82094-52-8

Usage

Structure

Cyclic diketone with a bulky adamantyl group attached to the butane-1,3-dione backbone

Known as

Adamantylacetone

Potential use

Organic synthesis and as a building block in the development of organic materials and pharmaceuticals

Steric hindrance

Provided by the adamantyl group, useful in controlling the reactivity and selectivity of chemical reactions

Investigated properties

Antimicrobial, antifungal, and anti-inflammatory

Versatility

Potential applications in various fields due to its multiple properties

Upstream product

• 108-24-7 acetic anhydride 
• 1660-04-4 1-acetyladamantane 
• 7732-18-5 water 
• 82094-49-3 {[1-(adamantan-1-yl)ethenyl]oxy}trimethylsilane 
• 75-36-5 acetyl chloride 

Downstream Products

• 1149054-12-5 3-(1-adamantyl)-5-methyl-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Synthesis of difluoroboron adamantyl-containing complexes and pyrazoles based thereon

One-stage synthesis has been developed for the preparation of adamantyl-containing difluoroboron complexes of 1,3-dicarbonyl compounds from 1-(1-adamantyl)ethanone, boron trifluoride etherate, and carboxylic acids anhydrides. The reaction of the complexes with hydrazine hydrate and its derivatives afforded the corresponding adamantyl-containing pyrazoles.

Synthesis of pyrazoles and pyrazolones from 1,3- and 1,4-diketones of the adamantane series

Various pyrazole and dihydropyrazolones containing an adamantane fragment were synthesized from adamantyl-substituted 1,3- and 1,4-diketones, ethyl 4-(1-adamantyl)-2-R-4-oxobutanoates (R = CN, Ac), and ethyl 2-(1-adamantylcarbonyl)-4-oxo-4-phenylbutanoate

Synthesis of Adamantane Derivatives. 59. Reactions of Some Electrophilic Adamantane Derivatives with Unsaturated Organosilanes

1-Adamantyl acetate (5) and 1-adamantyl silyl ether (12) react with unsaturated organosilanes exactly as the chloride 1 does; the reactions of 5 catalyzed by trimethylsilyl triflate and of 12 catalyzed by TiCl4 with 6 and 7 give the corresponding adamantane-substituted products.Under AlCl3-catalyzed conditions, the reactions of 1-adamantylcarbinyl chloride (17) with 6 and 7 give the products which have a homoadamantane skeleton.Interestingly, the reactions of 1-adamantanecarbonyl chloride (22) with α,β- and β,γ-unsaturated silanes proceed smoothly at -78 deg C (TiCl4) or at room temperature (ZnCl2) while the competitive decarbonylation scarcely takes place.Furthermore, the reactions of 22 with silyl enol ethers are efficiently catalyzed with normal Lewis acids such as SnCl4 to give C-adamantanecarbonylated products.Some adamantane-substituted unsaturated silanes are acetylated under the conditions employed for 22 to give structurally related adamantane derivatives.The aldehyde (53) and ketone (54) show different reactivity to the unsaturated organosilanes; the former reacts with 6, 7, and 25 as usual, but the latter does not.