Uses
2-Adamantanone has been used as a probe for the dimensions and characteristics for the substrate binding pocket of alcohol dehydrogenases.
synthesis
Dissolve the alcohol (0.25 mmol) in acetonitrile (3 mL). Add oxidant
1,3-dichloro-5,5-dimethylhydantoin (DCH, 0.148 g, 0.75 mmol) to the
reaction mixture. Add the pre-catalyst MWCNT-{(CH2)3-CO-
NH-TEMPO}n (0.075 g) to the reaction mixture. Sonic the resulting
suspension (1 min.) using an ultrasonic bath. Stir the reaction mixture.
Heat the reaction mixture at 50 °C for 30 minutes. Filter the reaction
mixture. Add CH2Cl2 (10 mL) to the reaction mixture. Wash the organic phase with aqueous Na2S2O3 (10 %, 10 mL) and H2O (10 mL x 2). Dry the residue with Na2SO4. Remove the solvent under reduced pressure using a rotary evaporator to obtain the product.
Chemical Properties
white to off-white crystalline powder with camphor smell, soluble in methanol, ethanol, DMSO and other organic solvents, from synthesis.
Uses
2-Adamantanone was used in the synthesis of dispiro
N-Boc-protected 1,2,4-trioxane and (+/-)-1-(adamantan-2-yl)-2-propanamine.
Definition
ChEBI: Adamantanone is a member of adamantanones.
General Description
2-Adamantanone on deprotonation in the gas phase affords the corresponding β-enolate anion. It reacts with 1,1-dilithio-1-sila-2,3,4,5-tetraphenylsilole to yield 5-silafulvene.
Purification Methods
Purify 2-admantanone by repeated sublimation in vacuo. [Butler et al. J Chem Soc, Faraday Trans II 82 535 1986.]
