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Cyclohexenone

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Cyclohexenone
Names
IUPAC name 1-Cyclohex-2-enone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.012.021 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2Key: FWFSEYBSWVRWGL-UHFFFAOYSA-N
  • InChI=1/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2Key: FWFSEYBSWVRWGL-UHFFFAOYAT
SMILES
  • C1CC=CC(=O)C1
Properties
Chemical formula C6H8O
Molar mass 96.12712
Appearance Clear colorless liquid
Density 0.993 g/mL
Melting point −53 °C
Boiling point 171-173 °C
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

Cyclohexenone is an organic compound which is a versatile intermediate used in the synthesis of a variety of chemical products such as pharmaceuticals and fragrances. It is a clear colorless liquid with a boiling point of 171-173 °C.

Industrially, cyclohexenone is prepared from phenol by Birch reduction.

Common reactions involving cyclohexenone include nucleophilic conjugate addition with organocopper reagents, Michael reactions and Robinson annulations.

References

  1. Cyclohexenone at Sigma-Aldrich
  2. Podraze, K.F. Org. Prep. Proced. Int., 1991, 23, p. 217.
  3. Organic Building Blocks of the Chemical Industry, Harry H. Szmant, ISBN 978-0471855453
  4. Michael G. Organ and Paul Anderson (1996). "Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent Selectivity". Journal of Chemical Education. 73 (12): 1193. doi:10.1021/ed073p1193.
  5. Tet. Lett. 34, 3881, (1993)
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