Misplaced Pages

Cyclopentenone: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
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 Latest revision as of 17:43, 11 September 2024 edit undoBernanke's Crossbow (talk | contribs)Extended confirmed users7,860 edits →Synthesis: link 
(35 intermediate revisions by 25 users not shown)
Line 1: Line 1:
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 426291372 | verifiedrevid = 460110678
|ImageFileL1=Cyclopentenone.png | ImageFileL1 =Cyclopentenone.png
|ImageSizeL1=80px | ImageSizeL1 =80px
|ImageFileR1=Cyclopentenone3d.png | ImageFileR1 =Cyclopentenone3d.png
|ImageSizeR1=110px | ImageSizeR1 =110px
|IUPACName= 2-Cyclopenten-1-one
| PIN = Cyclopent-2-en-1-one
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12999 | ChemSpiderID = 12999
| SMILES = C1CC(=O)C=C1 | SMILES = C1CC(=O)C=C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2 | StdInChI =1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BZKFMUIJRXWWQK-UHFFFAOYSA-N | StdInChIKey = BZKFMUIJRXWWQK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=930-30-3
| ChEMBL = 52190 | CASNo =930-30-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=13588
| UNII = Q0U2IGF9CK
| ChEBI = 141550
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 52190
⚫ | PubChem =13588
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=5 | H=6 | O=1
| Formula=C<sub>5</sub>H<sub>6</sub>O
| MolarMass=82.04&nbsp;g&middot;mol<sup>&minus;1</sup> | Density = 0.98&nbsp;g&middot;mL<sup>&minus;1</sup>
| BoilingPtC = 150
| Density = 0.98&nbsp;g&middot;mL<sup>&minus;1</sup>
⚫ | Solubility = almost insoluble in ] }}
| BoilingPt = 150&nbsp;&deg;C
⚫ |Section3={{Chembox Hazards
⚫ | Solubility = almost insoluble in ] }}
| MainHazards = Harmful
⚫ | Section3 = {{Chembox Hazards
| MainHazards = Harmful | FlashPtC = 42
| FlashPt = 42&nbsp;&deg;C
}} }}
}} }}


'''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.
'''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&nbsp;&deg;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&ndash;831|doi = 10.1021/jf60195a002}}</ref>


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. 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>


==Synthesis== ==Synthesis==
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> 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>


] ]


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>
⚫ 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>

⚫ 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>


==Reactions== ==Reactions==
⚫ 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>

⚫ 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&ndash;2098|doi = 10.1021/ja00526a061}}</ref>


] ]

==Occurrence==
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>

==Related compounds==
*]
*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
|doi-access=free }}</ref>
*]
*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>


==References== ==References==
{{reflist}} {{reflist}}
⚫ ]


⚫ ]
]
]

Latest revision as of 17:43, 11 September 2024

Cyclopentenone
Names
Preferred IUPAC name Cyclopent-2-en-1-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.012 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2Key: BZKFMUIJRXWWQK-UHFFFAOYSA-N
SMILES
  • C1CC(=O)C=C1
Properties
Chemical formula C5H6O
Molar mass 82.102 g·mol
Density 0.98 g·mL
Boiling point 150 °C (302 °F; 423 K)
Solubility in water almost insoluble in water
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Harmful
Flash point 42 °C (108 °F; 315 K)
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

2-Cyclopentenone is the organic compound with the chemical formula (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.

The term cyclopentenone may also refer to a structural motif wherein the cyclopentenone moiety is a subunit of a larger molecule. Cyclopentenones are found in a large number of natural products, including jasmone, the aflatoxins, and several prostaglandins.

Synthesis

2-Cyclopentenones can be synthesized in a number of ways. One of the routes involves elimination of α-bromo-cyclopentanone using lithium carbonate and Claisen condensation-decarboxylation-isomerization cascades of unsaturated diesters as shown below.

Industrial synthesis of cyclopentenone
Industrial synthesis of cyclopentenone

The acid-catalyzed dehydration of cyclopentanediols affords cyclopentenone.

As a functional group, the synthesis of 2-cyclopentenones is accomplished in a variety of other ways, including the Nazarov cyclization reaction from divinyl ketones, Saegusa–Ito oxidation from cyclopentanones, ring-closing metathesis from the corresponding dienes, oxidation of the corresponding cyclic allylic alcohols, and the Pauson–Khand reaction from alkenes, alkynes, and carbon monoxide.

Reactions

As an enone, 2-cyclopentenone undergoes the typical reactions of α-β unsaturated ketones, including nucleophilic conjugate addition, the Baylis–Hillman reaction, and the Michael reaction. Cyclopentenone also functions as an excellent dienophile in the Diels–Alder reaction, reacting with a wide variety of dienes. In one example, a Danishefsky-type diene is reacted with a cyclopentenone to yield a fused tricyclic system en route to the synthesis of coriolin.

Cyclopentenone in the synthesis of coriolin
Cyclopentenone in the synthesis of coriolin

Occurrence

It has been isolated from pressure-cooked pork liver by simultaneous steam distillation and continuous solvent extraction.

Related compounds

References

  1. Simeonov, Svilen P.; Nunes, João P. M.; Guerra, Krassimira; Kurteva, Vanya B.; Afonso, Carlos A. M. (2016-05-25). "Synthesis of Chiral Cyclopentenones". Chemical Reviews. 116 (10): 5744–5893. doi:10.1021/cr500504w. ISSN 0009-2665. PMID 27101336.
  2. US EP1418166, Daisuke, Fukushima & Norihiko, Hirata, "Process for producing 2-bromocyclopentanone", published 2004-05-12 
  3. US EP1422212, Liang, Shelue; Haunert, Andrea & Huber-Dirr, Sylvia et al., "Process for preparing cyclopentenone", published 2004-11-25 
  4. Charles H. DePuy; K. L. Eilers (1962). "2-Cyclopentenone". Org. Synth. 42: 38. doi:10.15227/orgsyn.042.0038.
  5. Müller, Reto. "Synthesis of cyclopentenones". Organic Chemistry Portal. Retrieved 3 March 2015.
  6. Danishefsky, Samuel; Zamboni, Robert; Kahn, Michael; Etheredge, Sarah Jane (March 1980). "Total synthesis of dl-coriolin". Journal of the American Chemical Society. 102 (6): 2097–2098. doi:10.1021/ja00526a061.
  7. Mussinan, Cynthia J.; Walradt, John P. (May 1974). "Volatile constituents of pressure cooked pork liver". Journal of Agricultural and Food Chemistry. 22 (5): 827–831. doi:10.1021/jf60195a002.
  8. Simeonov, Svilen P.; Nunes, João P. M.; Guerra, Krassimira; Kurteva, Vanya B.; Afonso, Carlos A. M. (2016). "Synthesis of Chiral Cyclopentenones". Chemical Reviews. 116 (10): 5744–5893. doi:10.1021/cr500504w. PMID 27101336.
  9. A. G. Ross, X. Li, S. J. Danishefsky (2012). "Preparation of Cyclobutenone". Organic Syntheses. 89: 491. doi:10.15227/orgsyn.089.0491.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. Y. Ito, S. Fujii, M. Nakatuska, F. Kawamoto,T. Saegusa (1979). "One-Carbon Ring Expansion of Cycloalkanones to Conjugated Cycloalkenones: 2-Cyclohepten-1-One". Organic Syntheses. 59: 113. doi:10.15227/orgsyn.059.0113.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Categories: