3-benzyl-2-methylquinoline

• 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-benzyl-2-methylquinoline
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: IHXLTTGASCITSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  在 铁粉 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以85%的产率得到3-benzyl-2-methylquinoline
  参考文献：
  名称：

  Iron/acetic acid-mediated carbon degradation: a facile route for the synthesis of quinoline derivatives

  摘要：

  A new carbon degradation protocol which results in the formation of quinoline derivatives is described. The reactions involved the use of mild reaction conditions and an inexpensive reducing reagent (Fe/AcOH). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.063

文献信息

• Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis
  作者：Chan Sik Cho、Bok Tae Kim、Tae-Jeong Kim、Sang Chul Shim

  DOI：10.1039/b109245f

  日期：2001.12.19

  2-Aminobenzyl alcohol is oxidatively cyclised with an array of ketones in dioxane at 80 °C in the presence of a catalytic amount of a ruthenium catalyst and KOH to afford the corresponding quinolines in high yields.

  2-氨基苯甲醇在80°C下，在二恶烷中与一系列酮进行氧化性环化反应，此时在催化量的钌催化剂和氢氧化钾的存在下，以高产率得到相应的喹啉化合物。
• A recyclable palladium-catalyzed modified Friedländer quinoline synthesis
  作者：Chan Sik Cho、Wen Xiu Ren

  DOI：10.1016/j.jorganchem.2007.06.022

  日期：2007.9

  2-Aminobenzyl alcohol reacts with an array of ketones in toluene/poly(ethylene glycol) (PEG-2000) at 100 °C in the presence of a palladium catalyst along with KOH under an atmosphere of air to give the corresponding quinolines in good yields. The catalytic system could be recovered and reused five times without any loss of catalytic activity.

  2-氨基苄醇在钯催化剂和KOH的存在下，在空气气氛下于100°C在甲苯/聚乙二醇（PEG-2000）中与一系列酮反应，以高收率得到相应的喹啉。该催化体系可以被回收并重复使用五次，而不会损失任何催化活性。
• A copper(II)-catalyzed protocol for modified Friedländer quinoline synthesis
  作者：Chan Sik Cho、Wen Xiu Ren、Sang Chul Shim

  DOI：10.1016/j.tetlet.2006.07.067

  日期：2006.9

  2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl2 along with KOH under O2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl2 and KOH

  2-氨基苄醇在O 2气氛下，在催化量的CuCl 2和KOH的存在下，在100°C的条件下与一系列酮在二恶烷中反应，以高收率提供相应的喹啉。还通过逐步操作步骤将2-氨基苄醇氧化偶联并与各种醛环化，在CuCl 2和KOH存在下于O 2气氛下于二恶烷中对2-氨基苄醇进行初始处理，然后将醛添加至混合物，然后在氩气气氛下搅拌，以中等至良好的产率得到3-取代的喹啉。
• Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines
  作者：Chan Sik Cho、Bok Tae Kim、Heung-Jin Choi、Tae-Jeong Kim、Sang Chul Shim

  DOI：10.1016/j.tet.2003.08.027

  日期：2003.9

  2-Aminobenzyl alcohol is oxidatively coupled and cyclized with secondary alcohols in dioxane at 80°C in the presence of a catalytic amount of RuCl2(PPh3)3 and KOH along with 1-dodecene as a sacrificial hydrogen acceptor to give the corresponding quinolines in good yields. The cyclization is applicable to a wide range of alkyl(aryl) and alkyl(alkyl) carbinols. The catalytic pathway seems to be proceeded

  在催化量的RuCl 2（PPh 3）3和KOH以及1-十二碳烯作为牺牲氢受体的情况下，在80°C下于二恶烷中氧化2-氨基苄醇并与仲醇环化，得到相应的喹啉丰产。环化适用于广泛的烷基（芳基）和烷基（烷基）甲醇。催化途径似乎是通过以下顺序进行的：涉及两种底物的初始氧化成羰基化合物，醛醇缩合反应和环脱水。
• An approach for quinolines via palladium-catalyzed Heck coupling followed by cyclization
  作者：Chan Sik Cho、Jun Uk Kim

  DOI：10.1016/j.tetlet.2007.04.001

  日期：2007.5

  2-Iodoaniline reacts with alpha,beta-unsaturated carbonyl compounds in DMF at 100 degrees C in the presence of a catalytic amount of a palladium catalyst along with a base to afford the corresponding quinolones or quinolines in moderate to good yields. (C) 2007 Elsevier Ltd. All rights reserved.