ethyl 5,5-dimethyl-3-oxo-2-semicarbazono-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-1-carboxylate | 1128075-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: ethyl 5,5-dimethyl-3-oxo-2-semicarbazono-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-1-carboxylate
• CAS: 1128075-33-1
• 化学式: C₁₈H₂₀N₄O₄
• 分子量: 356.381
• InChiKey: IRPQIPOCSNNFEX-MOSHPQCFSA-N

物化性质

• 熔点：
  175-176 °C(Solvent: Benzene)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114.09
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  盐酸氨基脲 、 ethyl 2,3-dioxopyrrolo[2,1-a]isoquinoline-1-carboxylate 在 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 1.5h， 以85%的产率得到ethyl 5,5-dimethyl-3-oxo-2-semicarbazono-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-1-carboxylate
  参考文献：
  名称：

  Reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolinecarboxylic acid esters and amides with nitrogen-centered nucleophiles

  摘要：

  Reactions of ethyl 2,3-dioxopyrrolo[2,1-a]isoquinoline-1-carboxylates with active nitrogen-centered nucleophiles (phenylhydrazine, hydroxylamine, and benzylamine) involve opening of the pyrrole ring with formation of 2-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)-N'(1) ,N'(4)-diphenyl-3-(2-phenylhydrazono) succinohydrazide, 5-(6,7-dimethoxy-3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)-2,3,4,5-tetrahydro-1H-1,2-oxazine-3,4,6-trione, and ethyl 4-benzylamino-2-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)-3,4-dioxobutanoate, respectively. Cyclic amides derived from 5,5-dimethyl-2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-1-carboxylic acid react with benzylamine in a similar way. Reactions of the title compounds with weaker nucleophiles, such as semicarbazide and thiosemicarbazide, are not accompanied by opening of the pyrrole ring, and the products are the corresponding semicarbazones and thiosemicarbazones at the C-2=O carbonyl group.

  DOI：

  10.1134/s1070428008060109