| Revision as of 10:50, 11 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 426291372 |
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| verifiedrevid = 460110678 |
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|ImageFileL1=Cyclopentenone.png |
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| ImageFileL1 =Cyclopentenone.png |
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|ImageSizeL1=80px |
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| ImageSizeL1 =80px |
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|ImageFileR1=Cyclopentenone3d.png |
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| ImageFileR1 =Cyclopentenone3d.png |
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|ImageSizeR1=110px |
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| ImageSizeR1 =110px |
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|IUPACName= 2-Cyclopenten-1-one |
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| PIN = Cyclopent-2-en-1-one |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 12999 |
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| ChemSpiderID = 12999 |
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| SMILES = C1CC(=O)C=C1 |
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| SMILES = C1CC(=O)C=C1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2 |
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| StdInChI =1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BZKFMUIJRXWWQK-UHFFFAOYSA-N |
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| StdInChIKey = BZKFMUIJRXWWQK-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=930-30-3 |
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| ChEMBL = 52190 |
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| CASNo =930-30-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=13588 |
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| UNII = Q0U2IGF9CK |
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| ChEBI = 141550 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 52190 |
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| PubChem =13588 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=5 | H=6 | O=1 |
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| Formula=C<sub>5</sub>H<sub>6</sub>O |
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| MolarMass=82.04 g·mol<sup>−1</sup> |
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| Density = 0.98 g·mL<sup>−1</sup> |
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| BoilingPtC = 150 |
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| Density = 0.98 g·mL<sup>−1</sup> |
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| Solubility = almost insoluble in ] }} |
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| BoilingPt = 150 °C |
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|Section3={{Chembox Hazards |
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| Solubility = almost insoluble in ] }} |
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| MainHazards = Harmful |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Harmful |
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| FlashPtC = 42 |
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| FlashPt = 42 °C |
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'''2-Cyclopentenone''' is the ] with the ] {{chem2|(CH2)2(CH)2CO}}. 2-Cyclopentenone contains two functional groups, a ketone and an alkene. It is a colorless liquid. Its isomer, 3-cyclopentenone is less commonly encountered. |
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'''Cyclopentenone''' is a ] with ] {{carbon}}<sub>5</sub>{{hydrogen}}<sub>6</sub>{{oxygen}} and ] 930-30-3. It is structurally similar to ], with the additional feature of ] in the ring system. Cyclopentenone belongs to the ] (]s which have one or more ]) class of compounds and is also a ] (it possesses a ] functional group). It is a liquid at room temperature with a boiling point of 150 °C. It has been isolated from pressure-cooked pork ] by simultaneous steam ] and continuous ].<ref name="isol">{{cite|author = Mussinan,C.J.; Walradt, J.P.|journal = ]|year = 1974|volume = 22|issue = 5|page = 827–831|doi = 10.1021/jf60195a002}}</ref> |
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The term cyclopentenone may also refer to a ] wherein the cyclopentenone ] is a subsection of a larger molecule. In this regard, cyclopentenones are found in a large number of ]s, including ], the ]s, and several ]s. |
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The term cyclopentenone may also refer to a ] wherein the cyclopentenone ] is a subunit of a larger molecule. Cyclopentenones are found in a large number of ]s, including ], the ]s, and several ]s.<ref>{{Cite journal |last1=Simeonov |first1=Svilen P. |last2=Nunes |first2=João P. M. |last3=Guerra |first3=Krassimira |last4=Kurteva |first4=Vanya B. |last5=Afonso |first5=Carlos A. M. |date=2016-05-25 |title=Synthesis of Chiral Cyclopentenones |url=https://pubs.acs.org/doi/10.1021/cr500504w |journal=Chemical Reviews |language=en |volume=116 |issue=10 |pages=5744–5893 |doi=10.1021/cr500504w |pmid=27101336 |issn=0009-2665}}</ref> |
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==Synthesis== |
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==Synthesis== |
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Cyclopentenones can be synthesized in a number of ways. Industrially, the most common procedures are elimination of α-]-] using ]<ref name="prep1">{{Citation| inventor-last = Daisuke| inventor-first = Fukushima | inventor2-last = Norihiko| inventor2-first = Hirata| publication-date = 2004-05-12|title = Process for producing 2-bromocyclopentanone | country-code = US| patent-number =EP1418166}}</ref> and ]-]-] cascades of unsaturated ]s as shown below.<ref name="prep2">{{Citation| inventor-last = Liang|inventor-first= Shelue|inventor2-last= Haunert|inventor2-first= Andrea|inventor3-last= Huber-Dirr|inventor3-first= Sylvia |inventor4-last= Fischer|inventor4-first= Rolf-Hartmuth|publication-date = 2004-11-25|title = Process for preparing cyclopentenone | country-code = US| patent-number =EP1422212}}</ref> |
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2-Cyclopentenones can be synthesized in a number of ways. One of the routes involves elimination of α-]-] using ]<ref name="prep1">{{cite patent| inventor-last = Daisuke| inventor-first = Fukushima | inventor2-last = Norihiko| inventor2-first = Hirata| publication-date = 2004-05-12|title = Process for producing 2-bromocyclopentanone | country-code = US| patent-number =EP1418166}}</ref> and ]-]-] cascades of unsaturated ]s as shown below.<ref name="prep2">{{cite patent| inventor-last = Liang|inventor-first= Shelue|inventor2-last= Haunert|inventor2-first= Andrea|inventor3-last= Huber-Dirr|inventor3-first= Sylvia |inventor4-last= Fischer|inventor4-first= Rolf-Hartmuth|publication-date = 2004-11-25|title = Process for preparing cyclopentenone | country-code = US| patent-number =EP1422212}}</ref> |
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The acid-catalyzed dehydration of cyclopentanediols affords cyclopentenone.<ref>{{cite journal|title=2-Cyclopentenone |author=Charles H. DePuy |author2=K. L. Eilers|journal=Org. Synth.|year=1962|volume=42|page=38|doi=10.15227/orgsyn.042.0038}}</ref> |
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As a functional group, the synthesis of cyclopentenones is accomplished in a variety of other ways, including the ] from divinyl ketones, ] from ]s, ] from the corresponding ]s, ] of the corresponding cyclic ]s, and the ] from ]s, ]s, and ].<ref name="prep3">"Cyclopentenone synthesis"</ref> |
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As a functional group, the synthesis of 2-cyclopentenones is accomplished in a variety of other ways, including the ] from ]s, ] from ]s, ] from the corresponding ]s, ] of the corresponding cyclic ]s, and the ] from ]s, ]s, and ].<ref name="prep3">{{cite web|last1=Müller|first1=Reto|title=Synthesis of cyclopentenones|url=https://www.organic-chemistry.org/synthesis/C1C/cyclic/enones/cyclopentenones.shtm|website=Organic Chemistry Portal|access-date=3 March 2015}}</ref> |
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==Reactions== |
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==Reactions== |
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As an ], 2-cyclopentenone undergoes the typical reactions of α-β unsaturated ketones, including ], the ], and the ]. Cyclopentenone also functions as an excellent ] in the ], reacting with a wide variety of ]s. In one example, a ] is reacted with a cyclopentenone to yield a fused tricyclic system en route to the synthesis of coriolin.<ref name="react">{{cite journal|last1=Danishefsky|first1=Samuel|last2=Zamboni|first2=Robert|last3=Kahn|first3=Michael|last4=Etheredge|first4=Sarah Jane|title=Total synthesis of dl-coriolin|journal=Journal of the American Chemical Society|date=March 1980|volume=102|issue=6|pages=2097–2098|doi=10.1021/ja00526a061}}</ref> |
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As an ], cyclopentenone undergoes the typical reactions of α-β unsaturated ketones, including ], the ], and the ]. Cyclopentenone also functions as an excellent ] in the ], reacting with a wide variety of ]s. In one example, a ] is reacted with a cyclopentenone to yield a fused tricyclic system en route to the synthesis of coriolin.<ref name="react">{{cite|author = Danishefsky, S.; Zamboni, R.; Kahn, M.; Etheredge, S.J.|journal = ]|year = 1980|volume = 102|issue = 6|page = 2097–2098|doi = 10.1021/ja00526a061}}</ref> |
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==Occurrence== |
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It has been isolated from pressure-cooked pork ] by simultaneous steam ] and continuous ].<ref name=isol>{{cite journal|last1=Mussinan|first1=Cynthia J.|last2=Walradt|first2=John P.|title=Volatile constituents of pressure cooked pork liver|journal=Journal of Agricultural and Food Chemistry|date=May 1974|volume=22|issue=5|pages=827–831|doi=10.1021/jf60195a002}}</ref><ref>{{cite journal |doi=10.1021/cr500504w|title=Synthesis of Chiral Cyclopentenones|year=2016|last1=Simeonov|first1=Svilen P.|last2=Nunes|first2=João P. M.|last3=Guerra|first3=Krassimira|last4=Kurteva|first4=Vanya B.|last5=Afonso|first5=Carlos A. M.|journal=Chemical Reviews|volume=116|issue=10|pages=5744–5893|pmid=27101336}}</ref> |
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==Related compounds== |
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*] |
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*cyclobutenone<ref>{{cite journal |doi=10.15227/orgsyn.089.0491 |title=Preparation of Cyclobutenone |journal=Organic Syntheses |date=2012 |volume=89 |page=491|author=A. G. Ross, X. Li, S. J. Danishefsky |
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|doi-access=free }}</ref> |
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*] |
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*cycloheptenone<ref>{{cite journal |doi=10.15227/orgsyn.059.0113 |title=One-Carbon Ring Expansion of Cycloalkanones to Conjugated Cycloalkenones: 2-Cyclohepten-1-One |journal=Organic Syntheses |date=1979 |volume=59 |page=113|author=Y. Ito, S. Fujii, M. Nakatuska, F. Kawamoto,T. Saegusa }}</ref> |
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==References== |
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==References== |
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