Cyclohexenone

Cyclohexenone[1]
IUPAC name 1-Cyclohex-2-enone
Identifiers
CAS number	930-68-7 Y
PubChem	13594
ChemSpider	13005 Y
KEGG	C02395 Y
ChEBI	CHEBI:15977 Y
Jmol-3D images	Image 1
SMILES C1CC=CC(=O)C1
InChI InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2 Y Key: FWFSEYBSWVRWGL-UHFFFAOYSA-N Y InChI=1/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2 Key: FWFSEYBSWVRWGL-UHFFFAOYAT
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
Hazards
NFPA 704	3 1 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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.

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

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)