2-methylpyrazolo[5,1-a]isoquinoline-5-carbaldehyde | 1621622-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-methylpyrazolo[5,1-a]isoquinoline-5-carbaldehyde
• CAS: 1621622-92-1
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: ZOCGXJQAWZRZIU-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methylpyrazolo[5,1-a]isoquinoline-5-carbaldehyde 、 ((1-methyl-4-phenyl-1H-imidazol-2-yl)methyl)triphenylphosphonium chloride 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以0.168 g的产率得到2-methyl-5-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)vinyl)pyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Synthesis and SAR study of novel tricyclic pyrazoles as potent phosphodiesterase 10A inhibitors

  摘要：

  Novel pyrazolo[5,1-f][1,6]naphthyridines, pyrazolo[5,1-a][2,6]naphthyridines, pyrazolo[5,1-a][2,7]naphthyridines and pyrazolo[5,1-a]isoquinolines phenylimidazole/benzimidazole ethylene-linked were designed and synthesized for PDE10A interaction. An AgOTf and proline-cocatalyzed multicomponent methodology based on use of o-alkynylaldehydes, tosylhydrazide and ketones was developed and proved to be a convenient route for assembly of most of the novel tricyclic pyrazoles synthesized. Pyrazolo[5,1-f][1,6]naphthyridine 43 and 59, pyrazolo[5,1-a][2,6]naphthyridine 66, and pyrazolo[5,1-a][2,7]naphthyridine 42 showed the highest affinity for PDE10A enzyme (IC50 = 40, 42, 40, 55 nM, respectively).

  DOI：

  10.1016/j.ejmech.2014.07.020
• 作为产物：
  描述：

  (2-methylpyrazolo[5,1-a]isoquinolin-5-yl)methanol 在 戴斯-马丁氧化剂 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 2-methylpyrazolo[5,1-a]isoquinoline-5-carbaldehyde
  参考文献：
  名称：

  Synthesis and SAR study of novel tricyclic pyrazoles as potent phosphodiesterase 10A inhibitors

  摘要：

  Novel pyrazolo[5,1-f][1,6]naphthyridines, pyrazolo[5,1-a][2,6]naphthyridines, pyrazolo[5,1-a][2,7]naphthyridines and pyrazolo[5,1-a]isoquinolines phenylimidazole/benzimidazole ethylene-linked were designed and synthesized for PDE10A interaction. An AgOTf and proline-cocatalyzed multicomponent methodology based on use of o-alkynylaldehydes, tosylhydrazide and ketones was developed and proved to be a convenient route for assembly of most of the novel tricyclic pyrazoles synthesized. Pyrazolo[5,1-f][1,6]naphthyridine 43 and 59, pyrazolo[5,1-a][2,6]naphthyridine 66, and pyrazolo[5,1-a][2,7]naphthyridine 42 showed the highest affinity for PDE10A enzyme (IC50 = 40, 42, 40, 55 nM, respectively).

  DOI：

  10.1016/j.ejmech.2014.07.020