5448-22-6

Usage

Uses

Used in Organic Synthesis:
Trans-2-tert-butylcyclohexan-1-ol is utilized as a chiral building block in organic synthesis for its unique structural properties that facilitate the creation of complex organic molecules.
Used in Fragrance and Flavor Industry:
In the fragrance and flavor industry, trans-2-tert-butylcyclohexan-1-ol is employed as a component to add specific scents or tastes to products, capitalizing on its ability to contribute distinct olfactory or gustatory characteristics.
Used in Pharmaceutical Industry:
Trans-2-tert-butylcyclohexan-1-ol is also used in the pharmaceutical industry, where it serves as a key intermediate in the synthesis of various medicinal compounds, leveraging its chemical properties to enhance drug development and formulation.

InChI:InChI=1S/C10H20O/c1-10(2,3)8-6-4-5-7-9(8)11/h8-9,11H,4-7H2,1-3H3/t8-,9-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 1728-46-7 2-tert-butylcyclohexanone 
• 88-18-6 2-tert-Butylphenol 
• 3419-66-7 1-tert-butyl-1-cyclohexene 
• 108-94-1 cyclohexanone 
• 286-20-4 cyclohexane-1,2-epoxide 
• 7214-18-8 cis-2-tert-butylcyclohexanol 

Downstream Products

• 88-41-5 trans-2-tert-butylcyclohexyl acetate 
• 7214-18-8 cis-2-tert-butylcyclohexanol 
• 3763-51-7 2-t-butylcyclohexanone 
• 14132-21-9 (-)-2-tert-butylcyclohexanone 
• 13492-07-4 (+)-(1S,2R)-2-(tert-butyl)cyclohexanol 
• 98104-30-4 trans 2-tert-butylcyclohexanol 
• 557088-93-4 (+)-3β-Acetoxy-Δ⁵-aetiensaeure-trans-2-tert.-butyl-cyclohexanolester 
• 137943-97-6 (3aS,7aS)-2-((1S,2R)-2-tert-Butyl-cyclohexyloxy)-1,3-dimethyl-octahydro-benzo[1,3,2]diazaphosphole 

Relevant academic research and scientific papers

The temperature dependence of the diastereoselective reduction of 2-t-butylcyclohexanone with diisobutyl-aluminium-2,6-di-t-butyl-4-methylphenoxide

The diastereoselectivity of the reduction of 2-t-butylcyclohexanone (1) with diisobutylaluminium-2,6-di-t-butyl-4-methylphenoxide (2) is investigated as a function of the temperature and the conversion. The relevant selection steps are characterized on the basis of the isoinversion principle. The kinetically controlled formation of the alcoholate intermediates as well as the thermodynamically controlled Meerwein-Ponndorf-Verley type equilibration are recognized as the two selection steps of the reduction.

Cobalt-Nanoparticles Catalyzed Efficient and Selective Hydrogenation of Aromatic Hydrocarbons

The development of inexpensive and practical catalysts for arene hydrogenations is key for future valorizations of this general feedstock. Here, we report the development of cobalt nanoparticles supported on silica as selective and general catalysts for such reactions. The specific nanoparticles were prepared by assembling cobalt-pyromellitic acid-piperazine coordination polymer on commercial silica and subsequent pyrolysis. Applying the optimal nanocatalyst, industrial bulk, substituted, and functionalized arenes as well as polycyclic aromatic hydrocarbons are selectively hydrogenated to obtain cyclohexane-based compounds under industrially viable and scalable conditions. The applicability of this hydrogenation methodology is presented for the storage of H2 in liquid organic hydrogen carriers.

Enantioselective Hydroazidation of Trisubstituted Non-Activated Alkenes

A one-pot procedure for the enantioselective hydroazidation of non-activated trisubstituted alkenes is described. Hydroboration with monoisopinocampheylborane (IpcBH2) provides dialkylboranes that are in situ selectively converted into monoalkyl-substituted catecholboranes; these undergo radical azidation upon treatment with benzenesulfonyl azide and a radical initiator. Enantiomerically enriched azides were thus obtained in yields of 59–81 % and enantioselectivities of up to 94:6 e.r. (98:2 e.r. if the intermediate dialkylborane is purified by crystallization). A rapid access to enantiomerically pure (+)-rodocaine is also described. The use of other arenesulfonyl radical traps enables enantioselective hydroallylation, hydrosulfanylation, and hydrobromination reactions with yields of 71–86 %.

Selective reduction of organic compounds with Al- trifluoromethanesulfonyldiisobutylalane. Comparison of its reactivity with Al-methanesulfonyldiisobutylalane

The new MPV type reagent, Al-trifluoromethanesulfonyldiisobutylalane (DIBAO3SCF3), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined, and compared its reactivity with that of Al-methanesulfonyldiisobutylalane (DIBAO3SCH 3) in order to understand the fluorine-substituent effect on its reactivity. In general, the reactivity of DIBAO3SCF3 appears to be much higher than that of DIBAO3SCH3, apparently due to the acidity increase by the electron-withdrawing fluorine-substituent. The reagent reduced aldehydes and ketones readily, but showed a perfect selectivity in the reduction of α,β-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in an absolutely 100% purity. In addition, the reagent achieved the regioselective cleavage of phenyl-or/and alkyl-substituted epoxides to the less substituted alcohols in a perfect regioselectivity. Moreover, the reagent also showed an high stereoselectivity in the reduction of substituted cycloalkanones to produce the thermodynamically more stable alcohol epimers exclusively.

Selective reduction of organic compounds with Al- methanesulfonyldiisobutylalane

The new MPV type reagent, Al-methanesulfonyldiisobutylalane (DIBAO 3SCH3), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined in order to find out a new reducing system with high selectivity in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones and epoxides. The reagent exhibits a unique reducing applicability in organic synthesis. Thus, the reagent can achieve a clean 1,2-reduction of α,β-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in 100% purity. In addition, the reagent shows an excellent regioselectivity in the ring-opening reaction of epoxides. Finally, DIBAO3SCH3 shows a high stereo-selectivity in the reduction of cyclic ketones to produce the thermodynamically more stable epimers exclusively.

Copper-catalyzed hydrosilylation with a bowl-shaped phosphane ligand: Preferential reduction of a bulky ketone in the presence of an aldehyde

Chemical Equation Presented Hollywood bowl: A highly active copper catalyst with a bowl-shaped phosphane (bsp) ligand was used in the hydrosilylation reaction of bulky ketones. The preferential reduction of a bulky ketone in the presence of an unprotected aldehyde is unprecedented.

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H 2 pressures (10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellet yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.

Raney Ni-Al alloy-mediated reduction of alkylated phenols in water

Raney Ni-Al alloy in a dilute aqueous alkaline solution has been shown to be a very powerful reducing agent in the hydrogenation of phenol and alkylated phenols to the corresponding cyclohexanol derivatives.

Stereoselective hydrogenation of tert-butylphenols over charcoal-supported rhodium catalyst in supercritical carbon dioxide solvent

Hydrogenation of 2-, 3-, and 4-tert-butylphenols was studied over a charcoal-supported rhodium catalyst in supercritical carbon dioxide (scCO2) solvent, and the results were compared with those in organic solvents. In the hydrogenation of 4-ter

Al-isopropoxydiisobutylalane: A study of the effect of solvent on the rate and stereoselectivity of cyclic ketone reduction

The effect of solvent on the rate and stereoselectivity of cyclic ketone reduction by Al-isopropoxydiisobutylalane (DIBAiOPr) has been investigated. In dichloromethane, DIBAiOPr behaves as a bulky reducing agent, approaching the carbonyl group along an equatorial trajectory to produce the axial alcohol with > 10:1 stereoselectivity. In sharp contrast, reduction in toluene gives the complementary outcome, affording the thermodynamically more stable isomer with > 99:1 stereoselectivity.