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Cyclohexenone

Cyclohexenone^[1]

IUPAC name	1-Cyclohex-2-enone
Identifiers
CAS number	930-68-7
PubChem	13594
SMILES	C1CC=CC(=O)C1
Properties
Molecular 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 noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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.^[2] It is a clear colorless liquid with a boiling point of 171-173 °C.

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Industrially, cyclohexenone is prepared from phenol by Birch reduction.^[3]

Common reactions involving cyclohexenone include nucleophilic conjugate addition with organocopper reagents, Michael reactions and Robinson annulations.^[4]^[5]

References

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