24669-56-5

Usage

Uses

Used in Fragrance Industry:
Tricyclo[4.3.1.13,8]undecan-4-one is used as a fragrance ingredient for its distinctive scent, adding value to cosmetic and personal care products by enhancing their olfactory appeal.
Used in Medicinal Chemistry:
Tricyclo[4.3.1.13,8]undecan-4-one is used as a versatile building block in organic synthesis for its potential biological activities, including antimicrobial and anti-inflammatory properties, contributing to the development of new pharmaceutical compounds.
Used in Materials Science:
Tricyclo[4.3.1.13,8]undecan-4-one is utilized in materials science for its rigid and stable configuration, which can be exploited in the design and synthesis of novel materials with specific properties.
Further research is needed to fully understand the potential applications and effects of tricyclo[4.3.1.13,8]undecan-4-one in these industries and explore its full potential in various fields.

InChI:InChI=1/C11H16O/c12-11-6-9-2-7-1-8(3-9)5-10(11)4-7/h7-10H,1-6H2

Upstream product

• 875-72-9 2-methylideneadamantane 
• 55638-01-2 2,4-Dehydro-5-homoadamantanon 
• 25763-45-5 homoadamantan-4-ol 
• 97382-23-5 3,4-dihydroxytricyclo<4.3.1.1^3,8>undecane 
• 174906-23-1 5-trifluoroacetyltricyclo<4.3.1.1^3,8>undecan-4-one 
• 281-46-9 homoadamantane 
• 700-58-3 2-Adamantanone 
• 80-11-5 N-nitroso-p-toluenesulfonamide 
• 28529-71-7 (1r,3r,5r,7r)‐2‐(aminomethyl)adamantan‐2‐ol 
• 186581-53-3 diazomethane 

Downstream Products

• 162463-58-3 3-benzoyl-5-hydroxy-5-trifluoromethyl-3,4-diazatetracyclo<7.3.1.1^7,11.0^2,6>tetradeca-2(6)-ene 
• 14504-80-4 3-homoadamantanol 
• 21898-95-3 1-methoxyhomoadamantane 
• 133189-64-7 4-(4-Methoxyphenyl)-4-homoadamanten-3-yl acetate 
• 133189-57-8 3,4-Dihydroxy-4-(4-methoxyphenyl)tricyclo<4.3.1.1^3,8>undecane 
• 133189-65-8 4-Phenyl-4-homoadamanten-3-yl acetate 
• 133189-62-5 3-(4-Methoxyphenyl)tricyclo<4.3.1.1^3,8>undecan-4-one 
• 133189-58-9 3,4-Dihydroxy-4-phenyltricyclo<4.3.1.1^3,8>undecane 
• 133189-63-6 3-Phenyltricyclo<4.3.1.1^3,8>undecan-4-one 
• 1660-04-4 1-acetyladamantane 
• 1660-05-5 1-(adamantan-1-yl)propan-1-one 
• 25763-46-6 4-Homoadamantyl tosylate 

Relevant academic research and scientific papers

Heterocyclization of 5-trifluoroacetyltricyclo-[4.3.1.13,8]undecan-4-one to some 6- and 7-membered nitrogen heterocycles

Heterocyclization study of 5-trifluoroacetyl[4.3.1.13,8]undecan-4-one into pyrimidine, pyridine, and 1,4-diazepine derivatives as a route to trifluoromethylated homoadamantanefused 6- and 7-membered nitrogen heterocyctes is reported.

Convenient Synthesis of Ethyl 5-Oxohomoadamantane-4-carboxylate: A Useful Precursor of Polyfunctional Homoadamantanes

A facile and convenient synthesis of ethyl 5-oxohomoadamantane-4-carboxylate is reported, and its chemical properties as a cage analogue of acetoacetic ester are investigated. Various derivatives of homoadamantane were synthesized through the reaction of 5-oxohomoadamantane-4-carboxylate with electrophilic agents, binucleophiles, and hydrazoic acid. Some new unusual products were obtained by the reaction of that β-keto ester with nitric acid and nitrosyl chloride. Cage compounds synthesized could be used as precursors for the diverse condensed heterocyclic compounds with potential viral ion channel abrogating activity that possess conformationally rigid lipophilic moieties.

New methylene homologation method for cyclic ketones

Teaching new tricks to an old dog: By intercepting adducts between ketones and lithium trimethylsilyldiazomethane, a new Tiffeneau-Demjanov type methylene homologation could be realized in a single-step operation. Among proton sources and Lewis acids, silica gel was found to be the most effective reagent for the protonation of intermediates and their subsequent ring expansion (see scheme). Copyright

METHODS OF USE OF ANTIVIRAL COMPOUNDS

The present invention relates, in part, to methods of treatment, prevention, and inhibition of viral disorders. In one aspect, the present invention relates to inhibition of the M2 proton channel of influenza viruses (e.g. influenza A virus) and other similar viroporins (e.g., VP24 of Ebola and Marburg viruses; and NS3 protein of Bluetongue). The present invention further relates, inter alia, to compounds which have been shown to possess antiviral activity, in particular, inhibiting the M2 proton channel of influenza viruses.

Adamantanethione and diazomethane; dual regiochemistry of cycloadditions [1]

Cydoaddilions of diazoalkanes to thiones take place in two directions furnishing 1,3,4-thiadiazolines and/or their 1,2,3-isomers, depending upon the substituents. Adamantanethione and diazomethane give rise to hoth regioisomers; a literature report on the high solvent dependence of the isomer ratio is confirmed, and the two regioisomers are isolated. The 1,3,4-thiadiazoline 20 eliminates N2 at 80°C (t1/2 55 s) in a 1,3-dipolar cycdoreversion: the thiocarbonyl ylide 22 generated undergoes electrocyclization, forming a thiirane, or is intercepted by reactions with HX (thiols, alcohols) or dipolarophilic multiple bonds. The N2 extrusion from the isomeric 1,2,3-thiadiazoline 21 is at 80°C 600 times slower: the formation of the spirothiirane and homoadamantane-2-thione is explained by a diazonium thiolate as an intermediate.

A new route to 3-labeled or 3-substituted 4-homoadamantanones

The pinacol rearrangement of 3,4-dihydroxyhomoadamantanes containing carbon-13, deuterium, and alkyl, or an aryl subsituent at the C-4 position provides a new route to the title compounds.

Competitive and Regiospecific Bridgehead Substitution in Electrophilic Oxidation Reactions of Homoadamantane

Oxidation of homoadamantane with chromic acid, lead tetraacetate, p-nitroperbenzoic acid, or bromine occurs by competitive attack at the C-3 (major) and C-1 (minor) bridgehead positions.In striking contrast, dry ozonation of homoadamantane adsorbed on silica gel leads to regiospecific substitution at the chemically equivalent C-3 and C-6 bridgehead positions.A consequence of this observation is that some 1,3- and 3,6-disubstituted homoadamantanes can be prepared by dry ozonation of suitably substituted homoadamantane derivatives.

STREIC EFFECTS ON REACTION RATES II: RATE AND EQUILIBRIUM CONSTANTS FOR OXIDATION OF BICYCLIC ALCOHOLS

Equilibrium constants for oxidation of a series of bicyclic alcohols with cyclohexanone have been determined under Meerwein-Pondorf conditions.The data provide the thermodynamic background for interpretation of the mechanism of alcohol oxidation and ketone reductions.Free energies of the equilibrium (ΔGox) are compared with values calculated by molecular mechanics.