methyl 2,7,7-trimethyl-5-oxo-4-p-tolyl-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: methyl 2,7,7-trimethyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: 2,7,7-trimethyl-5-oxo-4-(4-methylphenyl)-1,4,5,6,7,8,-hexahydroquinoline-3-carboxylic acid methyl ester；2,7,7-trimethyl-5-oxo-4-(4-methylphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester；2,7,7-trimethyl-5-oxo-4-tolyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester；methyl 2,7,7-trimethyl-5-oxo-4-(p-tolyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；Methyl 2,7,7-trimethyl-4-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；methyl 2,7,7-trimethyl-4-(4-methylphenyl)-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₁H₂₅NO₃
• 分子量: 339.434
• InChiKey: SHSSGEPOJXCVPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  对甲基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 乙酰乙酸甲酯 在 sulfamic acid-functionalized _Fe3-xTi_xO₄ magnetic nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以94%的产率得到methyl 2,7,7-trimethyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Fe 3-x Ti x O 4负载的氨基磺酸纳米颗粒：用于合成六氢喹啉的新型磁性纳米催化剂

  摘要：

  一种新的酸性纳米催化系统，氨基磺酸官能化的Fe 3-x的Ti X Ò 4的磁性纳米颗粒（的MNP），是通过铁的一锅反应合成的3-X的Ti X Ò 4用3-氯丙基三甲氧基硅烷和咪唑烷-2,4-二酮的MNP，然后用氯磺酸官能化。通过几种分析方法建立了这种新合成的纳米催化剂的结构，包括傅立叶变换红外（FTIR）和能量分散X射线（EDX）光谱，透射（TEM）和扫描（SEM）电子显微镜，热重（TG） ），X射线衍射（XRD）和振动样品磁力计（VSM）。为了合成六氢喹啉衍生物，在芳族醛，二甲酮，乙酰乙酸烷基酯和乙酸铵之间的一锅四组分缩合反应中评估了该纳米催化剂的潜在催化能力。该反应在无溶剂条件下顺利进行，成功地提供了极佳的相应六氢喹啉收率。

  DOI：

  10.1016/j.jorganchem.2019.05.020

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。
• 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。
• One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives in fluoro alcohols
  作者：Akbar Heydari、Samad Khaksar、Mahmood Tajbakhsh、Hamid Reza Bijanzadeh

  DOI：10.1016/j.jfluchem.2009.03.014

  日期：2009.7

  Hantzsch 1,4-dihydropyridine, polyhydroquinoline and 1,8-dioxodecahydroacridines derivatives were synthesized in excellent yields in trifluoroethanol (TFE). The solvent (TFE) can be readily separated from reaction products and recovered in excellent purity for direct reuse.

  在三氟乙醇（TFE）中以极高的收率合成了Hantzsch 1,4-二氢吡啶，聚氢喹啉和1,8-二氧杂十二烷基hydro啶衍生物。溶剂（TFE）可以很容易地从反应产物中分离出来，并以极高的纯度回收以直接使用。
• 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，