methyl 4‐(3‐bromophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate | 299947-39-0

• 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‐(3‐bromophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate
• 英文别名: ethyl 4-(3-bromo-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；methyl 4-(3-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；methyl 4-(3-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,7,8-pentahydroquinoline-3-carboxylate；methyl 4-(3-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 299947-39-0
• 化学式: C₂₀H₂₂BrNO₃
• 分子量: 404.304
• InChiKey: QKMSODBVRKUPMX-UHFFFAOYSA-N

物化性质

• 沸点：
  503.3±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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

• 作为反应物：
  描述：

  methyl 4‐(3‐bromophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate 、 苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.17h， 生成 Methyl 2,7,7-trimethyl-5-oxo-4-(3-phenylphenyl)-1,4,6,8-tetrahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and SAR of b-Annulated 1,4-Dihydropyridines Define Cardiomyogenic Compounds as Novel Inhibitors of TGFβ Signaling

  摘要：

  A medium-throughput murine embryonic stem cell (mESC)-based high-content screening of 17000 small molecules for cardiogenesis led to the identification of a b-annulated 1,4-dihydropyridine (1,4-DHP) that inhibited transforming growth factor beta (TGF beta)/Smad signaling by clearing the type II TGF beta receptor from the cell surface. Because this is an unprecedented mechanism of action, we explored the series' structure-activity relationship (SAR) based on TGF beta inhibition, and evaluated SAR aspects for cell-surface clearance of TGF beta receptor II (TGFBR2) and for biological activity in mESCs. We determined a pharmacophore and generated 1,4-DHPs with IC(50)s for TGF beta inhibition in the nanomolar range (e.g., compound. 28, 170 nM). Stereochemical consequences of a chiral center at the 4-position was evaluated, revealing 10- to 15-fold more potent TGF beta inhibition for the (+)- than the (-) enantiomer. This stereopreference was not observed for the low level inhibition against Activin A signaling and was reversed for effects on calcium handling in HL-1 cells.

  DOI：

  10.1021/jm301144g
• 作为产物：
  描述：

  间溴苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 乙酰乙酸甲酯 在 ammonium acetate 、 chitosan 作用下， 反应 0.15h， 以80%的产率得到methyl 4‐(3‐bromophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐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

• 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
• 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。
• Sulfuric acid heterogenized on magnetic Fe₃ O₄ nanoparticles: A new and efficient magnetically reusable catalyst for condensation reactions
  作者：Lotfi Shiri、Setare Zarei、Mosstafa Kazemi、Davood Sheikh

  DOI：10.1002/aoc.3938

  日期：2018.1

  Immobilized sulfuric acid on magnetic Fe3O4 nanoparticles (Fe3O4 MNPs‐OSO3H) as a new solid acid nanocomposite was successfully synthesized and its catalytic activity in a series of condensation reactions was studied. High catalytic activity, simple separation from reaction mixture by an external magnet and good reusability are several eco‐friendly advantages of this catalytic system. It is noteworthy

  成功地合成了固定在磁性Fe 3 O 4纳米颗粒上的硫酸（Fe 3 O 4 MNPs-OSO 3 H）作为一种新型固体酸纳米复合材料，并研究了其在一系列缩合反应中的催化活性。高催化活性，通过外部磁体与反应混合物的简单分离以及良好的可重复使用性是该催化系统的多项环保优势。值得注意的是，该催化体系适用于广泛范围的芳族醛，并且在温和的条件下以良好或优异的收率获得了所需的产物。从环境的角度来看，使用生态友好型溶剂也使该合成方案理想且引人入胜。
• Sucrose chelated auto combustion synthesis of BiFeO ₃ nanoparticles: Magnetically recoverable catalyst for the one‐pot synthesis of polyhydroquinoline
  作者：Harminder Singh、Nidhi Garg、Priya Arora、Jaspreet Kaur Rajput、Jigyasa

  DOI：10.1002/aoc.4357

  日期：2018.6

  synthesized materials. The BiFeO3 nanoparticles so obtained were employed as heterogeneous catalyst for the synthesis of polyhydroquinoline derivatives. All the polyhydroquinoline derivatives were characterized by Fourier transform infrared spectroscopy (FT‐IR) and Nuclear magnetic resonance spectroscopy (1H NMR). For the very first time ever we have used BiFeO3 as a recyclable magnetic nanocatalyst in the

  通过自动燃烧合成了蔗糖螯合的铋铁氧体（BiFeO 3）纳米颗粒作为新型非均相催化剂。已采用不同的煅烧温度（150°C，450°C，550°C，650°C，750°C和850°C）获得单相BiFeO 3纳米粒子。钙钛矿结构的形成和有机相（蔗糖）的消失是通过傅立叶变换红外光谱（FT-IR）获得的。相的确定和结构表征是通过粉末X射线衍射（XRD）进行的。通过振动样品磁力计（VSM）分析了磁性，而表面积/孔体积是通过Brunauer-Emmett-Teller（BET）获得的。透射电子显微镜（TEM）分析了颗粒的大小和形态。通过热重分析（TGA）研究热稳定性，并通过X射线光电子能谱（XPS）确定组成元素。拉曼光谱证实了合成材料的钙钛矿结构。BiFeO 3如此获得的纳米颗粒用作合成多氢喹啉衍生物的非均相催化剂。所有聚氢喹啉衍生物均通过傅里叶变换红外光谱（FT-IR）和核磁共振光谱（1 H NMR）进