1-ethyl-9-fluoro-5-phenylpyrazolo[5,1-a]isoquinoline | 1221497-66-0

• 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-9-fluoro-5-phenylpyrazolo[5,1-a]isoquinoline
• CAS: 1221497-66-0
• 化学式: C₁₉H₁₅FN₂
• 分子量: 290.34
• InChiKey: YQSJUSVYROWCEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 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：
  2

反应信息

• 作为产物：
  描述：

  N'-(5-fluoro-2-(phenylethynyl)benzylidene)-4-methylbenzenesulfonohydrazide 、 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76%的产率得到1-ethyl-9-fluoro-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。
• 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.