Diethyl 4-(p-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

Base Information

• Chemical Name: Diethyl 4-(p-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate
• CAS No.: 10354-30-0
• Molecular Formula: C19H23NO5
• Molecular Weight: 345.395
• DSSTox Substance ID: DTXSID001131371
• Nikkaji Number: J557.618K
• ChEMBL ID: CHEMBL1825008,CHEMBL3210360
• Mol file: 10354-30-0.mol

Synonyms:10354-30-0;diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate;Diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate;Diethyl 4-(p-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-4-(4-hydroxyphenyl)-2,6-dimethyl-, 3,5-diethyl ester;SR-01000367474;SMR000054558;Oprea1_118159;Oprea1_325726;CBDivE_010461;MLS000104625;SCHEMBL7368284;CHEMBL1825008;CHEMBL3210360;DTXSID001131371;HMS2307L15;STK387360;AKOS000274053;AB00076217-01;SR-01000367474-1;SR-01000367474-2;2,6-dimethyl-4-(4-hydroxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester;3,5-Diethyl 1,4-dihydro-4-(4-hydroxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate;Diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate #;diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxyl ate

Chemical Property of Diethyl 4-(p-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

Chemical Property:

• PSA: 84.86000
• LogP: 3.08200
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 345.15762283
• Heavy Atom Count: 25
• Complexity: 545

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C(C1C2=CC=C(C=C2)O)C(=O)OCC)C)C

Technology Process of Diethyl 4-(p-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

There total 5 articles about Diethyl 4-(p-hydroxyphenyl)-2,6-dimethyl-1,4-dihydro-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: 97.0%

ethyl acetoacetate (141-97-9) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 4-(4-hydroxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester (10354-30-0)

Guidance literature:

With ammonium acetate; In neat (no solvent); at 65 ℃; for 0.333333h; Catalytic behavior;

DOI:10.1039/d1ra01256h

Reference yield: 93.0%

ammonium acetate (631-61-8,92206-38-7) + ethyl acetoacetate (141-97-9) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 4-(4-hydroxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester (10354-30-0)

Guidance literature:

With iron supported on copper/Zeolite Socony Mobil-5 nanocatalyst; In water; at 20 ℃; Sonication;

DOI:10.1007/s13738-015-0734-5

Reference yield: 86.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + 3-Oxo-butaneperoxoic acid ethyl ester → 4-(4-hydroxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester (10354-30-0)

Guidance literature:

With ammonium acetate; In neat (no solvent); at 60 ℃; for 0.333333h;

DOI:10.1039/c3ta12476b

upstream raw materials:

ethyl acetoacetate

4-hydroxy-benzaldehyde

ethyl aminocrotonate

ammonium acetate

Downstream raw materials:

5-(4-hydroxyphenyl)-3-methylcyclohex-2-enone

diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

2,6-Dimethyl-4-(4-oxiranylmethoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

diethyl 4-(4-(2-ethoxy-2-oxoethoxy)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Refernces

• 1、 Simeonov,Afonso, Carlos A. M.. "Basicity and stability of urea deep eutectic mixtures". . p. 5485 - 5490. Retrieved 2016.
• 2、 Tu, Shu-Jiang,Zhou, Jian-Feng,Cai, Pei-Jun,Wang, Hai,Feng, Jun-Cai. "A convenient ferric chloride catalyzed synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones under microwave irradiation". . p. 147 - 151. Retrieved 2002.
• 3、 Taheri, Narges,Heidarizadeh, Fariba,Kiasat, Alireza. "A new magnetically recoverable catalyst promoting the synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives via the Hantzsch condensation under solvent-free conditions". . p. 481 - 487. Retrieved 2017.
• 4、 Tamaddon, Fatemeh,Ghazi, Somayeh. "Urease: A highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1,4-dihydropyridines from the in situ formed ammonia". . p. 63 - 67. Retrieved 2015.
• 5、 Murthy,Rajack, Abdul,Taraka Ramji,Jeson Babu,Praveen, Ch.,Aruna Lakshmi. "Design, solvent free synthesis, and antimicrobial evaluation of 1,4 dihydropyridines". . p. 6016 - 6023. Retrieved 2012.
• 6、 Priede, Elina,Zicmanis, Andris. "One-Pot Three-Component Synthesis of Hantzsch 1,4-Dihydropyridines Promoted by Dimethyl Phosphate Ionic Liquids". . p. 1095 - 1103. Retrieved 2015.
• 7、 Bajaj,Mahodaya,Tekade,Patil,Kukade, Suraj D.. "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". . p. 546 - 549. Retrieved 2017.
• 8、 Debache, Abdelmadjid,Boulcina, Raouf,Belfaitah, Ali,Rhouati, Salah,Carboni, Bertrand. "One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid catalyzed Hantzsch three-component reaction". . p. 509 - 512. Retrieved 2008.
• 9、 Allahresani, Ali,Mohammadpour Sangani, Mehri,Nasseri, Mohammad Ali. "CoFe2O4@SiO2-NH2-CoII NPs catalyzed Hantzsch reaction as an efficient, reusable catalyst for the facile, green, one-pot synthesis of novel functionalized 1,4-dihydropyridine derivatives". . . Retrieved 2020.
• 10、 Ananda Kumar, T. Durai,Mohan,Subrahmanyam,Satyanarayana. "Comparative study of catalytic potential of TBAB, BTEAC, and CTAB in one-pot synthesis of 1,4-dihydropyridines under aqueous medium". . p. 574 - 582. Retrieved 2014.