Adamantanone

Adamantanone is the ketone of adamantane. A white solid, it is prepared by oxidation of adamantane.^[1] It is a precursor to several adamantane derivatives.^[2]

Adamantanone

Names
Preferred IUPAC name Adamantan-2-one
Other names Tricyclo[3.3.1.13,7]decanone 2-Adamantanone
Identifiers
CAS Number	700-58-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:40611
ChEMBL	ChEMBL2041316
ChemSpider	57725
DrugBank	DB02125
ECHA InfoCard	100.010.772
EC Number	211-847-2
Gmelin Reference	122962
PubChem CID	64151
UNII	UI7W503L08
CompTox Dashboard (EPA)	DTXSID9022108
InChI InChI=1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2 Key: IYKFYARMMIESOX-UHFFFAOYSA-N
SMILES C1C2CC3CC1CC(C2)C3=O
Properties
Chemical formula	C10H14O
Molar mass	150.221 g·mol−1
Appearance	white solid
Melting point	270 °C (518 °F; 543 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H318, H410
Precautionary statements	P264, P270, P273, P280, P301+P310, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Adamantanone and some related polycyclic ketones, are reluctant to form enolates. This barrier arises because the resulting carbanion cannot exist in conjugation with the carbonyl pi-bond.^[3][4][5]