5,7-dibromo-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline | 1004781-27-4

• 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: 5,7-dibromo-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline
• CAS: 1004781-27-4
• 化学式: C₁₁H₁₂Br₂N₂
• 分子量: 332.038
• InChiKey: IEIIPCGRKSJIFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,7-dibromo-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline 在 叔丁基过氧化氢 、 potassium iodide 、 哌啶 作用下， 以 癸烷 、 乙醇 为溶剂， 反应 37.0h， 以88%的产率得到5,7-dibromo-2,3-dihydro[2,1-b]quinazoline-9-(1H)-one
  参考文献：
  名称：

  选择性乙酸铜(II)和碘化钾催化缩醛胺氧化为二氢喹唑啉和喹唑啉酮生物碱。

  摘要：

  乙酸铜(II)/乙酸/O2 和碘化钾/叔丁基过氧化氢体系分别影响稠环缩醛胺选择性氧化为二氢喹唑啉和喹唑啉酮。这些方法使得能够容易地制备多种喹唑啉生物碱天然产物及其类似物。

  DOI：

  10.3762/bjoc.9.135
• 作为产物：
  描述：

  2-氨基-3,5-二溴苯甲醛 以 乙醇 、 正丁醇 为溶剂， 反应 0.67h， 生成 5,7-dibromo-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline
  参考文献：
  名称：

  Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with o-Aminobenzaldehydes: Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone, and Ruteacarpine

  摘要：

  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.

  DOI：

  10.1055/s-0033-1338852

文献信息

• α-Amination of Nitrogen Heterocycles:  Ring-Fused Aminals
  作者：Chen Zhang、Chandra Kanta De、Rudrajit Mal、Daniel Seidel

  DOI：10.1021/ja077473r

  日期：2008.1.1

  Aromatic aminoaldehydes react with cyclic amines to produce ring-fused aminals under thermal conditions. This process applied to two-step syntheses of the quinazolinone alkaloids deoxyvasicinone and rutaecarpine.
• 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.
• Ring-fused aminals: catalyst and solvent-free microwave-assisted α-amination of nitrogen heterocycles
  作者：Vivek Polshettiwar、Rajender S. Varma

  DOI：10.1016/j.tetlet.2008.09.166

  日期：2008.12

  A high-yield synthesis of ring-fused aminals via microwave (MW)-assisted alpha-amination of nitrogen heterocycles at 130 degrees C under solvent- and catalyst-free conditions is described. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• Selective copper(II) acetate and potassium iodide catalyzed oxidation of aminals to dihydroquinazoline and quinazolinone alkaloids
  作者：Matthew T Richers、Chenfei Zhao、Daniel Seidel

  DOI：10.3762/bjoc.9.135

  日期：——

  acetate/acetic acid/O2 and potassium iodide/tert-butylhydroperoxide systems are shown to affect the selective oxidation of ring-fused aminals to dihydroquinazolines and quinazolinones, respectively. These methods enable the facile preparation of a number of quinazoline alkaloid natural products and their analogues.

  乙酸铜(II)/乙酸/O2 和碘化钾/叔丁基过氧化氢体系分别影响稠环缩醛胺选择性氧化为二氢喹唑啉和喹唑啉酮。这些方法使得能够容易地制备多种喹唑啉生物碱天然产物及其类似物。