3-ethyl-6-nitro-2-propylquinoline | 1383849-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-ethyl-6-nitro-2-propylquinoline
• CAS: 1383849-71-5
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: FZJSKKAIRJYLNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正丁醛 、 4-硝基苯胺 在 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 乙腈 为溶剂， 以53%的产率得到3-ethyl-6-nitro-2-propylquinoline
  参考文献：
  名称：

  在自由基阳离子诱导条件下由原位生成的亚胺及其烯胺互变异构体合成2,3-二取代喹啉

  摘要：

  在催化自由基阳离子盐诱导的条件下，实现了苯胺和醛的串联环化/芳构化，从而以高收率生产了一系列的2,3-二取代喹啉。在该反应中，原位生成的亚胺互变异构成烯胺，后者作为亲双烯体参与串联环化反应，进一步消除苯胺基引发四氢喹啉的芳构化，从而避免了恶劣的条件。

  DOI：

  10.1016/j.tetlet.2013.07.014

文献信息

• Oxidant Effect of H₂O₂for the Syntheses of Quinoline Derivatives via One-Pot Reaction of Aniline and Aldehyde
  作者：Qiaoxia Guo、Wennian Wang、Weiling Teng、Liwei Chen、Yanqing Wang、Baojian Shen

  DOI：10.1080/00397911.2011.563022

  日期：2012.9

  A convenient one-pot method for the synthesis of substituted quinolines via the reaction of aniline and aldehyde in the presence of a Lewis acid (AlCl3) and an oxidant (H2O2) has been developed. Hydrogen peroxide was found to promote the reaction by its function as a hydrogen hunter, hindering the formation of by-product N-alkylaniline. The effect of the oxidant on the yield and selectivity was studied. When the molar ratio of aniline, n-butyraldehyde, and H2O2 was 1:3:0.5 at 25 degrees C, the yield of 3-ethyl-2-propylquinoline was improved from 64% (reaction without H2O2) to 84% (with H2O2), and the quinoline selectivity was improved to almost 100%. Moreover, the reaction time was obviously reduced. The substituent effect was also investigated in this work.
• Synthesis of quinoline derivatives from anilines and aldehydes catalyzed by Cp 2 ZrCl 2 and recyclable Cp 2 ZrCl 2 /MCM-41 system
  作者：Qiaoxia Guo、Lijun Liao、Weiling Teng、Shenyong Ren、Xiao Wang、Yingying Lin、Fanfang Meng

  DOI：10.1016/j.cattod.2015.08.035

  日期：2016.4

  A facile method for the synthesis of quinoline derivatives using catalytic amount of Cp2ZrCl2 or Cp2ZrCl2 supported on MCM-41 (Cp2ZrCl2/MCM-41) in reaction of anilines and aldehydes is described. When Cp2ZrCl2/MCM-41 was used as catalyst, the yields of quinolines were enhanced by 5-15% compared with Cp2ZrCl2 as catalyst alone under the same reaction conditions. More importantly, Cp2ZrCl2/MCM-41 catalyst can be reused at least thrice by simple recover via filtration in air. Moreover, both Cp2ZrCl2 and Cp2ZrCl2/MCM-41 showed good catalytic activities to generate corresponding quinoline derivatives in moderate to good yields by varying the substituent of aniline and aldehyde. And the reaction conditions were optimized by studying the influences of reactant ratio, additives, solvent effect and reaction temperatures. (C) 2015 Elsevier B.V. All rights reserved.