ethyl 4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 312527-80-3

• 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: ethyl 4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 312527-80-3
• 化学式: C₂₁H₂₄BrNO₃
• 分子量: 418.33
• InChiKey: WQOLJHTVRJWNHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 5,5-二甲基-1,3-环己二酮 、 邻溴苯甲醛 在 potassium dihydrogenphosphate 、 ammonium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以96%的产率得到ethyl 4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol

  摘要：

  本文描述了一种通过Hantzsch型缩合反应合成吖啶-1,8-二酮和六氢喹啉衍生物的简单、清洁且经济的方法。该研究突出了为制备取代的1,4-二氢吡啶衍生物开发的新型绿色合成途径。温和、廉价且无毒的磷酸二氢钾（KH2PO4）被证明是上述多组分反应的有效催化剂，能够获得优异的产率。广泛可用且基本上无害的催化剂、环保溶剂以及容易的纯化过程是该方法的几个吸引人的特点。

  DOI：

  10.1007/s11164-016-2814-2

文献信息

• TEDETA@BNPs as a basic and metal free nanocatalyst for Knoevenagel condensation and Hantzsch reaction
  作者：Arash Ghorbani-Choghamarani、Zahra Heidarnezhad、Bahman Tahmasbi、Gouhar Azadi

  DOI：10.1007/s13738-018-1417-9

  日期：2018.10

  In this work, Boehmite nanoparticles (BNPs) were synthesized in water using commercially available materials and further N,N,N′,N′-tetraethyldiethylentriamin (TEDETA) was supported on the surface of BNPs, and used as organo-basic catalyst in four-component Hantzsch reaction that provides access to pharmaceutically polyhydroquinoline derivatives and Knoevenagel reaction to afford α,β-unsaturated compounds. All products were obtained in excellent yields (89–98%) and good reaction times under green condition such as water and ethanol solvents. This catalyst was characterized using FT-IR, SEM, EDS, and TGA techniques. This catalyst was reused for several times without the significant loss of their catalytic efficiency. In addition, stability of catalyst after recycling was confirmed by TGA, SEM, EDS and FT-IR techniques.

  在这项工作中，采用商业可得的材料在水中合成了水铝石纳米粒子（BNPs），并进一步在BNPs表面负载了N,N,N′,N′-四乙基二乙烯三胺（TEDETA），用于四组分汉茨施反应中的有机碱催化剂，从而获得制药用的多氢喹啉衍生物，并开展克诺文那尔反应以得到α,β-不饱和化合物。所有产物均在绿色条件下如水和乙醇溶剂中以优异的产率（89-98%）和良好的反应时间获得。该催化剂采用FT-IR、SEM、EDS和TGA技术进行表征。该催化剂在多次重复使用后，其催化效率未显著降低。此外，通过TGA、SEM、EDS和FT-IR技术确认了催化剂再生后仍具有良好的稳定性。
• Praseodymium(<scp>iii</scp>) anchored on CoFe₂O₄ MNPs: an efficient heterogeneous magnetic nanocatalyst for one-pot, multi-component domino synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1<i>H</i>)-one derivatives
  作者：Taiebeh Tamoradi、Seyedeh Masoumeh Mousavi、Masoud Mohammadi

  DOI：10.1039/c9nj05468e

  日期：——

  available materials is reported. The prepared samples were characterized by chemical and physical methods such as FTIR, SEM, XRD and EDX and were tested in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives. It was observed that the yields of the reactions in the presence of the prepared nanocatalyst were good to excellent. More importantly, the use of a recoverable

  在本研究中，报告了一种通过使用可用材料将technique（III）配合物固定在磁性纳米颗粒表面的简便技术。所制备的样品通过化学和物理方法（如FTIR，SEM，XRD和EDX）进行表征，并在合成聚氢喹啉和2,3-二氢喹唑啉-4（1 H）-one衍生物中进行了测试。观察到，在制备的纳米催化剂的存在下，反应的产率良好至优异。更重要的是，在这些反应中使用可回收的新型磁性纳米催化剂是该方案的突出特点。
• PEG-Mediated Catalyst-Free Synthesis of Hantzsch 1,4-Dihydropyridines and Polyhydroquinoline Derivatives
  作者：V. Siddaiah、G. Mahaboob Basha、G. Padma Rao、U. Viplava Prasad、R. Suryachendra Rao

  DOI：10.1080/00397911.2010.528289

  日期：2012.3.1

  Abstract Hantzsch 1,4-dihydropyridines and polyhydroquinoline derivatives were synthesized in good yields by PEG-mediated, catalyst–free synthesis under solvent-free conditions. The products were directly recrystallized from hot methanol. The reaction gave excellent yields with low- as well as high-molecular-weight polyethylene glycols. GRAPHICAL ABSTRACT

  摘要 Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物在无溶剂条件下通过PEG介导的无催化剂合成以良好的收率合成。产物直接从热甲醇中重结晶。该反应对低分子量和高分子量聚乙二醇产生了极好的收率。图形概要
• Melamine supported on hydroxyapatite-encapsulated-γ-Fe2O3: a novel superparamagnetic recyclable basic nanocatalyst for the synthesis of 1,4-dihydropyridines and polyhydroquinolines
  作者：Sedighe Igder、Ali Reza Kiasat、Mohamad Reza Shushizadeh

  DOI：10.1007/s11164-014-1808-1

  日期：2015.10

  γ-Fe2O3@ HAp@Melamine as a magnetic powerful basic nanocatalyst was probed through one-pot synthesis of 1, 4-dihydropyridine and polyhydroquinoline derivatives through Hantzsch condensation reaction under solvent-free thermal conditions. The heterogeneous catalyst could be recovered easily by simple magnetic decantation and reused many times without significant loss of its catalytic activity.

  在本文中，羟基磷灰石包封的γ-Fe的制备和表征2个ö 3纳米颗粒的纳米复合材料三聚氰胺官能（γ-的Fe 2 ö 3 @磷灰石@三聚氰胺）被呈现。通过红外光谱，扫描电子显微镜，热重量分析，X射线衍射，振动样品磁力计和元素分析对所得纳米复合材料进行表征。的催化活性γ-的Fe 2 ö 3通过无溶剂热条件下的Hantzsch缩合反应，通过一锅法合成1，4-二氢吡啶和聚氢喹啉衍生物，探索了HAp @ Melamine作为强磁性的碱性纳米催化剂。通过简单的磁倾析可以很容易地回收非均相催化剂，并且可以多次重复使用而又不会明显丧失其催化活性。
• Efficient one‐pot synthesis of polyhydroquinoline derivatives through the Hantzsch condensation using IRMOF‐3 as heterogeneous and reusable catalyst
  作者：Vaishali N. Rathod、Nilam D. Bansode、Premkumar B. Thombre、Machhindra K. Lande

  DOI：10.1002/jccs.202000303

  日期：2021.4

  surface area analysis (BET). It was applied as an effective heterogeneous catalyst for the synthesis of one‐pot four‐component polyhydroquinoline derivatives via the Hantzsch condensation. The present method offers several advantages over other reported methods such as easy separation, mild reaction condition, and excellent yield of desired product. Furthermore, the catalyst can be reused without loss in

  使用溶剂热法制备了介孔锌基2-氨基对苯二甲酸金属有机骨架（IRMOF-3）催化剂。合成的催化剂通过粉末X射线衍射（XRD），热重分析（TGA），傅里叶变换红外光谱（FT-IR），扫描电子显微镜（SEM），能量分散光谱（EDAX）和Brunauer-Emmett进行表征–柜员表面积分析（BET）。它被用作通过Hantzsch缩合反应合成一锅四组分多氢喹啉衍生物的有效多相催化剂。与其他报道的方法相比，本方法具有一些优点，例如易于分离，温和的反应条件和所需产物的优异收率。此外，催化剂可以重复使用而不会损失活性。