2-(2-Cyclopropylethynyl)-4-fluorobenzaldehyde | 1207290-11-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-Cyclopropylethynyl)-4-fluorobenzaldehyde
• CAS: 1207290-11-6
• 化学式: C₁₂H₉FO
• 分子量: 188.201
• InChiKey: UMFVEIZVMMSJHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Cyclopropylethynyl)-4-fluorobenzaldehyde 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.67h， 生成 5-cyclopropyl-1-ethyl-8-fluoropyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Copper(II)-Catalyzed Oxidation of an Aliphatic C−H Bond of Tertiary Amine in Air

  摘要：

  A multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and tertiary amine is discovered, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good yields under mild conditions. In the reaction process, silver(I)-catalyzed intramolecular cyclization and copper(II)-catalyzed oxidation of an aliphatic C-H bond of tertiary amine in air are involved.

  DOI：

  10.1021/ol102939r

文献信息

• Silver triflate-catalyzed three-component reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and α,β-unsaturated carbonyl compound
  作者：Shengqing Ye、Xiaodi Yang、Jie Wu

  DOI：10.1039/c0cc00905a

  日期：——

  A highly efficient silver triflate-catalyzed three-component reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and alpha,beta-unsaturated carbonyl compound is reported, which affords H-pyrazolo[5,1-a]isoquinoline-1-carboxylates in good yield.

  报道了高效的三氟甲磺酸银催化的2-炔基苯甲醛，磺酰肼和α，β-不饱和羰基化合物的三组分反应，可提供高收率的H-吡唑并[5,1-a]异喹啉-1-羧酸酯。
• Synthesis of 1-(1<i>H</i>-Indol-3-yl)-1,2-dihydroisoquinolines via AgOTf-Catalyzed Three-Component Reactions of 2-Alkynylbenzaldehydes, Amines, and Indoles
  作者：Xingxin Yu、Jie Wu

  DOI：10.1021/cc9001263

  日期：2010.3.8

  Three-component reactions of 2-alkynylbenzaldehydes, amines, and indoles catalyzed by AgOTf Under mild conditions afford the 1-(1H-indol-3-yl)-1,1-dihydroisoquinolines in good yields. This silver-catalyzed tandem reaction is found to be workable with various indoles. anilines or alkyl amines, and 2-alkynylbenzaldehydes with electron-withdrawing groups attached oil the aromatic backbone.
• An efficient route to diverse H-pyrazolo[5,1-a]isoquinolines via sequential multi-component/cross-coupling reactions
  作者：Xingxin Yu、Xiaolin Pan、Jie Wu

  DOI：10.1016/j.tet.2010.12.005

  日期：2011.2

  Multi-component reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, electrophile (bromine or iodine), and ketone or aldehyde under mild conditions proceeds smoothly to afford the functionalized H-pyrazolo[5,1-a]isoquinolines in good yields. This one-pot process involves intermolecular condensation, electrophilic cyclization, nucleophilic addition, intramolecular condensation, and aromatization. The resulting halo-containing H-pyrazolo[5,1-a]isoquinolines could be further elaborated via palladium-catalyzed cross-coupling reactions. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.