ethyl 2,3-dioxopyrrolo[2,1-a]isoquinoline-1-carboxylate | 163769-82-2

• 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 2,3-dioxopyrrolo[2,1-a]isoquinoline-1-carboxylate
• 英文别名: Ethyl 5,5-dimethyl-2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-1-carboxylate；ethyl 5,5-dimethyl-2,3-dioxo-6H-pyrrolo[2,1-a]isoquinoline-1-carboxylate
• CAS: 163769-82-2
• 化学式: C₁₇H₁₇NO₄
• mdl: MFCD00404528
• 分子量: 299.326
• InChiKey: IXOSQPZYAZZOMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-dioxopyrrolo[2,1-a]isoquinoline-1-carboxylate 在 一水合肼 作用下， 以 异丙醇 为溶剂， 以76%的产率得到4-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-iden)hexahydropyridazin-3,5,6-trione
  参考文献：
  名称：

  Reactions of 2,3-Dioxopyrrolo[2,1-a]isoquinolines with Active N-Nucleophiles

  摘要：

  DOI：

  10.1007/s10593-005-0299-9
• 作为产物：
  描述：

  草酰氯 、 ethyl (3,3-dimethyl-1,2,3,4-tetrahydro-1-isoquinolylidene)acetate 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 2.33h， 以87%的产率得到ethyl 2,3-dioxopyrrolo[2,1-a]isoquinoline-1-carboxylate
  参考文献：
  名称：

  Reaction of enamines of the isocholine and phenanthridine series with oxalyl chloride

  摘要：

  DOI：

  10.1007/bf01169639

文献信息

• Reaction of 2,3-dioxopyrrolo[2,1-a]iso-quinolines with binucleophiles
  作者：O. V. Surikova、A. G. Mikhailovskii、M. I. Vakhrin

  DOI：10.1007/s10593-009-0396-2

  日期：2009.9

  1-a]isoquinolines with binucleophiles such as 2-amino-4-methyl-phenol, o-aminothiophenol, and caprolactam hydrazidine proceeds with opening of the dioxopyrroline ring and is accompanied by heterocyclization to give heteroaromatic benzoxazole, benzothiazole, and 1,2,4-triazole systems. Heterocyclization does not occur in the reaction of o-hydroxybenzylamine, o-aminobenzyl alcohol, and the hydrazide of anthranilic

  2，3-二氧杂吡咯并[2，1- a ]异喹啉与双亲核试剂如2-氨基-4-甲基苯酚，邻氨基硫代苯酚和己内酰胺肼的反应随着二氧杂吡咯啉环的打开而进行，并伴随杂环化为得到杂芳族苯并恶唑，苯并噻唑和1,2,4-三唑体系。在邻羟基苄胺，邻氨基苄醇和邻氨基苯甲酸酰肼的反应中不会发生杂环化。形成相应的线性N-苄基酰胺，苄基酯和二酰肼产物。
• 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.
• Synthesis of pyrrolo[2,1-a]isoquinoline hydrazones and oximes
  作者：A. G. Mikhaflovskii、V. S. Shklyaev、A. V. Ignatenko、M. I. Vakhrin

  DOI：10.1007/bf01170741

  日期：1995.7
• 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
• Reaction of enamines of the isocholine and phenanthridine series with oxalyl chloride
  作者：A. G. Mikhailovskii、V. S. Shklyaev

  DOI：10.1007/bf01169639

  日期：1994.7