1165-06-6

Basic information

• Product Name: Diethyl2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
• Synonyms: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-phenyl-, diethyl ester (6CI,7CI,8CI,9CI);1,4-Dihydro-2,6-dimethyl-4-phenyl-3,5-pyridinedicarboxylic acid diethyl ester;2,6-Dimethyl-3,5-bis(ethoxycarbonyl)-4-phenyl-1,4-dihydropyridine;2,6-Dimethyl-3,5-dicarbethoxy-4-phenyl-1,4-dihydropyridine;2,6-Dimethyl-3,5-diethoxycarbonyl-6-phenyl-1,4-dihydropyridine;3,5-Dicarbethoxy-2,6-dimethyl-4-phenyl-1,4-dihydropyridine; Diethyl1,4-dihydro-2,6-dimethyl-4-phenyl-3,5-pyridinedicarboxylate; Diethyl2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate; NSC 63467
• CAS NO: 1165-06-6
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.4
• Mol File: 1165-06-6.mol
• Article Data: 142

Chemical Properties

• Melting Point: 156-157 °C
• Boiling Point: 449.6°Cat760mmHg
• Flash Point: 225.7°C
• Appearance: /
• Density: 1.122g/cm³
• Vapor Pressure: 2.83E-08mmHg at 25°C
• Refractive Index: 1.529
• PKA: 3.12±0.70(Predicted)
• CAS DataBase Reference: Diethyl2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate(1165-06-6)
• EPA Substance Registry System: Diethyl2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate(1165-06-6)

Safety Data

• Hazardous Substances Data: 1165-06-6(Hazardous Substances Data)

Usage

General Description

"Diethyl2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate" is a specific organic compound, belonging to the 1,4-dihydropyridine (DHP) group of calcium channel blockers. It is structurally characterized by the presence of diethyl ester groups, two methyl groups, one phenyl group, and a 1,4-dihydropyridine ring. Like other DHPs, it is notably used in pharmaceutical applications due to its capacity to inhibit the influx of calcium ions into cardiac and vascular smooth muscle cells, thereby aiding in the treatment of conditions such as hypertension and angina. However, its specific biological behaviour along with physical properties such as melting point, boiling point, and solubility would have to be verified from scientific resources for concrete information.

InChI:InChI=1/C19H23NO4/c1-5-23-18(21)15-12(3)20-13(4)16(19(22)24-6-2)17(15)14-10-8-7-9-11-14/h7-11,17,20H,5-6H2,1-4H3

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• 64-17-5 ethanol 
• 75926-38-4 5-Benzylsulfanylcarbonyl-2,6-dimethyl-4-phenyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 57-13-6 urea 

Downstream Products

• 1539-44-2 2,6-dimethyl-4-phenyl-pyridine-3,5-dicarboxylic acid diethyl ester 

Relevant articles and documents

Accelerated Hantzsch electrospray synthesis with temporal control of reaction intermediates

Complex chemical reactions can occur in electrosprayed droplets on the millisecond time scale. The Hantzsch synthesis of 1,4-dihydropyridines was studied in this way using on-line mass spectral analysis to optimize conditions and characterize the product

An efficient and solvent-free one-pot synthesis of 1,4-dihydropyridines under microwave irradiation

An efficient synthesis of 1,4-dihydropyridines using lanthanum oxide as a catalyst from aldehydes, β-ketoester and ammonium acetate without solvent under the irradiation of microwave is described. Compared with the classical Hantzsch reaction, this new me

The multicomponent Hantzsch reaction: Comprehensive mass spectrometry monitoring using charge-tagged reagents

A novel strategy for the ESI-MS monitoring of reaction solutions involving the alternate use of permanently charge-tagged reagents has been used for comprehensive mass spectrometry monitoring of the multicomponent Hantzsch 1,4-dihydropyridine reaction. By placing a charge tag on either, or both, of the two key reactants, ion suppression effects for ESI were eliminated or minimized, and comprehensive detection of charge-tagged intermediates was achieved. The strategy allowed the trapping and characterization of the important intermediates in the mechanism for 1,4-dihydropyridine formation.

Photoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation

We herein report the photoinduced intermolecular umpolung addition of aromatic ketones/aldehydes with α,β-unsaturated esters via ketyl radical intermediates. Following an intramolecular transesterification, a variety of γ-lactone derivatives are readily accessed. Mechanistic investigations demonstrate the significant role of Hantzsch ester, which serves both as the electron and proton donor. This journal is

Research on heterocyclic compounds. XLIII. Synthetic studies on 1,4-dihydropyridine derivatives

In order to obtain N-benzyl-3,5-dicarbethoxy-2,6-dimethyl-4-phenyl-1,4-dihydropyridine 1 as a lead compound of pharmacological interest, the classical Hantzsch synthetic method and the modified Collie procedure were used. However, only a very low yield of

Unprecedented synthesis of hantzsch 1,4-dihydropyridines under biginelli reaction conditions

Hantzsch 1,4-dihydropyridines are synthesized in high yields by a one-pot cyclocondensation of aldehyde, β-ketoester, and urea on the surface of silica gel under microwave irradiation in solvent-free conditions.

Silica (NPs) supported Fe (III) as a reusable heterogeneous catalyst for the one-pot synthesis of 1, 4-dihydropyridines under mild conditions

A cheap and recyclable silica (NPs) supported Fe (III) was prepared as heterogeneous catalyst for the synthesis of various substituted 1,4-dihydropyridines via condensation of aldehydes with ethyl acetoacetate and ammonium acetate in ethanol. The products

g-C3N4@Ce-MOF Z-scheme heterojunction photocatalyzed cascade aerobic oxidative functionalization of styrene

A special composite of the cerium-based metal-organic framework (Ce-UiO-66) modified with graphitic carbon nitride nanosheets (g-C3N4) has been synthesized. In order to make a comparison, a series of composites comprising g-C3N4and Ce-MOF were synthesized as well. Their structural features were investigated using Fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (PXRD), sorption of nitrogen (BET and BJH), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), transmission electron microscopy (TEM), X-ray fluorescence spectroscopy (XRF) and diffuse reflectance UV-Vis spectroscopy (UV-Vis DRS) and electron spin resonance (ESR) techniques. According to the obtained results, it was found that nanosheets of mesoporous g-C3N4act as linkers between the cerium sites, playing a critical role in the formation of composites. In fact, the embedded g-C3N4nanoparticles in the Ce-MOF cause a new kind of meso-porosity. Moreover, the coordination of nitrogen atoms in the graphitic carbon nitride structure to cerium atoms of the crystal brings about substantial changes in the optical properties, increasing the photoreactivity. On the other hand, since there is a physical contact between Ce-UiO-66 and g-C3N4in the composite, the unaltered pore volume and optical properties lead to the formation of a physical mixture rather than a composite. The g-C3N4@Ce-MOF as a photocatalyst was employed in photocatalytic aerobic oxidative Hantzsch pyridine synthesis of styrene and indicated high performance under visible light. The stability and reusability of g-C3N4@Ce-MOF were also examined and showed high efficiency up to the 5th run. Besides, the PXRD and FT-IR analyses taken from the retrieved g-C3N4@Ce-MOF nanocomposite confirmed the catalyst stability after the completion of the cascade aerobic oxidative reaction. Despite the photocatalytic performance, the synergistic effect of open metal sites in the MOF as Lewis acid and nitrogen in g-C3N4have greatly improved the efficiency of the catalyst. Moreover, the study of the reaction mechanism using ESR indicates the positive effect of composite formation on the performance of the photocatalytic aerobic oxidation reaction by the superoxide radical (O2˙—), as a selective oxidant species.

Synthesis, characterization and cytotoxicity evaluation of a novel magnetic nanocomposite with iron oxide deposited on cellulose nanofibers with nickel (Fe3O4@NFC@ONSM-Ni)

A heterogeneous, magnetically recoverable nanocomposite, Fe3O4@NFC@ONSM-Ni(ii) was prepared by immobilization of a novel Ni(ii) Schiff base complex on Fe3O4@NFC nanoparticles followed by treatment with melamine. This trinuclear catalyst has been characterized using several analytical techniques including FT-IR, TEM, Fe-SEM, EDX, DLS, ICP, TGA, VSM, and XRD. It was used as an efficient catalyst for one-pot solvent-free synthesis of 1,4-dihydropyridine and poly-hydro quinoline derivatives through Hantzsch reaction. This catalyst showed remarkable advantage over previously reported catalysts due to suitable conditions, short reaction time, high efficiency and lower catalyst load and timely recovery of the magnetic catalyst. Moreover, the effects of Fe3O4@NFC@ONSM-Ni(ii) nanoparticles on thein vitroproliferation of human leukemia cell line (k562) and human breast cancer cells (MDA-MB-231) were investigated. The results of MTT and Hochest assays suggested that the nanoparticles could effectively inhibit the proliferation of these cancer cells in a time- and concentration-dependent manner.