1539-56-6

Basic information

• Product Name: diethyl 4-(2-phenylvinyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• Synonyms: diethyl 4-(2-phenylvinyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS NO: 1539-56-6
• Molecular Weight: 355.434
• Mol File: 1539-56-6.mol

Chemical Properties

• CAS DataBase Reference: diethyl 4-(2-phenylvinyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 4-(2-phenylvinyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate(1539-56-6)
• EPA Substance Registry System: diethyl 4-(2-phenylvinyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate(1539-56-6)

Safety Data

• Hazardous Substances Data: 1539-56-6(Hazardous Substances Data)

Upstream product

• 141-97-9 ethyl acetoacetate 
• 104-55-2 3-phenyl-propenal 
• 57-13-6 urea 
• 631-61-8 ammonium acetate 

Downstream Products

• 943331-65-5 diethyl 2,6?dimethyl?4?cinnamylpyridine?3,5?dicarboxylate 
• 1539-43-1 diethyl 4-(2-phenylethenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate 
• 1149-24-2 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester 

Relevant articles and documents

An efficient one-step synthesis of 1,4-dihydropyridines via a triphenylphosphine-catalyzed three-component Hantzsch reaction under mild conditions

An efficient one-step synthesis of 1,4-dihydropyridines in good to excellent yields via the triphenylphosphine-catalyzed Hantzsch three-component reaction of an aromatic aldehyde, ethyl acetoacetate and ammonium acetate is described.

Dual solvent-catalyst role of deep eutectic solvents in Hantzsch dihydropyridine synthesis

Deep eutectic solvents are a class of new generation green solvents formed from two or more components, which furnish a new homogeneous liquid phase with lower melting point than the individual components. Here, for the first time, dual role of DES as cat

MIL-101-SO3H metal-organic framework as a Br?nsted acid catalyst in Hantzsch reaction: An efficient and sustainable methodology for one-pot synthesis of 1,4-dihydropyridine

A straightforward and efficient methodology for the one-pot multicomponent synthesis of 1,4-dihydropyridine has been developed using MIL-101-SO3H metal-organic framework as a solid Br?nsted acid. The presence of the uniformly distributed Br?nsted acidic sulfonic acid sites throughout the framework and the high stability bestow the catalyst with excellent reactivity towards the synthesis of 1,4-dihydropyridine under simple reaction conditions using renewable ethanol as the solvent. The present methodology tolerates various functional groups and allows the synthesis of 1,4-dihydropyridine derivatives in good to excellent yields through Hantzsch reaction. The developed methodology proceeds under mild conditions, avoids corrosive reagents and special reaction conditions, and is amenable to gram scale synthesis. The sustainable nature of the catalyst was proved by the easy recovery and the reusability of the catalyst, as it was reused several times without loss in activity, which was confirmed from the FTIR, PXRD and SEM analyses of the reused catalyst.

Synergistic catalytic effect between ultrasound waves and pyrimidine-2,4-diamine-functionalized magnetic nanoparticles: Applied for synthesis of 1,4-dihydropyridine pharmaceutical derivatives

A convenient strategy for synthesis of the various derivatives of 1,4-dihydropyridine (1,4-DHP), as one of the most important pharmaceutical compounds, is presented in this study. For this purpose, firstly, magnetic iron oxide nanoparticles (Fe3O4 NPs) were fabricated and suitably coated by silica network (SiO2) and trimethoxy vinylsilane (TMVS). Then, their surfaces were well functionalized with pyrimidine-2,4-diamine (PDA) as the main active sites for catalyzing the synthesis reactions. In this regard, the performance of three different methods including reflux, microwave (MW) and ultrasound wave (USW) irradiations have been comparatively monitored via studying various analyses on the fabricated nanocatalyst (Fe3O4/SiO2-PDA). Concisely, high efficiency of the USW irradiation (in an ultrasound cleaning bath with a frequency of 50 kHz and power of 250 W/L) has been well proven through the investigation of the main factors such as excellent surface-functionalization, core/shell structure conservation, particle uniformity, close size distribution of the particles, and great inhibition of the particle aggregation. Then, the effectiveness of the USW irradiation as a promising co-catalyst agent has been clearly demonstrated in the 1,4-DHP synthesis reactions. It has been concluded that the USW could provide more appropriate conditions for activation of the catalytic sites of Fe3O4/SiO2-PDA NPs. However, high reaction yields (89%) have been obtained in the short reaction times (10 min) due to the substantial synergistic effect between the presented nanocatalyst and USW.

Silica-supported ceric ammonium nitrate (CAN): a simple, mild and solid-supported reagent for quickest oxidative aromatization of Hantzsch 1,4-dihydropyridines

An efficient and environmentally benign methodology for the oxidative aromatization of 1,4-dihydropyridines to their corresponding pyridine derivatives is developed. The oxidative aromatization of 1,4-dihydropyridines was explored using silica-supported ceric ammonium nitrate as catalyst in CH3CN with or without sonication at room temperature. This supported catalyst acts as a more efficient oxidising reagent and offers several advantages over other reported reagents in terms of reaction time and yields. The supported reagent is found to be more efficient and selective when compared with its unsupported form. The Belousov–Zhabotinskii reaction was not observed in present reaction. The dealkylation observed in case of 4-n-alkyl/n-alkenyl with other oxidising agents is also not observed in the present case.

Facile template-free route to fabricate core–shell Fe3O4@PANI-SO3H urchin-like nanoparticles as reusable catalyst for Hantzsch reaction: change morphology upon sulfonation

Abstract: This paper describes a novel and effective approach to fabricate the core–shell Fe3O4@PANI-SO3H urchin-like morphology in a self-assembly method as nano-magnetic solid acid catalyst. The Fe3O4@PANI microspheres were synthesized via an in situ surface polymerization of aniline monomer in an acidic condition, using ammonium persulfate as the oxidant. It was found that upon sulfonation of polyaniline (PANI), the morphology changes to morphology similar to urchin confirming the transmission electron microscopy and field emission scanning electron microscopy results. The as-prepared solid acid catalyst was also carefully analyzed by energy-dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis and vibrating sample magnetometry. This new magnetic core–shell material was shown to have high catalytic performance for one–pot synthesis of 1,4-dihydropyridine derivatives. In addition, the catalyst can be easily separated using an external magnet. Recyclability and reusability for several runs, facile accessibility, and simple handling are the merits of this magnetic-heterogeneous acid catalyst. Graphical Abstract: [Figure not available: see fulltext.].

CAN mediated mechanochemical synthesis of substituted pyridine derivatives

A simple, green and cost-effective protocol has been devised for the synthesis of 4-substituted-2,6-dimethyl-3,5-pyridinecarboxylates from Hantzsch-type 1,4-dihydropyridines via rapid oxidation in excellent yields using 1.5 equivalent of ceric ammonium nitrate within 15 minutes in solvent-free conditions. The method was able to furnish the products in excellent yields. The products obtained were characterized by their NMR and melting points data.

Fe3O4@SiO2 supported aza-crown ether complex cation ionic liquids: preparation and applications in organic reactions

A series of aza-crown ether ionic liquids supported on magnetic Fe3O4@SiO2 core-shell particles were designed, synthesized and characterized by elemental analysis, TEM, TG and FT-IR. These new aza-crown ether complex cation ionic liquids were utilized as heterogeneous acidic catalysts in Friedel-Crafts alkylation and Hantzsch reaction in good yields under convenient reaction conditions. Moreover, these magnetic particle supported IL catalysts could be readily recovered by an external magnet and reused five times without obvious loss of activity.

Sulfated polyborate: An efficient and reusable catalyst for one pot synthesis of Hantzsch 1,4-dihydropyridines derivatives using ammonium carbonate under solvent free conditions

A simple and efficient method for the synthesis of four-component 1,4-dihydropyridines of various aldehydes, β-ketoesters and ammonium carbonate catalyzed by sulfated polyborate with high yields under a solvent free condition at 90?°C is described. The key advantages of the present method are high yields, short reaction time, solvent free condition, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards.

Synthesis of diethyl 4-(phenyl-substituted)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates catalyzed by CoCl2/K-10 montmorillonite in water and their antimicrobial activity

A simple and efficient method of one pot synthesis of 1,4-dihydropyridine by three components reaction of aromatic aldehydes with 1,3-dicarbonyl compound, ammonium acetate and catalytic amount of CoCl2 based on the Hantszch reaction is developed. The process is catalysis by an inexpensive catalyst in water medium, gives high yield of products and involves no volatile organic solvents. Some synthesized compounds demonstrated antimicrobial activity.