| 词条 | Chalcone |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443514088 | Name = Chalcone[1] | ImageFile = Chalcone.svg | ImageSize = 180 | ImageAlt = Skeletal formula of chalcone | ImageFile1 = Chalcone 3D ball.png | ImageSize1 = 220 | ImageAlt1 = Ball-and-stick model of the chalcone molecule | PIN = Chalcone | SystematicName = (2E)-1,3-Diphenylprop-2-en-1-one | OtherNames = Chalkone Benzylideneacetophenone Phenyl styryl ketone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6921 | InChIKey = DQFBYFPFKXHELB-UHFFFAOYAP | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DQFBYFPFKXHELB-UHFFFAOYSA-N | CASNo = 94-41-7 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo2_Ref = {{cascite|changed|??}} | CASNo2 = 614-47-1 | CASNo2_Comment = ((E)-Chalcone) | PubChem = 637760 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 27618 | SMILES = O=C(C=Cc1ccccc1)c2ccccc2 | InChI = 1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H | MeSHName = |Section2={{Chembox Properties | C=15 | H=12 | O=1 | Appearance = | Density =1.071 g/cm3 | MeltingPtC = 55 to 57 | MeltingPt_notes = | BoilingPtC = 345 to 348 | Solubility = | MagSus = -125.7·10−6 cm3/mol }} Chalcone is an aromatic ketone and an enone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or chalconoids. Alternative names for chalcone include benzylideneacetophenone, phenyl styryl ketone, benzalacetophenone, β-phenylacrylophenone, γ-oxo-α,γ-diphenyl-α-propylene, and α-phenyl-β-benzoylethylene. Chemical propertiesChalcones have two absorption maximums at 280 nm and 340 nm.[2] Chemical reactionsSynthesisChalcones can be prepared by an aldol condensation between benzaldehyde and acetophenone in the presence of sodium hydroxide as a catalyst. This reaction can be carried out without any solvent as a solid-state reaction.[3] The reaction between substituted benzaldehydes and acetophenones can be used as an example of green chemistry in undergraduate education.[4] In a study investigating green syntheses, chalcones were synthesized from the same starting materials in high-temperature water (200 to 350 °C).[5] Substituted chalcones were also synthesised by piperidine-mediated condensation to avoid side reactions such as multiple condensations, polymerizations, and rearrangements.[6] Other reactionsAn example is the conjugate reduction of the enone by tributyltin hydride:[7] 3,5-Disubstituted 1H-pyrazoles can be produced from a suitably substituted chalcone by reaction with hydrazine hydrate in the presence of elemental sulfur[8] or sodium persulfate,[9] or by using a hydrazone in which case an azine is produced as a by-product. The specific case for formation of 3,5-diphenyl-1H-pyrazole from chalcone itself can be represented as:[10] Potential pharmacologyChalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.[11] Some 2′-amino chalcones are have been studied as potential antitumor agents.[12][13] See also
References1. ^Merck Index, 11th Edition, 2028 2. ^{{cite journal |DOI=10.1016/S0925-3467(02)00220-3 |title=Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display |journal=Optical Materials |volume=21 |pages=667–71 |year=2003 |last1=Song |first1=Dong-mee |last2=Jung |first2=Kyoung-Hoon |last3=Moon |first3=Ji-hye |last4=Shin |first4=Dong-Myung |bibcode=2003OptMa..21..667S}} 3. ^{{cite journal |doi=10.1039/P19900003207 |title=Aldol condensations in the absence of solvent: Acceleration of the reaction and enhancement of the stereoselectivity |journal=Journal of the Chemical Society, Perkin Transactions 1 |issue=11 |pages=3207–9 |year=1990 |last1=Toda |first1=Fumio |last2=Tanaka |first2=Koichi |last3=Hamai |first3=Koki }} 4. ^{{cite journal |doi=10.1021/ed081p1345 |title=Solvent-Free Synthesis of Chalcones |journal=Journal of Chemical Education |volume=81 |issue=9 |pages=1345 |year=2004 |last1=Palleros |first1=Daniel R |bibcode=2004JChEd..81.1345P }} 5. ^{{cite journal |doi=10.1039/b314622g |title=Kinetics of crossed aldol condensations in high-temperature water |journal=Green Chemistry |volume=6 |issue=4 |pages=227–31 |year=2004 |last1=Comisar |first1=Craig M |last2=Savage |first2=Phillip E }} 6. ^{{cite journal |doi=10.1002/jhet.268 |title=Piperidine mediated synthesis ofn-heterocyclic chalcones and their antibacterial activity |journal=Journal of Heterocyclic Chemistry |volume=47 |issue=1 |pages=81–84 |year=2009 |last1=Venkatesan |first1=P |last2=Sumathi |first2=S }} 7. ^{{cite journal |doi=10.1016/S0040-4039(00)72405-1 |title=Reaction of organotin hydrides with α,β-unsaturated ketones |journal=Tetrahedron Letters |volume=7 |issue=20 |pages=2221–5 |year=1966 |last1=Leusink |first1=A.J |last2=Noltes |first2=J.G }} 8. ^{{cite journal |doi=10.1002/jhet.5570450231 |title=New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating |journal=Journal of Heterocyclic Chemistry |volume=45 |issue=2 |pages=503–5 |year=2008 |last1=Outirite |first1=Moha |last2=Lebrini |first2=Mounim |last3=Lagrenée |first3=Michel |last4=Bentiss |first4=Fouad }} 9. ^{{cite journal |doi=10.3987/COM-13-12867 |title=One-Pot Synthesis of 3,5-Diphenyl-1H-pyrazoles from Chalcones and Hydrazine under Mechanochemical Ball Milling |journal=Heterocycles |volume=89 |pages=103–12 |year=2014 |last1=Zhang |first1=Ze |last2=Tan |first2=Ya-Jun |last3=Wang |first3=Chun-Shan |last4=Wu |first4=Hao-Hao }} 10. ^{{cite journal|title = Metal-free and FeCl3-catalyzed synthesis of azines and 3,5-diphenyl-1H-pyrazole from hydrazones and/or ketones monitored by high resolution ESI+-MS|year = 2018|journal = Indian Journal of Chemistry - Section B|volume = 57B|issue = 3|pages = 362–373|url = http://nopr.niscair.res.in/handle/123456789/43824|first = Jamal|last = Lasri|first2 = Ali I.|last2 = Ismail}} 11. ^{{cite journal |doi=10.2174/1568026617666170914160446 |pmid=28914193 |title=Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives |journal=Current Topics in Medicinal Chemistry |volume=17 |issue=28 |pages=3146–3169 |year=2017 |last1=Mahapatra |first1=Debarshi Kar |last2=Bharti |first2=Sanjay Kumar |last3=Asati |first3=Vivek }} 12. ^{{cite journal|last1=Xia|first1=Yi|last2=Yang|first2=Zheng-Yu|last3=Xia|first3=Peng|last4=Bastow|first4=Kenneth F.|last5=Nakanishi|first5=Yuka|last6=Lee|first6=Kuo-Hsiung|title=Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation|journal=Bioorganic & Medicinal Chemistry Letters|volume=10|issue=8|year=2000|pages=699–701|issn=0960894X|doi=10.1016/S0960-894X(00)00072-X}} 13. ^{{cite journal|last1=Santos|first1=Mariana B.|last2=Pinhanelli|first2=Vitor C.|last3=Garcia|first3=Mayara A.R.|last4=Silva|first4=Gabriel|last5=Baek|first5=Seung J.|last6=França|first6=Suzelei C.|last7=Fachin|first7=Ana L.|last8=Marins|first8=Mozart|last9=Regasini|first9=Luis O.|title=Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells|journal=European Journal of Medicinal Chemistry|volume=138|year=2017|pages=884–889|issn=02235234|doi=10.1016/j.ejmech.2017.06.049}} External links
2 : Chalconoids|Phenyl compounds |
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