2,7,7-trimethyl-5-oxo-4-(3-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl 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-(3-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester
• 英文别名: 1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(3-nitrophenyl)-5-oxo-chinolin-3-methylat；Methyl 2,7,7-trimethyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；methyl 2,7,7-trimethyl-4-(3-nitrophenyl)-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: PICCUHFXOBODDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 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：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (Z)-2-(3-nitrobenzylidene)-3-oxobutanoate 、 5,5-二甲基-1,3-环己二酮 在 ammonium hydroxide 作用下， 以75%的产率得到2,7,7-trimethyl-5-oxo-4-(3-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Sainani, J. B.; Shah, A. C.; Arya, V. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 6, p. 526 - 531

  摘要：

  DOI：

文献信息

• 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，
• Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines
  作者：Abdolkarim Zare、Fereshteh Abi、Ahmad Reza Moosavi-Zare、Mohammad Hassan Beyzavi、Mohammad Ali Zolfigol

  DOI：10.1016/j.molliq.2012.10.045

  日期：2013.2

  In this work, novel Brønsted acidic ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate [Dsim]HSO4} is synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR, mass, TG, DTG and XRD spectra. This ionic liquid, with three acidic functional groups, is utilized as a highly efficient, homogeneous and reusable catalyst for the preparation of hexahydroquinolines via one-pot multi-component

  在这项工作中，合成了新型的布朗斯台德酸性离子液体1,3-二磺酸咪唑硫酸氢盐[Dsim] HSO 4 }，并通过对其FT-IR，1 H NMR，13 C NMR，质量，TG，DTG进行了表征和XRD光谱。这种具有三个酸性官能团的离子液体被用作高效，均质且可重复使用的催化剂，用于通过一锅多组分芳基醛，二甲酮（5,5-二甲基环己烷-1,3-二酮）的缩合反应制备六氢喹啉），β-​​酮酸酯和乙酸铵在无溶剂条件下使用。催化剂可以使用其SO 3 H基团形成双氢键，该主题可以指导其组装和效率。
• Nano-ferrous ferric oxide (nano-Fe₃O₄): magnetite catalytic system for the one-pot four-component tandem imine/enamine formation-Knoevenagel–Michael-cyclocondensation reaction of dimedone, aldehydes, β-ketoesters and ammonium acetate under green media
  作者：Ardeshir Khazaei、Ahmad Reza Moosavi-Zare、Hadis Afshar-Hezarkhani、Vahid Khakyzadeh

  DOI：10.1039/c4ra03980g

  日期：——

  In this work, magnetite nano-Fe3O4 was applied as a green, efficient, heterogeneous and reusable catalytic system for the atomic economic preparation of hexahydroquinolines via the one-pot multi-component reaction of aryl aldehydes, dimedone (5,5-dimethylcyclohexane-1,3-dione), β-ketoesters and ammonium acetate at 50 °C under mild and solvent-free conditions. The catalyst was synthesized and characterized by several techniques including Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), vibrating sample magnetometry (VSM) and transmission electron microscopy (TEM). Also, optimization of the reaction conditions was investigated using the response surface method Central Composite Design (CCD)}.

  在这项工作中，磁铁矿纳米-Fe3O4被用作一种绿色、高效、异相和可重复利用的催化系统，通过在温和且无溶剂的条件下，在50°C进行芳基醛、二美酮（5,5-二甲基环己烷-1,3-二酮）、β-酮酯和乙酸铵的一锅多组分反应，进行六氢喹啉的原子经济制备。催化剂通过包括傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）、振动样品磁力计（VSM）和透射电子显微镜（TEM）等多种技术进行了合成与表征。同时，使用响应面法（中央复合设计（CCD））对反应条件的优化进行了研究。