methyl 4‐(4‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐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: methyl 4‐(4‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate
• 英文别名: methyl 4-(4-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylate；methyl 4-(4-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；methyl 4-(4-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₀H₂₂ClNO₃
• 分子量: 359.853
• InChiKey: GTKHYYJGYAEFIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3-羟基-5,5-二甲基环己-2-烯-1-酮 、 4-氯苯甲醛 、 乙酰乙酸甲酯 在 C₅₂H₄₆Cr₃FN₄O₂₅ 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到methyl 4‐(4‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate
  参考文献：
  名称：

  在开放金属位点Cr-MOF上进行乙二胺的合成后修饰，以得到用于Hantzsch缩合反应的高效双功能催化剂

  摘要：

  乙二胺官能化的MIL-101（Cr）被确立为通过在水性介质中醛，二甲酮，β-酮缩酮和乙酸铵之间的四组分缩合反应来单锅合成多氢喹啉的有效有机催化剂。母体开放金属位点MIL-101（Cr）的乙二胺已通过合成后修饰（PSM）技术进行了研究。高效的转化，温和的条件，容易的产物分离以及有机催化剂的潜在高回收率是该协议的关键特征。

  DOI：

  10.1002/aoc.4370

文献信息

• 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。
• 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。
• Zn/MCM-41-catalyzed unsymmetrical Hantzsch reaction and the evaluation of optical properties and anti-cancer activities of the polyhydroquinoline products
  作者：Elaheh Farajzadeh Oskuie、Sajjad Azizi、Zarrin Ghasemi、Mahtab Pirouzmand、Behnaz Nikzad Kojanag、Jafar Soleymani

  DOI：10.1007/s00706-020-02549-x

  日期：2020.2

  investigated in the presence of MCM-41-supported ZnNO3. The polyhydroquinoline products which were obtained under mild conditions and very easy workup were evaluated for anti-cancer activities against MCF-7, SK-BR-3, and HT-29 of breast and colon cancer cells. The fluorescence emission of some products was also studied and their optical parameters were reported. Graphic abstract

  摘要在MCM-41负载的ZnNO 3的存在下，研究了各种芳基醛，二甲酮和3-氨基巴豆酸甲酯的三组分Hantzsch缩合反应。评价了在温和条件下和很容易处理后获得的聚氢喹啉产品对乳腺癌和结肠癌细胞的MCF-7，SK-BR-3和HT-29的抗癌活性。还研究了一些产物的荧光发射，并报道了它们的光学参数。 图形摘要
• Mo@GAA-Fe₃O₄ MNPs: a highly efficient and environmentally friendly heterogeneous magnetic nanocatalyst for the synthesis of polyhydroquinoline derivatives
  作者：Mehraneh Aghaei-Hashjin、Asieh Yahyazadeh、Esmayeel Abbaspour-Gilandeh

  DOI：10.1039/d1ra00396h

  日期：——

  Polyhydroquinolines were obtained from a sequential four-component reaction between dimedone or 1,3-cyclohexandione, ethyl acetoacetate, or methyl acetoacetate as a β-ketoester, aldehydes, and ammonium acetate, with Mo@GAA-Fe3O₄ MNPs as a green nanocatalyst.

  聚羟基喹啉是通过二甲二酮或1,3-环己二酮、乙酰乙酸乙酯或乙酰乙酸甲酯作为β-酮酯、醛和醋酸铵的顺序四组分反应获得的，使用Mo@GAA-Fe3O4磁性纳米颗粒作为绿色纳米催化剂。
• Periodic mesoporous organosilica with ionic-liquid framework supported manganese: an efficient and recyclable nanocatalyst for the unsymmetric Hantzsch reaction
  作者：M. Nasr-Esfahani、D. Elhamifar、T. Amadeh、B. Karimi

  DOI：10.1039/c4ra12673d

  日期：——

  unsymmetric Hantzsch reaction using an ionic liquid based periodic mesoporous organosilica supported manganese (Mn@PMO-IL) catalyst under solvent-free conditions is described. This catalyst showed high reactivity and selectivity for the preparation of a set of different derivatives of polyhydroquinolines under moderate reaction conditions and short times. Moreover, the catalyst was also recovered and reused

  生物活性取代polyhydroquinoline衍生物的绿色和快速合成的有效方法通过描述了在无溶剂条件下使用基于离子液体的周期性介孔有机二氧化硅负载的锰（Mn @ PMO-IL）催化剂进行的不对称Hantzsch反应。该催化剂在中等反应条件和短时间内制备一组不同的聚氢喹啉衍生物具有很高的反应活性和选择性。此外，在不显着降低反应性和产率的情况下，催化剂也被回收并重复使用了几次。回收的催化剂的氮吸附-解吸和透射电子显微镜显着证明了在所应用的反应条件下催化剂的高稳定性和耐久性。此外，与传统方法相比，该方法始终显示出反应时间短，催化剂用量低，收率高，