cis-4-(4-methoxyphenyl)-3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline

• 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: cis-4-(4-methoxyphenyl)-3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (2R,3R,4S)-4-(4-methoxyphenyl)-3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: WDMFRCAMGZSKPP-UZFJHSOTSA-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：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 、 苯胺 、 茴香烯 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 10.5h， 以52%的产率得到cis-4-(4-methoxyphenyl)-3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  In Vitro Activity Against Trypanosoma cruzi and Leishmania chagasi Parasites of 2,4-Diaryl 1,2,3,4-Tetrahydroquinoline Derivatives

  摘要：

  采用三氟化硼二乙醚合物催化的三组分席夫碱Diels-Alder反应可轻松制备功能多样化的四氢喹啉，并对其实验室体外抗克氏锥虫和查加斯利什曼原虫寄生虫活性以及使用非洲绿猴肾细胞（Vero细胞）和人类单核细胞白血病细胞（THP-1细胞）的细胞毒性进行了测试。这些研究表明，活性最高的化合物是7h，其对克氏锥虫的IC50值为5.77±0.21 μM，IC90值为40.43±1.58 μM；对查加斯利什曼原虫的IC50值为0.27±0.03 μM，IC90值为2.16±0.37 μM。与参考药物相比，其选择性指数（SI）值更高（在克氏锥虫的利氏曼型和查加斯利什曼原虫的动虫型中分别SI为46和SI为1000）。此外，化合物7h对Vero细胞或THP-1细胞无细胞毒性（IC50>270 μM）。

  DOI：

  10.2174/157018012802652994

文献信息

• Cu(OTf)2-Catalyzed Three-Component Imino Diels-Alder Reaction Using Propenylbenzenes: Synthesis of 2,4-Diaryl Tetrahydroquinoline Derivatives
  作者：Arnold R. Romero Bohorquez、Vladimir V. Kouznetsov、Michael P. Doyle

  DOI：10.2174/157017811794557831

  日期：2011.1.1

  Copper(II) triflate mediated three-component [4+2]-cycloaddition reactions between anilines, benzaldehydes and trans-anethole or trans-isoeugenol are reported. A simple and efficient one-pot method for the synthesis of diverse 2,4-diaryl-1,2,3,4-tetrahydroquinolines under mild conditions in the presence of catalytic amounts (10 mol %) of Cu(OTf)2 was developed. Attempts toward an asymmetric imino Diels-Alder reaction are discussed.

  报道了铜(II)三氟甲磺酸盐介导的三组分[4+2]环加成反应，涉及苯胺、苯甲醛与反式茴香脑或反式异丁子香油的反应。开发了一种简便高效的一锅法，在温和条件下，仅需催化量（10 mol%）的Cu(OTf)2，即可合成多种2,4-二芳基-1,2,3,4-四氢喹啉。同时讨论了不对称亚胺Diels-Alder反应的尝试。
• Experimental and Theoretical Studies on the Radical-Cation-Mediated Imino-Diels–Alder Reaction
  作者：Raul Pérez-Ruiz、Luis R. Domingo、M. Consuelo Jiménez、Miguel A. Miranda

  DOI：10.1021/ol201984s

  日期：2011.10.7

  The feasibility of an electron transfer imino-Diels–Alder reaction between N-benzylideneaniline and arylalkenes in the presence of a pyrylium salt as a photosensitizer has been demonstrated by a combination of product studies, laser flash photolysis (LFP), and DFT theoretical calculations. A stepwise mechanism involving two intermediates and two transition states is proposed.

  结合产品研究，激光闪光光解（LFP）和DFT理论计算，证明了在吡喃鎓盐存在下N-苄叉基苯胺和芳基烯烃之间进行电子转移亚氨基Diels-Alder反应的可行性。提出了一种涉及两个中间体和两个过渡态的逐步机理。
• Three-component imino Diels–Alder reaction with essential oil and seeds of anise: generation of new tetrahydroquinolines
  作者：Vladimir V. Kouznetsov、Arnold R. Romero Bohórquez、Elena E. Stashenko

  DOI：10.1016/j.tetlet.2007.10.063

  日期：2007.12

  A simple and efficient one-pot method for the synthesis of 4-anisyl-2-phenyl-1,2,3,4-tetrahydroquinoline derivatives using a three-component imino Diels–Alder cycloaddition (Povarov reaction) between anilines, benzaldehyde, and trans-anethole in the presence of acidic catalysts is shown. New substituted tetrahydroquinolines are reported and their direct preparation from the anise essential oil is described

  一种简单高效的一锅法，可使用苯胺，苯甲醛和苯胺之间的三组分亚氨基Diels-Alder环加成反应（Povarov反应）合成4-茴香基-2-苯基-1，2，3，4-四氢喹啉衍生物。显示了在酸性催化剂存在下的反式茴香脑。报道了新的取代的四氢喹啉，并描述了它们从茴香精油中的直接制备。另外，已经报道了在超临界流体（CO 2）条件下从茴香种子中提取相同的四氢喹啉的简单方法。
• Pyrylenes: A New Class of Tunable, Redox-Switchable, Photoexcitable Pyrylium–Carbene Hybrids with Three Stable Redox-States
  作者：Patrick W. Antoni、Max M. Hansmann

  DOI：10.1021/jacs.8b08545

  日期：2018.11.7

  molecules based upon the combination of pyrylium salts and carbenes is presented. The redox-properties of this new molecule class correlate very well with the π-accepting properties of the corresponding carbenes. While the pyrylium moiety acts as a chromophore, the carbene moiety can tune the redox-properties and stabilize the corresponding radicals. This leads to the isolation of the first monomeric pyranyl-radical

  提出了一种新的合成和模块化方法，可以访问基于pyrylium 盐和卡宾的一大类氧化还原可转换分子。这种新分子类别的氧化还原特性与相应卡宾的 π 接受特性非常相关。虽然pyrylium 部分充当发色团，但卡宾部分可以调整氧化还原性能并稳定相应的自由基。这导致固态中第一个单体吡喃基的分离。三种稳定的氧化态可以通过化学氧化干净地获得，由 NMR、EPR、UV-vis 和 X 射线衍射表征并得到 (TD)-DFT 计算的支持。新的混合类可用作电化学触发开关和强大的光激发还原剂。重要的，
• PEG-400 as green reaction medium for Lewis acid-promoted cycloaddition reactions with isoeugenol and anethole
  作者：Vladimir V. Kouznetsov、Diego R. Merchan Arenas、Arnold R. Romero Bohórquez

  DOI：10.1016/j.tetlet.2008.03.049

  日期：2008.5

  A simple and efficient one-pot method for the synthesis of new 2,4-diaryl-1,2,3,4-tetrahydroquinolines using a three-component imino Diels-Alder cycloaddition between trans-isoeugenol or trans-anethole, anilines, and benzaldehyde in the presence of BF3 center dot OEt2 in PEG-400, a green and reusable solvent, has been developed. Also, BF3 center dot OEt2-catalyzed formal [3+2] cycloaddition reaction of tralls-isoeugenol or trans-anethole with 1,4-benzoquinone in PEG-400 to give dihydrobenzo[b]furan derivatives has been described. (C) 2008 Elsevier Ltd. All rights reserved.