Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate

Base Information

• Chemical Name: Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate
• CAS No.: 67035-22-7
• Molecular Formula: C17H16N2O6
• Molecular Weight: 344.324
• European Community (EC) Number: 620-752-9
• UNII: OR3W8GT1C8
• DSSTox Substance ID: DTXSID9052347
• Nikkaji Number: J331.420K
• Wikidata: Q63395257
• ChEMBL ID: CHEMBL1573
• Mol file: 67035-22-7.mol

Synonyms:2,6-dimethyl-4-(ortho-nitrophenyl)-3,5-pyridinedicarboxylic aciddimenthyl ester;4-(2'-nitrophenyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid dimethyl ester;4-(2-nitrophenyl)-3,5-bis(carboxymethyl)-2,6-dimethylpyridine;B 4759;DDNPC;dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate

Chemical Property of Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate

Chemical Property:

• Vapor Pressure: 4.54E-08mmHg at 25°C
• Melting Point: 100-105oC
• Boiling Point: 443.7°Cat760mmHg
• PKA: 1.55±0.29(Predicted)
• Flash Point: 222.1°C
• PSA: 111.31000
• Density: 1.284g/cm³
• LogP: 3.37000
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 344.10083623
• Heavy Atom Count: 25
• Complexity: 492

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dehydro Nifedipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=C(C(=N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
• Description: Dehydro nifedipine is an active metabolite of nifedipine , a calcium channel blocker present in formulations used to treat hypertension and angina. Dehydro nifedipine is formed when nifedipine is metabolized by the cytochrome P450 (CYP) isomers CYP3A4 and CYP3A5. Dehydro nifedipine inhibits glucose uptake in PC-12 cells with an IC50 value of 130 μM.
• Uses: Oxidized nifedipine has been used for apoptotic signaling studies in dopaminergic neurons. The main Nifedipine metabolite in human plasma

Technology Process of Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate

There total 15 articles about Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-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: 96.0%

nifedipine (21829-25-4) → nifedipine (67035-22-7)

Guidance literature:

With tert.-butylhydroperoxide; iron(III)phthalocyanine chloride; acetic acid; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.bmc.2008.09.004

Reference yield: 94.0%

nifedipine (21829-25-4) → dimethyl 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate (50428-14-3) + nifedipine (67035-22-7)

Guidance literature:

In chloroform; Product distribution; Mechanism; Irradiation; addition of sodium benzoate; different light conditions;

Reference yield: 22.0%

nifedipine (21829-25-4) → dimethyl 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate (50428-14-3) + nifedipine (67035-22-7) + 5,6-Dihydro-2,4-dimethyl-6-hydroxy-5-oxo-3,6-diazaphenanthren-1-carbonsaeuremethylester (88434-71-3) + trans-2,2'-bis<2,6-dimethyl-3,5-bis(methoxycarbonyl)pyridine-4-yl>azoxybenzene

Guidance literature:

In methanol; at 20 ℃; for 4383h; Title compound not separated from byproducts; Irradiation;

DOI:10.1023/B:RUCB.0000012367.57360.18

upstream raw materials:

nifedipine

acetoacetic acid methyl ester

2-nitro-benzaldehyde

methyl 3-aminocrotonate

Downstream raw materials:

2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylic acid

Oxidized Nifedipine Monomethylester

2-Methyl-4-(2-nitrophenyl)-5-oxo-5,7-dihydrofuro<3,4-b>pyridin-3-carbonsaeuremethylester

Refernces

• 1、 Fang, Xiaoni,Zhang, Peng,Qiao, Liang,Feng, Xiaoyan,Zhang, Xiangmin,Girault, Hubert H.,Liu, Baohong. "Efficient drug metabolism strategy based on microsome-mesoporous organosilica nanoreactors". . p. 10870 - 10876. Retrieved 2014.
• 2、 Riemer, Daniel,Schilling, Waldemar,Goetz, Anne,Zhang, Yu,Gehrke, Sascha,Tkach, Igor,Hollóczki, Oldamur,Das, Shoubhik. "CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies". . p. 11679 - 11687. Retrieved 2018/11/23.
• 3、 -. "N3,N6-BIS(2-(5-METHOXY-1H-INDOLE-3-YL)ETHYL)-2,6-DIMETHYL-4-(2-NITROPHENYL)PYRIDINE-3,5-DICARBOXAMIDE AND USE THEREOF IN THE FIELD OF NEUROTOXICITY". Page/Page column 4; 5. . Retrieved 2017/08/21.