2-amino-7,7-dimethyl-5-oxo-4-phenyl-1-(4H-1,2,4-triazol-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-amino-7,7-dimethyl-5-oxo-4-phenyl-1-(4H-1,2,4-triazol-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 2-amino-7,7-dimethyl-5-oxo-4-phenyl-1-(1H-1,2,4-triazol-5-yl)-6,8-dihydro-4H-quinoline-3-carbonitrile
• 化学式: C₂₀H₂₀N₆O
• 分子量: 360.418
• InChiKey: NRGXTDBLDKCQKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-7,7-dimethyl-5-oxo-4-phenyl-1-(4H-1,2,4-triazol-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 、 乙酸酐 反应 3.0h， 以82%的产率得到2,8,8-trimethyl-5-phenyl-10-(4H-1,2,4-triazol-3-yl)-5,8,9,10-tetrahydropyrimido[4,5-b]quinoline-4,6(3H,7H)-dione
  参考文献：
  名称：

  β-烯胺酮高效合成 1-(4H-1,2,4-Triazol-3-yl)-Hexahydroquinoline-3-carbonitrile 及其螺衍生物

  摘要：

  A series of N-((1,2,4-triazol-3-yl)-enamine and N-((1,2,3-triazol-4-yl)-enamine were prepared and reacted with a alpha,beta-unsaturated nitriles to yield novel N-(4H-1,2,4-triazol-3-yl)hexahydroquinoline-3-carbonitriles and their fused and Spiro derivatives. Dimroth type rearrangement of the prepared quinoline derivatives 7a,b and 15a,b was observed in acetic anhydride leading to the formation of substituted pyrimido[4,5-b]quinolines 11a,b, spiro[indoline-3,5'-pyrimido [4,5-b]quinoline] 19 and spiro [indoline-3,5'-[1,3]-oxazino[4,5-b]quinoline] 22.

  DOI：

  10.3987/com-15-13353
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 哌啶 、 三氯乙酸 作用下， 以 乙醇 为溶剂， 反应 3.33h， 生成 2-amino-7,7-dimethyl-5-oxo-4-phenyl-1-(4H-1,2,4-triazol-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  β-烯胺酮高效合成 1-(4H-1,2,4-Triazol-3-yl)-Hexahydroquinoline-3-carbonitrile 及其螺衍生物

  摘要：

  A series of N-((1,2,4-triazol-3-yl)-enamine and N-((1,2,3-triazol-4-yl)-enamine were prepared and reacted with a alpha,beta-unsaturated nitriles to yield novel N-(4H-1,2,4-triazol-3-yl)hexahydroquinoline-3-carbonitriles and their fused and Spiro derivatives. Dimroth type rearrangement of the prepared quinoline derivatives 7a,b and 15a,b was observed in acetic anhydride leading to the formation of substituted pyrimido[4,5-b]quinolines 11a,b, spiro[indoline-3,5'-pyrimido [4,5-b]quinoline] 19 and spiro [indoline-3,5'-[1,3]-oxazino[4,5-b]quinoline] 22.

  DOI：

  10.3987/com-15-13353