6,8-Dimethyl-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline-5-carbonitrile | 1004781-19-4

• 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: 6,8-Dimethyl-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline-5-carbonitrile
• 英文别名: 6,8-dimethyl-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline-5-carbonitrile
• CAS: 1004781-19-4
• 化学式: C₁₄H₁₇N₃
• 分子量: 227.309
• InChiKey: YZAYVRSFFPDVDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 2-Amino-3-formyl-4,6-dimethylbenzonitrile 以 乙醇 为溶剂， 反应 18.0h， 以95%的产率得到6,8-Dimethyl-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazoline-5-carbonitrile
  参考文献：
  名称：

  α-Amination of Nitrogen Heterocycles:  Ring-Fused Aminals

  摘要：

  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.

  DOI：

  10.1021/ja077473r

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.
• 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.