1-methyl-2,4,6-trioxospiro(perhydropyrimidino-5,5'-(5',6',6a',7',8',9',10',11'-octahydroazepino[1,2-a]quinoline)) | 1242594-49-5

• 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: 1-methyl-2,4,6-trioxospiro(perhydropyrimidino-5,5'-(5',6',6a',7',8',9',10',11'-octahydroazepino[1,2-a]quinoline))
• CAS: 1242594-49-5
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: NLYGSKPADHAAAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-甲基巴比妥酸 、 2-(azepan-1-yl)benzaldehyde 以 乙醇 为溶剂， 反应 1.08h， 以84%的产率得到1-methyl-2,4,6-trioxospiro(perhydropyrimidino-5,5'-(5',6',6a',7',8',9',10',11'-octahydroazepino[1,2-a]quinoline))
  参考文献：
  名称：

  Diastereoselective synthesis of 1-alkyl-2,4,6-trioxoperhydropyrimidine-5-spiro-3′-(1′,2′,3′,4′-tetrahydroquinolines)

  摘要：

  Knoevenagel products formed by the condensation of N-monoalkyl barbituric acids with o-tert-amino benzaldehydes undergo tert-amino effect reactions (T-reactions) yielding 1-alkyl-2,4,6-trioxoperhydropyrimidine-5-spiro-3'-(1',2',3',4'-tetrahydroquinoline) derivatives as a mixture of (S*,S*)- and (S*,R*)-diastereomers. Mostly, the major diastereomer has the S*,S*-configuration. According to X-ray diffraction data in the solid form and NOE data in solution, diastereoselectivity of the T-reactions can be associated with the structure of the Knoevenagel products whose conformation is fixed by the strong intramolecular C-H center dot center dot center dot pi interaction. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.015