5,5-Dimethyl-1-(piperidine-1-carbonyl)-2H,3H,5H,6H-pyrrolo[2,1-A]isoquinoline-2,3-dione | 131527-19-0

• 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: 5,5-Dimethyl-1-(piperidine-1-carbonyl)-2H,3H,5H,6H-pyrrolo[2,1-A]isoquinoline-2,3-dione
• 英文别名: 5,5-dimethyl-1-(piperidine-1-carbonyl)-6H-pyrrolo[2,1-a]isoquinoline-2,3-dione
• CAS: 131527-19-0
• 化学式: C₂₀H₂₂N₂O₃
• mdl: MFCD00608572
• 分子量: 338.406
• InChiKey: RTEQYHPEWQWVDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  5,5-Dimethyl-1-(piperidine-1-carbonyl)-2H,3H,5H,6H-pyrrolo[2,1-A]isoquinoline-2,3-dione 在 氨 作用下， 以 苯 为溶剂， 反应 0.08h， 以86%的产率得到(3E)-3-(3,3-dimethyl-2,4-dihydroisoquinolin-1-ylidene)-2,4-dioxo-4-piperidin-1-ylbutanamide
  参考文献：
  名称：

  2,3-二氧杂吡咯并[2,1-a]异喹啉与氨和脂肪胺的反应

  摘要：

  DOI：

  10.1023/b:cohc.0000048291.71402.3b
• 作为产物：
  描述：

  草酰氯 、 2-[3,3-Dimethyl-3,4-dihydro-2H-isoquinolin-(1Z)-ylidene]-1-piperidin-1-yl-ethanone 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以76%的产率得到5,5-Dimethyl-1-(piperidine-1-carbonyl)-2H,3H,5H,6H-pyrrolo[2,1-A]isoquinoline-2,3-dione
  参考文献：
  名称：

  2,3-二氧杂吡咯并[2,1-a]异喹啉与邻苯二胺的反应

  摘要：

  DOI：

  10.1007/bf00756422

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.
• Allylboration of isatin and 2,3-dioxopyrrolo[2,1-a]isoquinolines
  作者：A. G. Mikhailovskii、A. V. Ignatenko、Yu. N. Bubnov

  DOI：10.1007/bf02251683

  日期：1998.7
• Synthesis of isoquinoline derivatives of quinoxalin-2-one from pyrrolo[2,1-a]isoquinoline-2,3-diones and o-phenylenediamine
  作者：O. V. Surikova、Z. G. Aliev、N. N. Polygalova、A. G. Mikhailovskii、M. I. Vakhrin

  DOI：10.1134/s1070428008060201

  日期：2008.6

  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.
• Synthesis of 2-spiro-(1,2-dihydroperimid-2-yl)-5,5-dialkyl-2,3,5,6-tetrahydropyrrolo[2,1-a]-isoquinolin-3-ones
  作者：O. V. Surikova、Z. G. Aliev、A. G. Mikhailovskii

  DOI：10.1007/s10593-009-0207-9

  日期：2008.12

  2,3-Dioxpyrrolo[2,1-a]isoquinolines react with 1,8-naphthalenediamine in 2-propanol in the presence of p-toluenesulfonic acid to give 2-spiro-(1,2-dihydroperimid-2-yl)-5,5-dialkyl-2,3,5,6-tetrahydro-pyrrolo[2,1-a]isoquinolin-3-ones whose structure was confirmed by X-ray analysis.
• Reaction of pyrrolo[2,1-a]isoquinoline-2,3-diones with carbon-centered nucleophiles
  作者：O. V. Surikova、A. G. Mikhailovskii、N. N. Polygalova、M. I. Vakhrin

  DOI：10.1134/s1070428008060110

  日期：2008.6

  Knoevenagel condensations of 5,5-dimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-diones with malononitrile, ethyl cyanoacetate, indan-1,3-dione, and Drotaverine base involved the ketone carbonyl group in the former with formation of deeply colored dark blue substances. The lactam ring in the products can be opened by the action of nitrogen-centered nucleophiles, e.g., p-toluidine. The reaction of 5,5-dimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-dione with methyl magnesium iodide gave 2-hydroxy-2,5,5-trimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinolin-3-one.