methyl 3-(methoxycarbonyl)-9-methyl-7-phenyl-7H-pyrazolo[3,4-h][1,6]naphthyridin-2-acetate | 1280127-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: methyl 3-(methoxycarbonyl)-9-methyl-7-phenyl-7H-pyrazolo[3,4-h][1,6]naphthyridin-2-acetate
• 英文别名: Methyl 3-(methoxycarbonyl)-9-methyl-7-phenyl-7h-pyrazolo[3,4-h][1,6]naphthyridin-2-acetate；methyl 2-(2-methoxy-2-oxoethyl)-9-methyl-7-phenylpyrazolo[3,4-h][1,6]naphthyridine-3-carboxylate
• CAS: 1280127-62-9
• 化学式: C₂₁H₁₈N₄O₄
• 分子量: 390.398
• InChiKey: VWDHOVVUGIXOOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 4-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以62%的产率得到methyl 3-(methoxycarbonyl)-9-methyl-7-phenyl-7H-pyrazolo[3,4-h][1,6]naphthyridin-2-acetate
  参考文献：
  名称：

  Synthetic utility of a heterocyclic o-aminoaldehyde: synthesis of pyrazolopyridopyrimidines, pyrazolonaphthyridines, and pyrazolopyrimidonaphthyridinones

  摘要：

  A series of various polysubstituted pyrazolo[3,4-h][1,6]naphthyridines, benzo[b]pyrazolo[3,4-h][1,6]naphthyridines, and pyrazolo[4',3':5,6]pyrido[4,3-d]pyrimidines were synthesized by Friedlander condensation of 4-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (o-aminoaldehyde) with active methylene compounds. The o-aminoaldehyde was functionalized to o-aminonitrile and o-aminocarboxamide with malononitrile and cyanoacetamide, respectively, which on condensation with monosubstituted ureas and acetic anhydride, respectively, afforded pyrazolo[3,4-h]pyrimido[4,5-b][1,6]naphthyridines.

  DOI：

  10.1007/s00706-010-0443-9

文献信息

• Synthetic utility of a heterocyclic o-aminoaldehyde: synthesis of pyrazolopyridopyrimidines, pyrazolonaphthyridines, and pyrazolopyrimidonaphthyridinones
  作者：Sandeep M. Bagul、Dilip R. Birari、Maruti G. Ghagare、Raghunath B. Toche、Madhukar N. Jachak

  DOI：10.1007/s00706-010-0443-9

  日期：2011.2

  A series of various polysubstituted pyrazolo[3,4-h][1,6]naphthyridines, benzo[b]pyrazolo[3,4-h][1,6]naphthyridines, and pyrazolo[4',3':5,6]pyrido[4,3-d]pyrimidines were synthesized by Friedlander condensation of 4-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (o-aminoaldehyde) with active methylene compounds. The o-aminoaldehyde was functionalized to o-aminonitrile and o-aminocarboxamide with malononitrile and cyanoacetamide, respectively, which on condensation with monosubstituted ureas and acetic anhydride, respectively, afforded pyrazolo[3,4-h]pyrimido[4,5-b][1,6]naphthyridines.