5,5-Dimethyl-1-(phenylcarbonyl)-5,6-dihydropyrrolo[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: 5,5-Dimethyl-1-(phenylcarbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2,3-dione
• 英文别名: 1-benzoyl-5,5-dimethyl-6H-pyrrolo[2,1-a]isoquinoline-2,3-dione
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: XZJRGNYNZRQETM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.4
• 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-(phenylcarbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2,3-dione 在 hydrazine hydrate 作用下， 以 异丙醇 为溶剂， 以60%的产率得到(3Z)-3-[3,3-dimethyl-3,4-dihydroisoquinolin-1-(2H)-ylidene]-2,4-dioxo-4-phenylbutanehydrazide
  参考文献：
  名称：

  Synthesis and properties of 1-aroyl-5,5-dialkyl-2,3,5,6-tetrahydropyrrolo[ 2,1-a]isoquinoline-2,3-diones

  摘要：

  Acylation of 1-methyl-3,3-dialkyl-3,4-dihydroisoquinolines with acid chlorides afforded enaminoketones. Enaminophenylketones from the obtained series were reacted with oxalyl chloride to provide 1-benzoyl-5,5-dialkyl-2,3,5,6- tetrahydropyrrolo[2,1-a]isoquinoline- 2,3-diones. The reaction of the latter with binucleophiles leads to the opening of the pyrrole ring and to the heterocyclization: Under the effect of o-phenyldiamine qinoxaline is formed, 1,2-cyclohexanediamine provides the hexahydro-benzimidazole system, D3/4-aminophenol gives benzoxazole, 3-hydroxy-2-amino-pyridine furnishes oxazolo[4,5-b]pyridine. In the reaction with hydrazine hydrate the acylation occurs with hydrazide formation.

  DOI：

  10.1134/s1070428016020111
• 作为产物：
  描述：

  1,3,3-三甲基-3,4-二氢异喹啉 在 三乙胺 作用下， 生成 5,5-Dimethyl-1-(phenylcarbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2,3-dione
  参考文献：
  名称：

  Synthesis and properties of 1-aroyl-5,5-dialkyl-2,3,5,6-tetrahydropyrrolo[ 2,1-a]isoquinoline-2,3-diones

  摘要：

  Acylation of 1-methyl-3,3-dialkyl-3,4-dihydroisoquinolines with acid chlorides afforded enaminoketones. Enaminophenylketones from the obtained series were reacted with oxalyl chloride to provide 1-benzoyl-5,5-dialkyl-2,3,5,6- tetrahydropyrrolo[2,1-a]isoquinoline- 2,3-diones. The reaction of the latter with binucleophiles leads to the opening of the pyrrole ring and to the heterocyclization: Under the effect of o-phenyldiamine qinoxaline is formed, 1,2-cyclohexanediamine provides the hexahydro-benzimidazole system, D3/4-aminophenol gives benzoxazole, 3-hydroxy-2-amino-pyridine furnishes oxazolo[4,5-b]pyridine. In the reaction with hydrazine hydrate the acylation occurs with hydrazide formation.

  DOI：

  10.1134/s1070428016020111

文献信息

• 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
• Synthesis and properties of 1-aroyl-5,5-dialkyl-2,3,5,6-tetrahydropyrrolo[ 2,1-a]isoquinoline-2,3-diones
  作者：A. G. Mikhailovskii、A. S. Yusov、O. V. Gashkova

  DOI：10.1134/s1070428016020111

  日期：2016.2

  Acylation of 1-methyl-3,3-dialkyl-3,4-dihydroisoquinolines with acid chlorides afforded enaminoketones. Enaminophenylketones from the obtained series were reacted with oxalyl chloride to provide 1-benzoyl-5,5-dialkyl-2,3,5,6- tetrahydropyrrolo[2,1-a]isoquinoline- 2,3-diones. The reaction of the latter with binucleophiles leads to the opening of the pyrrole ring and to the heterocyclization: Under the effect of o-phenyldiamine qinoxaline is formed, 1,2-cyclohexanediamine provides the hexahydro-benzimidazole system, D3/4-aminophenol gives benzoxazole, 3-hydroxy-2-amino-pyridine furnishes oxazolo[4,5-b]pyridine. In the reaction with hydrazine hydrate the acylation occurs with hydrazide formation.