5-cyclopropylpyrazolo[5,1-a]isoquinoline | 1400575-48-5

• 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: 5-cyclopropylpyrazolo[5,1-a]isoquinoline
• CAS: 1400575-48-5
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: QFJPYQSUQAAVDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙醇 、 N'-(2-(cyclopropylethynyl)benzylidene)-4-methylbenzenesulfonohydrazide 在 silver trifluoromethanesulfonate 、 氧气 、 potassium carbonate 、 palladium dichloride 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以90%的产率得到5-cyclopropylpyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  三氟甲磺酸银-氯化钯协同催化串联反应合成H-吡唑并[5,1- a ]异喹啉

  摘要：

  AbstractA tandem reaction of N′‐(2‐alkynylbenzylidene)hydrazone with alcohol in the presence of oxygen co‐catalyzed by silver triflate and palladium chloride under mild conditions is reported, providing H‐pyrazolo[5,1‐a]isoquinolines in good yields. During the transformation, isoquinolinium‐2‐yl amide was the key intermediate via a silver(I)‐catalyzed 6‐endo cyclization of N′‐(2‐alkynylbenzylidene)hydrazone. The presence of a palladium catalyst and molecular oxygen promoted the oxidation of the alcohol to the aldehyde or ketone. Subsequent nucleophilic attack of the in situ generated enolate to isoquinolinium‐2‐yl amide, intramolecular condensation, and aromatization afforded the H‐pyrazolo[5,1‐a]isoquinolines. The easily available starting materials, good substrate generality, mild reaction conditions, and experimental ease should make this method attractive for further library construction.magnified image

  DOI：

  10.1002/adsc.201300327