1-(Azepane-1-carbonyl)-5,5-dimethyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-2,3-dione

• 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: 1-(Azepane-1-carbonyl)-5,5-dimethyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-2,3-dione
• 英文别名: 1-(Azepan-1-ylcarbonyl)-5,5-dimethyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-2,3-dione；1-(azepane-1-carbonyl)-5,5-dimethyl-6H-pyrrolo[2,1-a]isoquinoline-2,3-dione
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: IAKJVKZVEXJAHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Azepane-1-carbonyl)-5,5-dimethyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-2,3-dione 、 邻苯二胺 在 对甲苯磺酸 作用下， 以 异丙醇 为溶剂， 以82%的产率得到3-[2-(azepan-1-yl)-1-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)-2-oxoethyl]quinoxalin-2(1H)-one
  参考文献：
  名称：

  Synthesis of isoquinoline derivatives of quinoxalin-2-one from pyrrolo[2,1-a]isoquinoline-2,3-diones and o-phenylenediamine

  摘要：

  Reactions of 5,5-dialkyl-2,3,4,5-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-diones with o-phenylenediamine in the presence of a catalytic amount of hydrogen chloride or p-toluenesulfonic acid involved opening of the pyrrole ring with formation of 3-(3,3-dialkyl-1,2,3,4-tetrahydroisoquinolin-1-ylidenemethyl)quinoxalin-2(1H)-ones. The presence of an enamine fragment in the products was confirmed by reaction with oxalyl chloride.

  DOI：

  10.1134/s1070428008060201

文献信息

• Reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolinecarboxylic acid esters and amides with nitrogen-centered nucleophiles
  作者：O. V. Surikova、A. G. Mikhailovskii、N. N. Polygalova、M. I. Vakhrin

  DOI：10.1134/s1070428008060109

  日期：2008.6

  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.
• Reactions of 2,3-Dioxopyrrolo[2,1-a]isoquinolines with Ammonia and Aliphatic Amines
  作者：A. G. Mikhailovskii、N. N. Polygalova、T. S. Turova、G. A. Lobashova、M. I. Vahrin

  DOI：10.1023/b:cohc.0000048291.71402.3b

  日期：2004.9