2-benzyl-7-methoxy-3-phenylquinoline

• 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-benzyl-7-methoxy-3-phenylquinoline
• 英文别名: 2-Benzyl-7-methoxy-3-phenylquinoline
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: CIINLTZMEPUVKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 间氨基苯甲醚 在 2,2,6,6-四甲基哌啶氧化物 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到2-benzyl-7-methoxy-3-phenylquinoline
  参考文献：
  名称：

  Sc（OTf）3-介导的苯胺和环氧化物一锅合成2,3-二取代喹啉。

  摘要：

  在这里，我们报道了由苯胺和芳香族或脂肪族环氧化物首次合成2,3-二取代喹啉。该反应利用Sc（OTf）3作为路易斯酸和使用TEMPO作为除氧剂。以中等至极好的收率（高达96％）获得了各种高度取代的喹啉。

  DOI：

  10.1021/acs.joc.0c00803

文献信息

• Amination of Aromatic Olefins with Anilines: A New Domino Synthesis of Quinolines
  作者：Matthias Beller、Oliver R. Thiel、Harald Trauthwein、Christian G. Hartung

  DOI：10.1002/1521-3765(20000717)6:14<2513::aid-chem2513>3.0.co;2-v

  日期：2000.7.17

  A new catalytic amination of aromatic olefins with anilines is presented. In a domino reaction, substituted quinoline derivatives are obtained in the presence of cationic rhodium complexes, such as [Rh(cod)2]BF4, and PPh3. Ethylbenzene is formed as a by-product in this new oxidative reaction. The first transition metal catalyzed anti-Markovnikov hydroamination of styrene with anilines occurs as a side

  提出了一种新的苯胺催化芳香族烯烃的胺化方法。在多米诺反应中，在阳离子铑配合物如[Rh（cod）2] BF4和PPh3的存在下获得取代的喹啉衍生物。乙苯是这种新的氧化反应中的副产物。苯乙烯与苯胺的第一过渡金属催化的反马氏化学加氢胺化反应为副反应。机理研究强烈支持苯乙烯的区域选择性氧化胺化作为关键反应步骤。
• Ytterbium(III) triflate catalyzed domino reaction of arylamines and styrene oxides: Synthesis of 2-benzyl-3-arylquinoline derivatives
  作者：Saghir Ali、Abu Taleb Khan

  DOI：10.1016/j.tetlet.2021.152981

  日期：2021.4

  efficient and straightforward method for the synthesis of 2-benzyl-3-arylquinoline derivatives is reported involving the domino reaction of substituted arylamines and styrene oxides in the presence of 10 mol% ytterbium(III) triflate in acetonitrile at 80 °C. Additionally, the reaction of aliphatic epoxides with p-anisidine provided 2,3-dialkylquinoline derivatives under identical reaction conditions. Important

  报道了一种合成 2-苄基-3-芳基喹啉衍生物的高效而直接的方法，该方法涉及取代芳胺和苯乙烯氧化物在 80 °C 下在 10 mol% 镱 （III） 三氟甲磺酸乙腈溶液存在下发生的多米诺反应。 此外，脂肪族环氧化物与 p-茴香胺的反应在相同的反应条件下提供了 2,3-二烷基喹啉衍生物。该方案的重要特点是易于处理、底物范围广、产率高以及形成两个 CN 键和两个 CC 键。
• Sc(OTf)₃-Mediated One-Pot Synthesis of 2,3-Disubstituted Quinolines from Anilines and Epoxides
  作者：Md Shafaat Al Mehedi、Jetze J. Tepe

  DOI：10.1021/acs.joc.0c00803

  日期：2020.5.15

  Here, we report the first synthesis of 2,3-disubstituted quinolines from anilines and aromatic or aliphatic epoxides. This reaction utilizes Sc(OTf)3 as a Lewis acid and TEMPO as an oxygen scavenger. A wide variety of highly substituted quinolines were obtained with moderate to excellent yields (up to 96%).

  在这里，我们报道了由苯胺和芳香族或脂肪族环氧化物首次合成2,3-二取代喹啉。该反应利用Sc（OTf）3作为路易斯酸和使用TEMPO作为除氧剂。以中等至极好的收率（高达96％）获得了各种高度取代的喹啉。
• Metal-Free, Ionic Liquid-Mediated Synthesis of Functionalized Quinolines
  作者：Jaideep B. Bharate、Sandip B. Bharate、Ram A. Vishwakarma

  DOI：10.1021/co500047w

  日期：2014.11.10

  An expedient and metal-free synthetic protocol for construction of substituted quinolines has been developed from anilines and phenylacetaldehydes using imidazolium cation-based ionic liquids as the reaction medium. Mechanistic analysis indicated that the reaction occurs through C-C and C-N bond formation to produce isolable 2,3-disubstituted quinoline intermediates, which undergo C-C bond cleavage to produce 3-substituted quinolines. The reaction proceeds smoothly with a range of functionalities in good to excellent yields. Advantages of this protocol include metal-free, environmentally friendly, recyclable reaction media, higher yields and shorter reaction times, and thus is promising for the efficient combinatorial synthesis of structurally diverse 2,3-disubstituted and 3-substituted quinolines.
• Efficient One-Pot Synthesis of 2-Alkylquinolines under Solvent-Free Conditions Using Sulfonic Acid Functionalized Ionic Liquid as a Recoverable and Reusable Catalyst
  作者：Min Zhang、Yuqiang Ding、Biao Xiong、Ting Wang、Li Wang

  DOI：10.3987/com-11-12289

  日期：——

  Sulfonic acid functionalized ionic liquid (FIL-A) was firstly used as a recoverable and reusable catalyst for the synthesis of 2-alkylquinoline derivatives from simple and readily available alkylaldehydes and arylamines. The method has the advantages of simple experimental procedure, easy recovery and reuse of catalyst, solvent-free and mild reaction conditions, excellent functional group tolerance, etc. which makes it a highly practical and environmentally benign pathway for the synthesis of 2-alkylquinolines.