4-Amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile | 500264-39-1

• 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: 4-Amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile
• 英文别名: 4-amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile；4-amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-benzo[a]quinolizine-1,3-dicarbonitrile
• CAS: 500264-39-1
• 化学式: C₂₃H₂₀N₄O₂
• 分子量: 384.437
• InChiKey: KQKNEJKIUOJDDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile 、 原甲酸三乙酯 在 乙酸酐 作用下， 反应 5.0h， 以86%的产率得到ethyl N-(1,3-dicyano-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-benzo[a]quinolizin-4-yl)methanimidate
  参考文献：
  名称：

  Synthesis of Tetra- and Pentaheterocyclic Compounds Incorporated Isoquinoline Moiety

  摘要：

  7-Amino-2,3-dimethoxy-9-phenyl-5,6,9,6a-tetrahydropyridino[2,1-a]isoquinoline-8,10-dicarbonitrile 5 was prepared via Michael addition reaction of benzylidenemalononitrile 2 with isoquinoline-1-carbonitrile 1. Reaction of 5 with triethyl orthoformate and formamide led to the formation of the corresponding 4-ethoxymethylene and 4-aminopyrimidine derivatives of benzo[a]quinolizines 6 and 7, respectively. Compound 6 reacted with hydrazine to give imino-amino compound 8. The latter compound reacted with formic acid, triethyl orthoformate, acetic anhydride or benzoyl chloride to give the triazolopyrimidine derivatives 9, 10 and 11, respectively. Compound 8 reacted with hydrazonoyl halides 12, 13 and diethyl oxalate to give triazinopyrimidine and triazolopyrimidine derivatives 16, 17 and 20, respectively.

  DOI：

  10.3987/com-08-11481
• 作为产物：
  描述：

  苄烯丙二腈 、 (3,4-dihydro-6,7-dimethoxyisoquinolin-1-yl)acetonitrile 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以78%的产率得到4-Amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile
  参考文献：
  名称：

  Synthesis of Tetra- and Pentaheterocyclic Compounds Incorporated Isoquinoline Moiety

  摘要：

  7-Amino-2,3-dimethoxy-9-phenyl-5,6,9,6a-tetrahydropyridino[2,1-a]isoquinoline-8,10-dicarbonitrile 5 was prepared via Michael addition reaction of benzylidenemalononitrile 2 with isoquinoline-1-carbonitrile 1. Reaction of 5 with triethyl orthoformate and formamide led to the formation of the corresponding 4-ethoxymethylene and 4-aminopyrimidine derivatives of benzo[a]quinolizines 6 and 7, respectively. Compound 6 reacted with hydrazine to give imino-amino compound 8. The latter compound reacted with formic acid, triethyl orthoformate, acetic anhydride or benzoyl chloride to give the triazolopyrimidine derivatives 9, 10 and 11, respectively. Compound 8 reacted with hydrazonoyl halides 12, 13 and diethyl oxalate to give triazinopyrimidine and triazolopyrimidine derivatives 16, 17 and 20, respectively.

  DOI：

  10.3987/com-08-11481