https://wiki.tiffa.net/w/index.php?action=history&feed=atom&title=1%2C4-Dihydropyridine 2026-04-20T07:02:15Z Revision history for this page on the wiki MediaWiki 1.43.0 https://wiki.tiffa.net/w/index.php?title=1,4-Dihydropyridine&diff=76332&oldid=prev 2023-11-15T12:04:55Z

<p>Created page with &quot;{{Chembox | Watchedfields = changed | verifiedrevid = 422213266 | ImageFileL1 = 1,4-Dihydropyridine.png | ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageSizeL1 = 80 | ImageAltL1 = Skeletal formula of dihydropyridine | ImageFileR1 = Dihydropyridine-3D-balls.png | ImageSizeR1 = 120 | ImageAltR1 = Ball-and-stick model of the dihydropyridine molecule | PIN = 1,4-Dihydropyridine&lt;ref&gt;{{Cite web|title = 1,4-dihydropyridine - Compound Summary|url = https://pubchem.ncbi.nlm...&quot;</p> <p><b>New page</b></p><div>{{Chembox<br /> | Watchedfields = changed<br /> | verifiedrevid = 422213266<br /> | ImageFileL1 = 1,4-Dihydropyridine.png<br /> | ImageFileL1_Ref = {{chemboximage|correct|??}}<br /> | ImageSizeL1 = 80<br /> | ImageAltL1 = Skeletal formula of dihydropyridine<br /> | ImageFileR1 = Dihydropyridine-3D-balls.png<br /> | ImageSizeR1 = 120<br /> | ImageAltR1 = Ball-and-stick model of the dihydropyridine molecule<br /> | PIN = 1,4-Dihydropyridine&lt;ref&gt;{{Cite web|title = 1,4-dihydropyridine - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=104822&amp;loc=ec_rcs|work = Pubchem Compound|publisher = National Center for Biotechnology Information|access-date = 1 November 2011|location = US|date = 27 March 2005|at = Identification and Related Records}}&lt;/ref&gt;<br /> |Section1={{Chembox Identifiers<br /> | CASNo = 3337-17-5<br /> | CASNo_Ref = {{cascite|correct|??}}<br /> | UNII_Ref = {{fdacite|correct|FDA}}<br /> | UNII = 7M8K3P6I89<br /> | PubChem = 104822<br /> | ChemSpiderID = 94619<br /> | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}<br /> | MeSHName = 1,4-dihydropyridine<br /> | SMILES = C1C=CNC=C1<br /> | StdInChI = 1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2<br /> | StdInChI_Ref = {{stdinchicite|correct|chemspider}}<br /> | StdInChIKey = YNGDWRXWKFWCJY-UHFFFAOYSA-N<br /> | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}<br /> }}<br /> |Section2={{Chembox Properties<br /> | Formula = {{Chem|C|5|H|7|N}}<br /> | MolarMass = 81.1158 g mol&lt;sup&gt;−1&lt;/sup&gt;<br /> }}<br /> }}<br /> <br /> &#039;&#039;&#039;1,4-Dihydropyridine&#039;&#039;&#039; (&#039;&#039;&#039;DHP&#039;&#039;&#039;) is an [[organic compound]] with the formula CH&lt;sub&gt;2&lt;/sub&gt;(CH=CH)&lt;sub&gt;2&lt;/sub&gt;NH. The parent compound is uncommon,&lt;ref&gt;{{cite journal |doi=10.3987/REV-87-370|title=Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions|year=1988|last1=Duburs|first1=Gunãrs|last2=Sausins|first2=Alvils|journal=Heterocycles|volume=27|page=269}}&lt;/ref&gt; 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|&lt;small&gt;L&lt;/small&gt;-type calcium channel]] blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.&lt;ref&gt;{{cite journal |doi=10.1021/cr00048a004|title=Recent advances in the chemistry of dihydropyridines|year=1982|last1=Stout|first1=David M.|last2=Meyers|first2=A. I.|journal=Chemical Reviews|volume=82|issue=2|pages=223–243}}&lt;/ref&gt;&lt;ref&gt;{{cite journal |doi=10.1039/B101371H|title=Recent developments in the chemistry of dihydropyridines|year=2002|last1=Lavilla|first1=Rodolfo|journal=Journal of the Chemical Society, Perkin Transactions 1|issue=9|pages=1141–1156}}&lt;/ref&gt;<br /> <br /> ==Properties and reactions==<br /> A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines are [[enamine]]s, which otherwise tend to tautomerize or hydrolyze.{{cn|date=June 2023}}<br /> <br /> The dominant reaction of dihydropyridines is their ease of oxidation. In the case of dihydropyridines with hydrogen as the substituent on nitrogen, oxidation yields [[pyridine]]s:<br /> :CH&lt;sub&gt;2&lt;/sub&gt;(CH=CR)&lt;sub&gt;2&lt;/sub&gt;NH → C&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;3&lt;/sub&gt;R&lt;sub&gt;2&lt;/sub&gt;N + H&lt;sub&gt;2&lt;/sub&gt;<br /> The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:<br /> :CH&lt;sub&gt;2&lt;/sub&gt;(CH=CR)&lt;sub&gt;2&lt;/sub&gt;NR&#039; → C&lt;sub&gt;5&lt;/sub&gt;H&lt;sub&gt;3&lt;/sub&gt;R&lt;sub&gt;2&lt;/sub&gt;NR&#039; + H&lt;sup&gt;−&lt;/sup&gt;<br /> <br /> ==See also==<br /> [[File:HantzschEster.svg|thumb|left|Chemical structure of Hantzsch&#039;s ethyl ester, a well-known dihydropyridine.]]<br /> * [[Dihydropyridine calcium channel blockers]]<br /> * [[Hantzsch pyridine synthesis|Hantzsch ester]]&lt;ref&gt;{{cite journal |doi=10.1021/ed100171g|title=Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure|year=2010|last1=Cheung|first1=Lawrence L. W.|last2=Styler|first2=Sarah A.|last3=Dicks|first3=Andrew P.|journal=Journal of Chemical Education|volume=87|issue=6|pages=628–630|bibcode=2010JChEd..87..628C}}&lt;/ref&gt;<br /> * [[Dihydropyridine receptor]]<br /> {{clear}}<br /> <br /> ==References==<br /> <br /> {{Reflist}}<br /> <br /> ==External links==<br /> * {{MeshName|Dihydropyridines}}<br /> <br /> {{二次利用|date=31 July 2023}}<br /> [[Category:Dihydropyridines| ]]</div>

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