ethyl 2,7,7-trimethyl-5-oxo-4-(4-hydroxylphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

• 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 2,7,7-trimethyl-5-oxo-4-(4-hydroxylphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；2,7,7-trimethyl-5-oxo-4-(4-hydroxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester；ethyl 2,7,7-trimethyl-5-oxo-4-(4-hydroxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: GFDTWMMIHOBFFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2,7,7-trimethyl-5-oxo-4-(4-hydroxylphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以90%的产率得到ethyl 2,7,7-trimethyl-5-oxo-4-(4-(prop-2-ynyloxy)phenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Fluorescent supramolecular tweezers for selective recognition of cephradine

  摘要：

  Novel supramolecular molecular tweezers based on a biphenyl bis-triazole hexahydroquinoline system are designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting cephradine in the presence of cefotaxime, amoxicillin, penicillin, 6-.aminopenicillanic acid, diclofenac, pefloxacin, ceftriaxone, cefaclor and paracetamol at a pH of 7.7. The detection limit is calculated to be 1 mu M with a regression coefficient of 0.99. The binding ratio of the tweezers and cephradine is determined to be 1:1 according to ESI-MS analysis, which is further supported by the Job plot. The structure of the supramolecular molecular tweezers and its precursors are characterized by IR, NMR, mass spectroscopy and XRD. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.040
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2,2′‐[(4‐hydroxyphenyl)methylene]bis(3‐hydroxy‐5,5‐dimethylcyclohex‐2‐enone) 在 乙酸铵 、 baker's yeast 、 葡萄糖 作用下， 以 phosphate buffer 为溶剂， 反应 24.0h， 生成 ethyl 2,7,7-trimethyl-5-oxo-4-(4-hydroxylphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Bakers’ yeast catalyzed synthesis of polyhydroquinoline derivatives via an unsymmetrical Hantzsch reaction

  摘要：

  Bakers' yeast efficiently catalyzes the unsymmetrical Hantzsch reaction through a four-component coupling of aldehydes, beta-ketoesters, dimedone and ammonium acetate to form polyhydroquinoline derivatives in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.130

文献信息

• Heterogeneous Cu(<scp>ii</scp>)/<scp>l</scp>-His@Fe₃O₄ nanocatalyst: a novel, efficient and magnetically-recoverable catalyst for organic transformations in green solvents
  作者：Masoomeh Norouzi、Arash Ghorbani-Choghamarani、Mohsen Nikoorazm

  DOI：10.1039/c6ra19776k

  日期：——

  A novel, efficient and green Cu(II)/L-His@Fe3O4 catalyst has been applied successfully in the synthesis of heterocyclic compounds. The resulting catalyst was used in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, polyhydroquinolines and 2-amino-6-(arylthio)pyridine-3,5-dicarbonitriles as biologically interesting compounds. The present research is focused on investigation of recycling, reusability

  一种新颖，高效，绿色的Cu（II）/ L- His @ Fe 3 O 4催化剂已成功用于杂环化合物的合成。所得催化剂用于合成2，3-二氢喹唑啉-4（1H）-酮，聚氢喹啉和2-氨基-6-（芳硫基）吡啶-3，5-二碳腈作为生物学上感兴趣的化合物。本研究的重点是研究相反应中催化剂的循环利用，可重复使用性和稳定性。Cu（II）/ L -His @ Fe 3 O 4该催化剂至少使用了六次，其活性与新鲜催化剂相当。通过TGA / DTG，EDS，XRD，VSM，FT-IR和SEM对催化剂的化学组成和结构进行了分析。
• Cu-<i>S</i>-(propyl)-2-aminobenzothioate on magnetic nanoparticles: highly efficient and reusable catalyst for synthesis of polyhydroquinoline derivatives and oxidation of sulfides
  作者：Arash Ghorbani-Choghamarani、Bahman Tahmasbi、Parisa Moradi、Nasrin Havasi

  DOI：10.1002/aoc.3478

  日期：2016.8

  Cu–S‐(propyl)‐2‐aminobenzothioate supported on functionalized Fe3O4 magnetic nanoparticles is reported as a reusable and highly efficient nanocatalyst for the one‐pot synthesis of polyhydroquinoline derivatives and also for selective oxidation of sulfides to sulfoxides. The prepared nanoparticles were characterized using Fourier transform infrared spectroscopy, vibrating sample magnetometry, thermogravimetric

  官能化的Fe 3 O 4上负载的Cu- S-（丙基）-2-氨基苯甲硫醇据报道，磁性纳米颗粒是一种可重复使用的高效纳米催化剂，可用于单锅合成多氢喹啉衍生物，也可用于将硫化物选择性氧化为亚砜。使用傅里叶变换红外光谱仪，振动样品磁力分析，热重分析，透射和扫描电子显微镜，能量色散X射线光谱，X射线衍射，电感耦合等离子体原子发射光谱和原子吸收光谱对制备的纳米颗粒进行表征。使用外部磁体可以容易地回收纳米催化剂，并且可以在不显着损失其催化效率的情况下重复使用几次。版权所有©2016 John Wiley＆Sons，Ltd.
• Synthesis and characterization of spinel FeAl2O4 (hercynite) magnetic nanoparticles and their application in multicomponent reactions
  作者：Arash Ghorbani-Choghamarani、Masoud Mohammadi、Lotfi Shiri、Zahra Taherinia

  DOI：10.1007/s11164-019-03930-0

  日期：2019.11

  The spinel ferrite FeAl2O4 (hercynite) MNPs (magnetic nanoparticles) were applied as a reusable catalytic system for the one-pot synthesis of benzo[ a ]pyrano[2,3-c] phenazine and polyhydroquinoline derivatives via a multicomponent reaction under green reaction conditions. The structure of the prepared nanocatalyst has been characterized by XRD, FTIR, SEM, EDS, BET, and VSM techniques. The FeAl2O4

  尖晶石型铁氧体FeAl 2 O 4（水铁矿）MNP（磁性纳米粒子）被用作可重复使用的催化体系，用于在以下条件下通过多组分反应一锅合成苯并[ a ]吡喃并[2,3-c]吩嗪和聚氢喹啉衍生物。绿色反应条件。制备的纳米催化剂的结构已通过XRD，FTIR，SEM，EDS，BET和VSM技术进行了表征。FeAl 2 O 4 MNP起到路易斯酸的作用，并具有许多优点，例如产物的收率高，反应时间短和后处理程序容易。此外，再循环的纳米催化剂被使用了至少四次而其活性没有明显损失。
• Introduction of an efficient DABCO-based bis-dicationic ionic salt catalyst for the synthesis of arylidenemalononitrile, pyran and polyhydroquinoline derivatives
  作者：Mehdi Zabihzadeh、Atefeh Omidi、Farhad Shirini、Hassan Tajik、Mohaddeseh Safarpoor Nikoo Langarudi

  DOI：10.1016/j.molstruc.2020.127730

  日期：2020.4

  Abstract —An affordable DABCO-based bis-dicationic ionic salt ([(DABCO)2C3H5OH]·2Cl) was utilized for the synthesis of arylidenemalononitrile, tetrahydrobenzo[b]pyran, pyrano[2,3-d]-pyrimidinone (thione), dihydropyrano[3,2-c]chromene, and polyhydroquinoline derivatives. The significant features of the presented method are ease of preparation and handling of the catalyst, high catalytic activity, short

  摘要 —一种经济实惠的基于 DABCO 的双阳离子离子盐 ([(DABCO)2C3H5OH]·2Cl) 用于合成亚芳基丙二腈、四氢苯并[b]吡喃、吡喃并[2,3-d]-嘧啶酮（硫酮），二氢吡喃并[3,2-c]色烯和聚氢喹啉衍生物。该方法的显着特点是催化剂易于制备和处理，催化活性高，反应时间短，无需柱色谱分离，后处理程序简单。此外，催化剂可以很容易地回收并在研究的反应中重复使用几个循环。
• 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。