2-heptyl-3-hexylquinoline

• 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: 2-heptyl-3-hexylquinoline
• 化学式: C₂₂H₃₃N
• 分子量: 311.511
• InChiKey: RMABAFZHDCULBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正辛醛 、 苯胺 在 二氯二茂锆 作用下， 以 二氯甲烷 为溶剂， 以39%的产率得到2-heptyl-3-hexylquinoline
  参考文献：
  名称：

  Synthesis of quinoline derivatives from anilines and aldehydes catalyzed by Cp 2 ZrCl 2 and recyclable Cp 2 ZrCl 2 /MCM-41 system

  摘要：

  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.

  DOI：

  10.1016/j.cattod.2015.08.035

文献信息

• Ruthenium-catalyzed formal alkyl group transfer: Synthesis of quinolines from nitroarenes and alkylammonium halides
  作者：Chan Sik Cho、Na Young Lee、Tae-Jeong Kim、Sang Chul Shim

  DOI：10.1002/jhet.5570410320

  日期：2004.5

  Nitroarenes are reductively cyclized with an array of tetraalkylammonium halides and trialkylarnmonium chlorides in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride dihydrate at 180° to afford the corresponding quinolines in moderate to good yields. The addition of tin(II) chloride dihydrate is necessary for the effective formation of quinolines and toluene is

  在催化量的钌催化剂和二水合氯化锡（II）的存在下，将四烷基卤化铵和三烷基氯化铵与硝基芳烃进行还原性环合，在180°下产生适量至良好收率的相应喹啉。为了有效形成喹啉，必须添加二水合氯化锡（II），甲苯是选择的溶剂。针对该催化过程，提出了一种反应途径，该反应途径包括首先将硝基芳烃还原为苯胺，然后将烷基铵卤化物转化为烷基胺，将烷基从烷基胺转移至苯胺以形成亚胺，使亚胺二聚，并进行杂环化。
• Oxygen-implanted MoS₂ nanosheets promoting quinoline synthesis from nitroarenes and aliphatic alcohols <i>via</i> an integrated oxidation transfer hydrogenation–cyclization mechanism
  作者：Chaofeng Zhang、Zhuyan Gao、Puning Ren、Jianmin Lu、Zhipeng Huang、Kaiyi Su、Shichao Zhang、Junju Mu、Feng Wang

  DOI：10.1039/d1gc04058h

  日期：——

  with oxygen-implanting modification (O-MoS2) can work as a multifunctional catalyst to achieve the one-pot quinoline synthesis from basic nitroarenes and aliphatic alcohols. Different from common knowledge that the application of MoS2-based catalysts and above quinoline synthesis need anaerobic conditions, we conduct the heterogeneous catalysis under an unusual air atmosphere. Catalyst characterization

  我们在此报告了具有氧注入修饰的MoS 2 (O-MoS 2 )可以作为多功能催化剂来实现从碱性硝基芳烃和脂肪醇的一锅法合成喹啉。不同于众所周知的MoS 2基催化剂的应用及以上喹啉合成需要厌氧条件，我们在不寻常的空气气氛下进行多相催化。催化剂表征和实验结果表明，嵌入在 MoS 2骨架中的 MoO x簇，而不是配位不饱和 Mo 位点 (CUS Mo)，主导了喹啉的生成。通过颠覆 MoS 上 O 2吸附的催化认识x可以使用一种有效的方法来原位修复 O-MoS 2中的 MoO x结构通过用额外的 H* 抑制不需要的 MoO x消除来保护 O-MoS 2催化剂，从而使基于 MoS 2的催化剂失活，我们创新地引入了 O 2成喹啉合成。坚固的 O-MoS 2无需再生即可连续使用 10 次，从硝基苯和乙醇中提取 2-甲基喹啉的收率可达 69-75%。此外，与传统的转移氢化-缩合机理不同，在O-MoS 2上
• 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.