cis-4-(4-hydroxy-3-methoxy-phenyl)-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-hydroxy-3-methoxy-phenyl)-3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-methoxy-4-[(2R,3R,4S)-3-methyl-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl]phenol
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: IWAXDKIPUBCHLU-AIYSXCBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 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：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 、 苯甲醛 、 苯胺 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 生成 cis-4-(4-hydroxy-3-methoxy-phenyl)-3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  4-Hydroxy-3-methoxyphenyl Substituted 3-methyl-tetrahydroquinoline Derivatives Obtained Through Imino Diels-Alder Reactions as Potential Antitumoral Agents

  摘要：

  研究人员首次测试了两个系列的 17 种四氢喹啉化合物（2,4-DAr-THQs 和 DSQs）对 MCF-7、SKBR-3、PC3、HeLa 以及非肿瘤细胞（人真皮成纤维细胞原代培养--对照细胞）的潜在人类肿瘤细胞生长抑制作用。THQ 8 是一种有趣的抗肿瘤药物模型，对 MCF7、SKBR3 或 PC3 具有细胞毒性活性（IC50 为 7.99 - 16.14 μM），对 MCF7 的选择性指数为 3.4。

  DOI：

  10.2174/157018010792929577

文献信息

• 4-Hydroxy-3-methoxyphenyl Substituted 3-methyl-tetrahydroquinoline Derivatives Obtained Through Imino Diels-Alder Reactions as Potential Antitumoral Agents
  作者：Vladimir V. Kouznetsov、Diego R. Merchan Arenas、Francisco Arvelo、Josue S. Bello Forero、Felipe Sojo、Arturo Munoz

  DOI：10.2174/157018010792929577

  日期：2010.11.1

  Two series of 17 tetrahydroquinoline compounds (2,4-DAr-THQs and DSQs), in which the 4-methoxy-3- hydroxyphenyl (isovanillin) structural unit is incorporated, were tested for their potential human tumor cell growth inhibitory effect on MCF-7, SKBR-3, PC3, HeLa and for non-tumor cells (primary culture of human dermis fibroblast – control cells) for the first time. The THQ 8 is an interesting model for antitumoral drugs, displaying cytotoxic activity against MCF7, SKBR3 or PC3 (IC50 7.99 - 16.14 μM) with the selectivity index 3.4 for MCF7.

  研究人员首次测试了两个系列的 17 种四氢喹啉化合物（2,4-DAr-THQs 和 DSQs）对 MCF-7、SKBR-3、PC3、HeLa 以及非肿瘤细胞（人真皮成纤维细胞原代培养--对照细胞）的潜在人类肿瘤细胞生长抑制作用。THQ 8 是一种有趣的抗肿瘤药物模型，对 MCF7、SKBR3 或 PC3 具有细胞毒性活性（IC50 为 7.99 - 16.14 μM），对 MCF7 的选择性指数为 3.4。
• 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.
• 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。