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1,4-Dihydropyridine

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1,4-Dihydropyridine

Ball-and-stick model of the dihydropyridine molecule

Names

Preferred IUPAC name

1,4-Dihydropyridine^[1]

Identifiers

CAS Number

3337-17-5^Y

3D model (JSmol)

Interactive image

ChemSpider

94619^Y

MeSH

1,4-dihydropyridine

PubChem CID

104822

UNII

7M8K3P6I89^Y

CompTox Dashboard(EPA)

DTXSID20274185

InChI

InChI=1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2^Y
Key: YNGDWRXWKFWCJY-UHFFFAOYSA-N^Y

SMILES

C1C=CNC=C1

Properties

Chemical formula

C
₅H
₇N

Molar mass

81.1158 g mol⁻¹

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is ^YN ?)

Infobox references

Chemical compound

1,4-Dihydropyridine (DHP) is anorganic compound with the formula CH₂(CH=CH)₂NH. The parent compound is uncommon,^[2] but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactorsNADH andNADPH are derivatives of 1,4-dihydropyridine.Dihydropyridine calcium channel blockers are a class ofL-type calcium channel blockers used in the treatment of hypertension. 1,2-Dihydropyridines are also known.^[3]^[4]

Properties and reactions

[edit]

A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines areenamines, which otherwise tend to tautomerize or hydrolyze.^{[citation needed]}

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

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

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

Hantzsch ester^[5]

References

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^"1,4-dihydropyridine - Compound Summary".Pubchem Compound. US: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved1 November 2011.
^Duburs, Gunãrs; Sausins, Alvils (1988)."Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions".Heterocycles.27: 269.doi:10.3987/REV-87-370.
^Stout, David M.; Meyers, A. I. (1982). "Recent advances in the chemistry of dihydropyridines".Chemical Reviews.82 (2):223–243.doi:10.1021/cr00048a004.
^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.
^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.