Surf Wiki
Save to docs
general/enones

From Surf Wiki (app.surf) — the open knowledge base

Cyclopentenone

Cyclopentenone

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

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

Occurrence

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

References

References

  1. (2016-05-25). "Synthesis of Chiral Cyclopentenones". Chemical Reviews.
  2. "Process for producing 2-bromocyclopentanone".
  3. "Process for preparing cyclopentenone".
  4. Charles H. DePuy. (1962). "2-Cyclopentenone". Org. Synth..
  5. "Synthesis of cyclopentenones".
  6. (March 1980). "Total synthesis of dl-coriolin". Journal of the American Chemical Society.
  7. (May 1974). "Volatile constituents of pressure cooked pork liver". Journal of Agricultural and Food Chemistry.
  8. 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.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

enones cyclopentenes
Want to explore this topic further?

Ask Mako anything about Cyclopentenone — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report