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1,4-Dihydropyridine

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1,4-Dihydropyridine
Skeletal formula of dihydropyridine
Ball-and-stick model of the dihydropyridine molecule
Names
Preferred IUPAC name 1,4-Dihydropyridine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
MeSH 1,4-dihydropyridine
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2Key: YNGDWRXWKFWCJY-UHFFFAOYSA-N
SMILES
  • C1C=CNC=C1
Properties
Chemical formula C
5H
7N
Molar mass 81.1158 g mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon, but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.

Properties and reactions

A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines are enamines, which otherwise tend to tautomerize or hydrolyze.

The dominant reaction of dihydropyridines is their ease of oxidation. In the case of dihydropyridines with hydrogen as the substituent on nitrogen, oxidation yields pyridines:

CH2(CH=CR)2NH → C5H3R2N + H2

The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:

CH2(CH=CR)2NR' → C5H3R2NR' + H

Hantzsch ester

Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine.

Hantzsch ester

See also

References

  1. "1,4-dihydropyridine - Compound Summary". Pubchem Compound. US: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 1 November 2011.
  2. Duburs, Gunãrs; Sausins, Alvils (1988). "Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions". Heterocycles. 27: 269. doi:10.3987/REV-87-370.
  3. Stout, David M.; Meyers, A. I. (1982). "Recent advances in the chemistry of dihydropyridines". Chemical Reviews. 82 (2): 223–243. doi:10.1021/cr00048a004.
  4. Lavilla, Rodolfo (2002). "Recent developments in the chemistry of dihydropyridines". Journal of the Chemical Society, Perkin Transactions 1 (9): 1141–1156. doi:10.1039/B101371H.
  5. Cheung, Lawrence L. W.; Styler, Sarah A.; Dicks, Andrew P. (2010). "Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure". Journal of Chemical Education. 87 (6): 628–630. Bibcode:2010JChEd..87..628C. doi:10.1021/ed100171g.

External links

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