5-Hydroxyadamantan-2-one

Description

5-Hydroxy-2-adamantanone (5-hydroxyadamantan-2-one) is a versatile starting material for synthesising various 2,5- or 1,4-disubstituted adamantanes. Chemical methods for synthesizing 5-hydroxy-2-adamantanone include disproportionation of 2-hydroxyadamantane and oxidation of 2-adamantanone. A synthetic approach to produce 5-hydroxy-2-adamantanone using P450cam (CYP101A1; a camphor monooxygenase) coupled with NADH regeneration as an oxidation biocatalyst has been reported[1].

Chemical properties

White crystal or crystalline powder

The Uses of 5-Hydroxyadamantan-2-one

anthelmintic

The Uses of 5-Hydroxyadamantan-2-one

5-Hydroxy-2-adamantanone may be used in the following studies:

• As a model compound to investigate the application of lanthanide NMR shift reagents for the analysis of disubstituted derivative of adamantane.
• As a starting material for the synthesis of E-2-amino-5-hydroxyadamantane.
• As a starting material for the synthesis of 4-(triphenylsilyloxy)adamantan-1-ol.

Definition

ChEBI: Idramantone is a member of adamantanones.

brand name

INDICLOR (Nycomed Amersham).

General Description

5-Hydroxy-2-adamantanone is a disubstituted derivative of adamantane. The biocatalyzed synthesis of 5-hydroxy-2-adamantanone from 2-adamantanone has been investigated.

References

[1] Toshiki Furuya . “Biocatalytic production of 5-hydroxy-2-adamantanone by P450cam coupled with NADH regeneration.” Journal of Molecular Catalysis B-enzymatic 94 (2013): Pages 111-118.