ethyl 4-(3-methylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 1426332-74-2

• 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-(3-methylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 2,7,7-trimethyl-5-oxo-4-(m-tolyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 2,7,7-trimethyl-4-(3-methylphenyl)-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 1426332-74-2
• 化学式: C₂₂H₂₇NO₃
• 分子量: 353.461
• InChiKey: PPNWCMIAXAGWAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 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 、 3-甲基苯甲醛 在 ammonium acetate 、 chitosan 作用下， 反应 0.13h， 以88%的产率得到ethyl 4-(3-methylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  壳聚糖：一种在无溶剂条件下绿色合成1,4-二氢吡啶衍生物的可持续，可重复使用和可生物降解的有机催化剂

  摘要：

  摘要 壳聚糖是一种可生物降解的绿色催化剂，被发现是一种令人印象深刻的系统，可用于不同醛，二甲酮，β-酮酸酯或乙酰乙酰苯胺和乙酸铵的单锅四组分反应，通过汉茨型缩合反应生成1,4-二氢吡啶衍生物在无溶剂条件下。这种方法具有多种优势，例如操作简便，反应时间短，满意的产率和可回收的催化剂。在这项工作中，我们尝试对经典的Hantzsch转换进行一些修改，以报告一种新颖的环保方法，该方法没有以前报道的缺点。 图形概要

  DOI：

  10.1007/s11164-016-2579-7

文献信息

• 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。
• Cd(NO₃)₂.4H₂O Catalyzed One-Pot Synthesis of 1,4-Dihydropyridine and Polyhydroquinoline Derivatives through the Hantzsch Multicomponent Condensation
  作者：Radia Tafer、Raouf Boulcina、Bertrand Carboni、Abdelmadjid Debache

  DOI：10.1002/jccs.201200162

  日期：2012.12

  The synthesis of various 1,4‐dihydropyridine and polyhydroquinoline derivatives was achieved in good to excellent yields using cadmium (II) nitrate as catalyst to promote the classical and modified Hantzsch conditions in good yields under mild conditions.

  使用硝酸镉（II）作为催化剂，以温和的条件下以良好的收率促进经典和改良的Hantzsch条件，合成了各种1,4-二氢吡啶和聚氢喹啉衍生物，收率良好至优异。
• An Efficient, One-Pot Synthesis of Polyfunctionalised Dihydropyridines Catalysed by AgI Nanoparticles
  作者：Mohammad Ali Ghasemzadeh、Javad Safaei-Ghomi

  DOI：10.3184/174751914x13976454726953

  日期：2014.5

  Polyfunctionalised dihydropyridines were synthesised in high yields and in short reaction times by a four-component reaction of araldehydes, dimedone, ethyl acetoacetate and ammonium acetate in the presence of AgI nanoparticles in aqueous ethanol media under reflux conditions. The catalyst was easily prepared and was recyclable.

  在回流条件下，AgI 纳米粒子在乙醇水介质中存在的情况下，通过芳醛、二甲基酮、乙酰乙酸乙酯和乙酸铵的四组分反应，高产率、短反应时间地合成了多官能度的二氢吡啶类化合物。该催化剂易于制备且可回收利用。
• Sulfonamide-functionalized covalent organic framework (COF-SO3H): an efficient heterogeneous acidic catalyst for the one-pot preparation of polyhydroquinoline and 1,4-dihydropyridine derivatives
  作者：Razieh Farsi、Mohammad Kazem Mohammadi、Seyyed Jafar Saghanezhad

  DOI：10.1007/s11164-020-04322-5

  日期：2021.3

  as an acidic porous catalyst for the one-pot preparation of polyhydroquinoline and 1,4-dihydropyridine derivatives. COF-SO3H was characterized by FT-IR, EDX, TGA, SEM, XRD, and BET. This methodology offers several advantages including high yield, short reaction time, simple workup procedure, solvent-free conditions, ease of separation, and recyclability. Graphic abstract One-pot preparation of polyhydroquinoline

  本文中，我们报道了由三聚氰胺和对苯二甲醛和随后的磺化反应制备的磺酰胺官能化共价有机骨架（COF-SO 3 H），该酸性骨架催化剂是一锅制备聚氢喹啉和1,4-二氢吡啶衍生物的酸性多孔催化剂。通过FT-IR，EDX，TGA，SEM，XRD和BET对COF-SO 3 H进行了表征。该方法具有许多优点，包括高收率，较短的反应时间，简单的后处理程序，无溶剂条件，易于分离和可回收性。 图形摘要 一锅法制备多氢喹啉和1,4-二氢吡啶衍生物
• Choline Chloride Catalyzed Eco-Friend and Effective One-Pot Synthesis of 9-Arylacridine-1,8-dione and Hexahydroquinoline via Hantzsch Type Reaction
  作者：Chengwei Lv、Shijun Yu、Shengxue Mao、Fei Li、Yue Lv

  DOI：10.3987/com-17-13760

  日期：——

  Choline chloride was utilized to efficiently catalyzed Hantzsch type reaction for the synthesis of 9-arylacridine-1,8-dione and hexahydroquinoline derivatives. The optimized catalytic system benefits from facile operation and separation procedures, in good to excellent yields, and for wide substrate tolerance. This methodology is of interest also due to employing simple and inexpensive choline chloride as catalyst and environmentally benign ethanol as solvent without the use of any harmful organic solvent and toxic metal catalyst.