2,7,7-trimethyl-5-oxo-4-(2-methoxyphenyl)-1,4,5,6,7,8,-hexahydroquinoline-3-carboxylic acid ethyl ester

• 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: 2,7,7-trimethyl-5-oxo-4-(2-methoxyphenyl)-1,4,5,6,7,8,-hexahydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2,7,7-trimethyl-5-oxo-4-(2-methoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 4-(2-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；2,7,7-trimethyl-4-(2-methoxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester；ethyl 4-(2-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: PVCGMZDEZYIOOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2,2'-(2-methoxyphenyl)methylene-bis-(3-hydroxy-5, 5-dimethyl-2-cyclohexene-1-one) 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 2,7,7-trimethyl-5-oxo-4-(2-methoxyphenyl)-1,4,5,6,7,8,-hexahydroquinoline-3-carboxylic acid ethyl ester
  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

• Poly(vinylpyrrolidinium) perchlorate as a new and efficient catalyst for the promotion of the synthesis of polyhydroquinoline derivatives via Hantzsch condensation
  作者：Masoumeh Abedini、Farhad Shirini、Maryam Mousapour

  DOI：10.1007/s11164-015-2150-y

  日期：2016.3

  poly(vinylpyrrolidinium) perchlorate [PVPH]ClO4} as a new modified polymeric catalyst in the absence of solvent is reported. The title catalyst is easily prepared and characterized using a variety of techniques including infrared spectra, X-ray diffraction, thermal gravimetric analysis, scanning electron microscopy, pH analysis, and Hammett acidity function. Some of the advantages of this novel synthetic method are:

  报道了一种在没有溶剂的情况下使用聚（乙烯基吡咯烷鎓）高氯酸盐[PVPH] ClO 4 }作为新型改性聚合物催化剂来促进汉茨产物合成的绿色方法。标题催化剂易于使用多种技术制备和表征，包括红外光谱，X射线衍射，热重分析，扫描电子显微镜，pH分析和哈米特酸度函数。这种新颖的合成方法的一些优点是：催化剂易于制备，反应时间短，产物的产率高至优异，后处理步骤简单容易以及催化剂的可重复使用性。
• Preparation and characterization of Cu (II) supported on poly(8-hydroxyquinoline-<i>p</i> -styrene sulphonate) and its application as catalyst for the synthesis of hexahydroquinolines
  作者：Ardeshir Khazaei、Mahsa Tavasoli、Vahid Jamshidi、Fatemeh Gohari Ghalil、Ahmad Reza Moosavi-Zare

  DOI：10.1002/aoc.4368

  日期：2018.7

  Cu (II) supported on poly(8‐hydroxyquinoline‐p‐styrenesulfonate) (Cu (II)@PHQSS) was prepared and fully characterized by the different techniques including fourier transform infrared spectroscopy (FT‐IR), 1H NMR, 13C NMR, thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), differential thermal analysis (DTA), scanning electron microscope (SEM) and energy dispersive X‐ray analysis

  的Cu（II）负载在聚（8- hydroxyquinoline- p -styrenesulfonate）（铜（II）@PHQSS）溶液并充分表征由不同的技术，包括傅里叶变换红外光谱（FT-IR），1 H NMR，13 C ^ NMR，热重分析（TGA），差热重分析（DTG），差热分析（​​DTA），扫描电子显微镜（SEM）和能量色散X射线分析（EDS）。然后，将Cu（II）@PHQSS作为纳米结构催化剂用作合成六氢喹啉的催化剂。
• Synthesis and biological evaluation of new series 1,4-dihydropyridines
  作者：Ramin Ghorbani-Vaghei、Seyedeh Mina Malaekehpoor、Parisa Hasanein、Roya Karamyan、Mostafa Asadbegy

  DOI：10.1007/s11164-015-2310-0

  日期：2016.5

  Abstract N , N , N ′, N ′-Tetrachlorobenzene-1,3-disulfonamide and poly( N , N ′-dichloro- N -ethyl-benzene-1,3-disulfonamide) are new catalysts promoted by one-pot, facile and four-component synthesis of new substituted 1,4-dihydropyridine derivatives from the reaction of ammonium acetate, aldehydes and various 1,3-dicarbonyl compounds with good to high yields at room temperature under mild conditions

  摘要 N ， N ， N '， N'- 四氯苯-1,3-二磺酰胺和聚（ N ， N'- 二氯 -N -乙基-苯-1,3-二磺酰胺）是通过乙酸铵，醛和各种1,3-二羰基的反应通过一锅，简便和四组分合成新的取代的1,4-二氢吡啶衍生物而开发的新型催化剂在室温和温和条件下具有良好到高收率的化合物。评价所有合成的化合物的抗菌和抗氧化活性。确定了对四种革兰氏阳性和阴性细菌的抗菌活性，并通过2,2-二苯基-1-吡啶并肼基自由基清除作用评估了抗氧化活性。生物测定结果表明，合成的1，4-二氢吡啶衍生物具有有效的抗氧化和抗菌作用。 图形摘要 新系列二氢吡啶的合成和生物学评价。
• Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol
  作者：Shi-Jun Yü、Si Wu、Xin-Min Zhao、Cheng-Wei Lü

  DOI：10.1007/s11164-016-2814-2

  日期：2017.5

  A simple, clean, and economical methodology for the synthesis of acridine-1,8-dione and hexahydroquinoline derivatives via Hantzsch-type condensation has been described. This study highlights the development of a new green pathway for the preparation of substituted 1,4-dihydropyridines derivatives. The mild, cheap, and nontoxic potassium dihydrogen phosphate (KH2PO4) is proved to be an efficient catalyst for the above multi-component reaction to get excellent yields. Widely available and mostly benign catalyst, eco-friendly solvent, and easy purification are among the several attractive features.

  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。
• CoFe₂ O₄ @SiO₂ -CPTES-Guanidine-Cu(II): A novel and reusable nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1<i>H</i> )-ones and polyhydroquinolines and oxidation of sulfides
  作者：Leili Heidari、Lotfi Shiri

  DOI：10.1002/aoc.4636

  日期：2019.3

  CoFe2O4@SiO2‐CPTES‐Guanidine‐Cu(II) magnetic nanoparticles were synthesized and used as a new, inexpensive and efficient heterogeneous catalyst for the synthesis of polyhydroquinolines and 2,3‐dihydroquinazoline‐4(1H)‐ones and for the oxidation of sulfides. The structure of this nanocatalyst was characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, energy‐dispersive

  合成了CoFe 2 O 4 @SiO 2 -CPTES-胍基-Cu（II）磁性纳米粒子，并将其用作合成聚氢喹啉和2,3-二氢喹唑啉-4（1 H）的新型，廉价且高效的多相催化剂）-和硫化物的氧化。该纳米催化剂的结构通过傅里叶变换红外光谱，扫描电子显微镜，能量色散X射线光谱，振动样品磁强分析，热重分析，X射线衍射和电感耦合等离子体发射光谱进行了表征。制备简单，催化活性高，操作简单，产率高，使用绿色溶剂，易于磁分离和催化剂的可重复使用性是该方案的一些优点。