1-ethyl-5-phenylpyrazolo[5,1-a]isoquinoline | 1221497-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-ethyl-5-phenylpyrazolo[5,1-a]isoquinoline
• 英文别名: 1-Ethyl-5-phenylpyrazolo[5,1-a]isoquinoline
• CAS: 1221497-62-6
• 化学式: C₁₉H₁₆N₂
• 分子量: 272.349
• InChiKey: TXKSQFYLXXJCQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-phenylethynylbenzaldehyde p-toluenesulphonylhydrazone 、 正丁胺 在 silver trifluoromethanesulfonate 、 palladium(II) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以55%的产率得到1-ethyl-5-phenylpyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Palladium-catalyzed oxidation of amine in air: an efficient approach to H-pyrazolo[5,1-a]-isoquinolines

  摘要：

  An efficient approach to H-pyrazolo[5,1-a]isoquinolines through a reaction of N'-(2-alkynylbenzylidene) hydrazide with amine in the presence of a cooperative catalysis under mild conditions is reported. The palladium-catalyzed oxidation of amine in air leading to the formation of enamine is the key step during the transformation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.066

文献信息

• Tandem Reactions of <i>N</i>′-(2-Alkynylbenzylidene)hydrazides with Silyl Enolates: A Facile Route to <i>H</i>-Pyrazolo[5,1-<i>a</i>]isoquinolines
  作者：Xingxin Yu、Zhiyuan Chen、Xiaodi Yang、Jie Wu

  DOI：10.1021/cc1000314

  日期：2010.5.10

  A silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with silyl enolate is described, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good to excellent yields. Intramolecular cyclization, nucleophilic addition, condensation, and aromatization may be involved in the reaction process.

  描述了N '-（2-炔基亚苄基）酰肼与烯丙基甲硅烷基酯的三氟甲磺酸银催化串联反应，可产生出人意料的H-吡唑并[5,1- a ]异喹啉，收率高至优异。反应过程中可能涉及分子内环化，亲核加成，缩合和芳构化。
• Synthesis of H-pyrazolo[5,1-a]isoquinolines via a silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alcohol
  作者：Wenyan Hao、Tinli Zhang、Mingzhong Cai

  DOI：10.1016/j.tet.2013.08.049

  日期：2013.11

  A silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alcohol is reported, which generates H-pyrazolo[5,1-a]isoquinoline derivatives in good yields under mild conditions.

  的三氟甲磺酸银催化的串联反应Ñ ' - （2- alkynylbenzylidene）与醇酰肼报道，其产生ħ -吡唑并[5,1-一个在温和的条件下良好的产率]异喹啉衍生物。
• Silver Triflate-Palladium Chloride Cooperative Catalysis in a Tandem Reaction for the Synthesis of<i>H</i>-Pyrazolo[5,1-<i>a</i>]isoquinolines
  作者：Qing Xiao、Jie Sheng、Qiuping Ding、Jie Wu

  DOI：10.1002/adsc.201300327

  日期：2013.8.12

  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
• Facile Assembly of <i>H</i> ‐Pyrazolo[5,1‐ <i>a</i> ]isoquinolines <i>via</i> Silver Triflate‐Catalyzed One‐Pot Tandem Reaction of 2‐Alkynyl‐ benzaldehyde, Sulfonohydrazide, and Ketone or Aldehyde
  作者：Xingxin Yu、Shengqing Ye、Jie Wu

  DOI：10.1002/adsc.201000176

  日期：2010.10.9

  AbstractA novel and efficient route for the generation of H‐pyrazolo[5,1‐a]isoquinolines via silver triflate‐catalyzed one‐pot tandem reaction of 2‐alkynylbenzaldehyde, sulfonohydrazide, and ketone or aldehyde is described. This reaction proceeds with good functional group tolerance under mild conditions with high efficiency and excellent selectivity.
• Palladium-catalyzed oxidation of amine in air: an efficient approach to H-pyrazolo[5,1-a]-isoquinolines
  作者：Jie Sheng、Ying Guo、Jie Wu

  DOI：10.1016/j.tet.2013.05.066

  日期：2013.8

  An efficient approach to H-pyrazolo[5,1-a]isoquinolines through a reaction of N'-(2-alkynylbenzylidene) hydrazide with amine in the presence of a cooperative catalysis under mild conditions is reported. The palladium-catalyzed oxidation of amine in air leading to the formation of enamine is the key step during the transformation. (C) 2013 Elsevier Ltd. All rights reserved.