1156-64-5

Basic information

• Product Name: diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate
• Synonyms: diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate;1,4-Dihydro-2,6-dimethyl-4-propyl-3,5-pyridinedicarboxylic acid diethyl ester;4-Propyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester;2,6-dimethyl-4-propyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester;diethyl 2,6-dimethyl-4-propyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS NO: 1156-64-5
• Molecular Formula: C₁₆H₂₅NO₄
• Molecular Weight: 295.374
• EINECS: 214-592-5
• Mol File: 1156-64-5.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 389.1°Cat760mmHg
• Flash Point: 189.1°C
• Appearance: /
• Density: 1.042g/cm³
• Vapor Pressure: 2.92E-06mmHg at 25°C
• Refractive Index: 1.477
• CAS DataBase Reference: diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate(1156-64-5)
• EPA Substance Registry System: diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate(1156-64-5)

Safety Data

• Hazardous Substances Data: 1156-64-5(Hazardous Substances Data)

Usage

Description

Diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate, also known as dipropyldopamine, is a chemical compound that functions as an antioxidant and a vasodilator. It is characterized by its ability to scavenge free radicals and reduce oxidative stress, which contributes to the maintenance of cardiovascular and nervous system health.

Uses

Used in Cardiovascular Applications:
Diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate is used as a therapeutic agent for the treatment of cardiovascular diseases. It helps in protecting the heart and blood vessels by reducing oxidative stress and promoting vasodilation, which improves blood flow and overall cardiovascular health.
Used in Cerebrovascular Applications:
In the field of cerebrovascular health, diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate is utilized as a neuroprotective agent. Its antioxidant properties aid in safeguarding the nervous system and may contribute to the prevention or treatment of cerebrovascular disorders.
Used in Neurodegenerative Disease Treatment:
Diethyl 1,4-dihydro-2,6-dimethyl-4-propylpyridine-3,5-dicarboxylate is being studied for its potential use in the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's. Its antioxidant and neuroprotective properties make it a promising candidate for managing these conditions and potentially slowing their progression.

InChI:InChI=1/C16H25NO4/c1-6-9-12-13(15(18)20-7-2)10(4)17-11(5)14(12)16(19)21-8-3/h12,17H,6-9H2,1-5H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 123-72-8 butyraldehyde 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 140429-20-5 N-(1-chlorobutyl)pyridinium chloride 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 506-87-6 ammonium carbonate 
• 109-73-9 N-butylamine 

Downstream Products

• 5449-45-6 2-biphenyl-4-yl-hexanoic acid 
• 16002-93-0 (E)-1-phenyl-1-pentene 
• 942-92-7 caprophenone 

Relevant articles and documents

The accelerated preparation of 1,4-dihydropyridines using microflow reactors

The synthesis of 1,4-dihydropyridines was performed in a continuous-flow microreactor. Elevated temperatures accelerated the reaction rate significantly allowing the reaction to be finished in minutes (6-11 min). Different 1,4-dihydropyridines were prepared in good to excellent isolated yields (45-88% yield). The method was amenable to the preparation of daropidine, a calcium channel blocker which is currently in clinical phase 3 trials.

Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation

Histidine (His) carries a unique heteroaromatic imidazole side chain and plays irreplaceable functional roles in peptides and proteins. Existing strategies for site-selective histidine modification predominantly rely on the N-substitution reactions of the moderately nucleophilic imidazole group, which inherently suffers from the interferences from lysine and cysteine residues. Chemoselective modification of histidine remains one of the most difficult challenges in peptide chemistry. Herein, we report peptide modification via radical-mediated chemoselective C-H alkylation of histidine using C4-alkyl-1,4-dihydropyridine (DHP) reagents under visible-light-promoted conditions. The method exploits the electrophilic reactivity of the imidazole ring via a Minisci-type reaction pathway. This method exhibits an exceptionally broad scope for both peptides and DHP alkylation reagents. Its utility has been demonstrated in a series of important peptide drugs, complex natural products, and a small protein. Distinct from N-substitution reactions, the unsubstituted nitrogen groups of the modified imidazole ring are conserved in the C-H alkylated products.

Poly(vinylimidazolum acetic acid)-entrapped nanozeolite: efficient heterogeneous catalyst for synthesis of polyhydroquinolines and 1,4-dihydropyridines

An effective method for synthesis of substituted 1,4-dihydropyridines and polyhydroquinoline derivatives by Hantzsch reaction using poly(ionic liquid)-based nanozeolite (NZ@PIL-COOH) catalyst under simple conditions is described. The new solid acid catalyst was prepared by polymerization of 3-carboxymethyl-1-vinylimidazolium in presence of modified nanozeolite, and characterized by Fourier-transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD) analysis, and transmission electron microscopy (TEM). The resulting heterogeneous catalyst displayed high catalytic performance under mild reaction condition in short reaction time. The catalyst was recycled eight times without any loss in reactivity or yield.