have performed a combined computational and experimental study to elucidate the mechanism of a metal-free alpha-amination of secondary amines. Calculations predicted azaquinone methides and azomethine ylides as the reactive intermediates and showed that iminium ions are unlikely to participate in these transformations. These results were confirmed by experimental deuterium-labeling studies and the successful trapping of the postulated azomethine ylide and azaquinone methide intermediates. In addition, computed barrier heights for the rate-limiting step correlate qualitatively with experimental findings.