Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

Base Information

• Chemical Name: Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• CAS No.: 1149-23-1
• Molecular Formula: C13H19NO4
• Molecular Weight: 253.298
• Hs Code.: 29333990
• European Community (EC) Number: 214-561-6
• NSC Number: 120573,3344
• UNII: GWN6123BUG
• DSSTox Substance ID: DTXSID80150895
• Nikkaji Number: J140.363J
• Wikipedia: Hantzsch_ester
• Wikidata: Q27279321
• ChEMBL ID: CHEMBL1521734,CHEMBL3194512
• Mol file: 1149-23-1.mol

Synonyms:2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine;2,6-dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridine;diethone;diludin;diludine;DM-DEOC-DHP;ethidin;etidin

Chemical Property of Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

Chemical Property:

• Appearance/Colour: white power
• Vapor Pressure: 4.01E-05mmHg at 25°C
• Melting Point: 176-183 °C
• Refractive Index: 1.489
• Boiling Point: 351.8 °C at 760 mmHg
• PKA: 3.50±0.70(Predicted)
• Flash Point: 166.6 °C
• PSA: 64.63000
• Density: 1.104 g/cm³
• LogP: 1.98270
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in organic solvents.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 253.13140809
• Heavy Atom Count: 18
• Complexity: 383

Purity/Quality:

99% ^*data from raw suppliers

3,5-Dicarboethoxy-2,6-dimethyl-1,4-dihydropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C(C1)C(=O)OCC)C)C
• Uses: 3,5-Dicarboethoxy-2,6-dimethyl-1,4-dihydropyridine is a dihydropyridine derivative that have been tested for antimicrobial activities. Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate is a hydrogen source in conjugate reduction and organocatalytic reductive amination. It is used as a hydrogen source in organocatalytic reductive amination and conjugate reduction.

Technology Process of Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

There total 32 articles about Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ethyl acetoacetate (141-97-9) → diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1149-23-1)

Guidance literature:

With ammonium acetate; In water; at 86 ℃; for 3h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00836

Reference yield: 98.0%

hexamethylenetetramine (100-97-0) + ethyl acetoacetate (141-97-9) → diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1149-23-1)

Guidance literature:

hexamethylenetetramine; ethyl acetoacetate; at 15 - 20 ℃; for 0.5h; Large scale;

With ethanolamine; at 30 - 70 ℃; for 2.5h; Large scale;

Reference yield: 92.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ammonium acetate (631-61-8,92206-38-7) + ethyl acetoacetate (141-97-9) → diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1149-23-1)

Guidance literature:

formaldehyd; ammonium acetate; ethyl acetoacetate; With cellulose sulfuric acid; In neat (no solvent); at 80 - 100 ℃;

With cellulose sulfuric acid; In neat (no solvent);

DOI:10.1016/j.bmcl.2012.05.003

upstream raw materials:

hexamethylenetetramine

ethyl acetoacetate

formaldehyd

ethyl aminocrotonate

Downstream raw materials:

3-methylcyclohexen-2-one

5-([4-[2-(4-(3-Nitrophenylsulfonyloxy)phenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione

5-(1-[4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]phenyl]ethyl)thiazolidine-2,4-dione

5-([4-[2-(4-Cyanophenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione

Refernces

• 1、 Illa, Giri Teja,Hazra, Sohan,Satha, Pardhasaradhi,Purohit, Chandra Shekhar. "Hydrogen-bonded molecular capsules: Probing the role of water molecules in capsule formation in modified cyclotricatechylene". . p. 4759 - 4765. Retrieved 2017.
• 2、 Lu,Bai,Wang,Yang,Li. "Ferric chloride hexahydrate: A convenient reagent for the oxidation of hantzsch 1,4-dihydropyridines". . p. 2625 - 2630. Retrieved 2001.
• 3、 Li, Zhifen,Qiao, Jun,Jia, Zhifang,Meng, Shuangming. "Synthesis of the pyridine hydrazones as metal-free artificial nucleases". . p. 1243 - 1244. Retrieved 2015.
• 4、 Grugel, Christian P.,Breit, Bernhard. "Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines". . p. 9672 - 9676. Retrieved 2019.
• 5、 Guo, Yan-Jun,Li, Yang,Zhang, Ping,Zhao, Yu-Rou,Zhou, Chao-Zheng. "Formic acid disproportionation into formaldehyde triggered by vanadium complexes with iridium catalysis under mild conditions inN-methylation". . p. 2918 - 2924. Retrieved 2021.
• 6、 Gutiérrez-Bonet, álvaro,Remeur, Camille,Matsui, Jennifer K.,Molander, Gary A.. "Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines". . p. 12251 - 12258. Retrieved 2017.
• 7、 Kellogg et al.. "-". . p. 5211. Retrieved 1969.
• 8、 Christiaens, Sylvain,Vantyghem, Xavier,Radoiu, Marilena,Eynde, Jean Jacques Vanden. "Batch and continuous flow preparation of hantzsch 1,4-dihydropyridines under microwave heating and simultaneous real- Time monitoring by raman spectroscopy. An exploratory study". . p. 9986 - 9998. Retrieved 2014.
• 9、 Orfanidou, Maria,Petsi, Marina,Zografos, Alexandros L.. "Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen". supporting information. p. 9172 - 9178. Retrieved 2021/11/30.