28664-08-6

Usage

Uses

Used in Fragrance Industry:
6,6-Dimethylbicyclo[3.1.1]heptan-2-ol is used as a fragrance ingredient for its distinctive scent. It is incorporated into various consumer products such as perfumes, soaps, and detergents to provide a pleasant and long-lasting aroma.
Used in Pharmaceutical Synthesis:
6,6-Dimethylbicyclo[3.1.1]heptan-2-ol is used as a key intermediate in the synthesis of pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Synthesis:
6,6-Dimethylbicyclo[3.1.1]heptan-2-ol is also used in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products that can improve crop yield and protect plants from pests and diseases.
Used in Chemical Research:
Due to its unique structure and properties, 6,6-dimethylbicyclo[3.1.1]heptan-2-ol is an interesting target for synthetic chemistry and chemical research. It can be used to explore new synthetic pathways, develop novel compounds, and gain insights into the fundamental aspects of chemical reactions and processes.

InChI:InChI=1/C9H16O/c1-9(2)6-3-4-8(10)7(9)5-6/h6-8,10H,3-5H2,1-2H3

Upstream product

• 24903-95-5 nopinone 
• 60-29-7 diethyl ether 
• 103533-23-9 trans-peroxymyrtanic acid 
• 51703-63-0 6,6-dimethylbicyclo<3.1.1>heptan-2β-ol 
• 24903-95-5 6,6-dimethylbicyclo[3.1.1]heptan-2-one 

Downstream Products

• 32863-61-9 apopinene 
• 111821-63-7 7,7-dimethylbicyclo<2.2.1>heptan-endo-2-ol 

Relevant academic research and scientific papers

Water-resistant solid Lewis acid catalysts: Meerwein-Ponndorf-Verley and Oppenauer reactions catalyzed by tin-beta zeolite

The catalytic activity of Sn-beta zeolite in the Meerwein-Pondorf-Verley reduction of carbonyl compounds with secondary alcohols as reductants and Oppenauer oxidation of alcohols were performed with quantitative yields to the corresponding product. The catalyst had an excellent activity and selectivity even after four catalytic recycles, and good stereoselectivities to the thermodynamic less favorable cis-alcohol isomer when alkyl-cyclohexanones were used as substrates. A prochiral ketone was reduced within an enantiomeric excess close to 50% when using a chiral alcohol as the reducing reactant. IR studies using cyclohexanone as probe molecule over beta zeolites showed that the more specific Lewis acid sites in the framework of Sn-beta were responsible for its better catalytic activity with respect to Ti- or Al-beta. The order of hydrophobicity of the samples was Ti-beta > Sn-beta > Al-beta. Ti-beta and Sn-beta retained a higher percentage of catalytic activity when water was present in the reaction media. Even with ～ 4 wt % of H2O (0.2 g) in the media, Sn-beta yielded a higher turnover number than Ti- or Al-beta when working in the absence of water.

Acceleration of the reduction of aldehydes and ketones using Mn(dpm)3 catalyst and phenylsilane in the presence of dioxygen

Saturated ketones and aldehydes are reduced to alcohols by phenylsilane and Mn(dpm)3(cat) in the presence of dioxygen.

Ion-molecule complexes in 1,2 alkyl shifts

The internal return of neutral leaving groups was studied in rearrangements of polycyclic systems (2-norpinyl → 2-norbornyl, endo- → exo-tricyclo[5.2.1.02.6]dec-8-yl, bicyclo[3.2.0]hept-2-yl → 7-norbornyl, and 4-protoadamantyl → 2-adamantyl). Acid catalysis was applied to 18O-labeled alcohols in aqueous organic solvents, to alcohols in methanol, and to ethers R-O-R′ in alcohols R″-OH. The leaving group was found to attack the migration origin in competition with solvent molecules. Return:exchange ratios were obtained from product distributions, either directly or by kinetic simulation (in cases of partial exchange prior to rearrangement). If departure and return of the leaving group occur on the same side of the carbon framework, return:exchange ratios ranging from 1 to 11.5 were observed. Less internal return was found for bridged than for open carbocations. Migration of the departing molecule to the opposite face (exo ? endo) or to a β carbon is a minor process (return:exchange ～ 0.1), in accordance with previous reports on inverting displacements and allylic 1,3 shifts. These data are rationalized in terms of short-lived ion-molecule (ion-dipole) complexes whose collapse competes with ligand exchange.

Trapping of the 6,6-Dimethylbicyclohept-2-yl Free Radical by SH2 Reaction upon Peracid

The free radical 6,6-dimethylbicyclohept-2-yl (7) has been obtained by decarboxylation of cis- or trans-6,6-dimethylbicycloheptane-2-peroxycarboxylic acids (6a and 6b). 7 trapped by reaction with the initial peracid gave a stereochemical mixture of α- and β-nopinol (8a and 8b).The ratio 8b/8a is around 12, independent of the initial peracid 6a or 6b and its initial concentrations.This value is mainly due to the steric effect of one of the methyl groups branched on C7 in 7.The structure of 7 is discussed.By a competitive reaction 7 undergoes ring opening to afford 2-(3-cyclohexenyl)-2-propyl free radical (9) which by reaction upon peracid leads to 2-(3-cyclohexenyl)-2-propanol (10). 7 was successfully trapped because its reaction with peracid is rapid enough.The ratio of the two alcohols 8/10 leads to an estimation of 1*106 M-1 s-1 for the rate constant of the reaction of 7 with peracids