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Usage

Uses

Used in Pharmaceutical Industry:
(-)-TRANS-2-TERT-BUTYLCYCLOHEXANOL is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique stereochemistry allows for the creation of enantiomerically pure drugs, which can have different biological activities and reduce potential side effects.
Used in Organic Synthesis:
(-)-TRANS-2-TERT-BUTYLCYCLOHEXANOL is used as a chiral building block in organic synthesis for the preparation of enantiomerically pure compounds. Its distinct three-dimensional arrangement of atoms enables the synthesis of complex molecules with specific stereochemistry, which is crucial for their biological activity and selectivity.
Used in Asymmetric Catalysis:
(-)-TRANS-2-TERT-BUTYLCYCLOHEXANOL can be used as a chiral ligand in asymmetric catalysis. Its unique stereochemical properties allow for the selective formation of enantiomerically pure products, which is essential in the synthesis of biologically active compounds and pharmaceuticals.
Used in Other Industries:
(-)-TRANS-2-TERT-BUTYLCYCLOHEXANOL may also have potential applications in other industries, such as the fragrance and flavor industry, where chiral compounds with specific stereochemistry can impart unique scents or tastes. Additionally, it could be utilized in the development of new materials with specific properties, such as chiral polymers or chiral catalysts for industrial processes.

Upstream product

• 5448-22-6 trans-2-tert-butylcyclohexan-1-ol 
• 14132-21-9 (-)-2-tert-butylcyclohexanone 
• 7150-18-7 3β-acetoxyetienic acid 
• 1228121-67-2 toluene-4-sulfonic acid (1S,2R,3R)-3-tert-butyl-2-hydroxycyclohexyl ester 
• 1728-46-7 2-tert-butylcyclohexanone 
• 142798-18-3 trans-2-tert-Butylcyclohexylchloracetat 
• 88-41-5 trans-2-tert-butylcyclohexyl acetate 

Downstream Products

• 3763-51-7 2-t-butylcyclohexanone 

Relevant academic research and scientific papers

A Practical and Stereoselective In Situ NHC-Cobalt Catalytic System for Hydrogenation of Ketones and Aldehydes

Homogeneous catalytic hydrogenation of carbonyl groups is a synthetically useful and widely applied organic transformation. Sustainable chemistry goals require replacing conventional noble transition metal catalysts for hydrogenation by earth-abundant base metals. Herein, we report how a practical in situ catalytic system generated by easily available pincer NHC precursors, CoCl2, and a base enabled efficient and high-yielding hydrogenation of a broad range of ketones and aldehydes (over 50 examples and a maximum turnover number [TON] of 2,610). This is the first example of NHC-Co-catalyzed hydrogenation of C=O bonds using flexible pincer NHC ligands consisting of a N-H substructure. Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized by fine-tuning of the steric bulk of pincer NHC ligands. Additionally, a bis(NHCs)-Co complex was successfully isolated and fully characterized, and it exhibits excellent catalytic activity that equals that of the in-situ-formed catalytic system. Catalytic hydrogenation is a powerful tool for the reduction of organic compounds in both fine and bulk chemical industries. To improve sustainability, more ecofriendly, inexpensive, and earth-abundant base metals should be employed to replace the precious metals that currently dominate the development of hydrogenation catalysts. However, the majority of the base-metal catalysts that have been reported involve expensive, complex, and often air- and moisture-sensitive phosphine ligands, impeding their widespread application. From a mixture of the stable CoCl2, imidazole salts, and a base, our newly developed catalytic system that formed easily in situ enables efficient and stereoselective hydrogenation of C=O bonds. We anticipate that this easily accessible catalytic system will create opportunities for the design of practical base-metal hydrogenation catalysts. A practical in situ catalytic system generated by a mixture of easily available pincer NHC precursors, CoCl2, and a base enabled highly efficient hydrogenation of a broad range of ketones and aldehydes (over 50 examples and up to a turnover number [TON] of 2,610). Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized in high selectivities. Moreover, the preparation of a well-defined bis(NHCs)-Co complex via this pincer NHC ligand consisting of a N-H substructure was successful, and it exhibits equally excellent catalytic activity for the hydrogenation of C=O bonds.

Synthesis and reactions of enantiopure substituted benzene cis-hexahydro-1,2-diols

Enantiopure dis-dihydro-1,2-diol metabolites, obtained from toluene dioxygenase-catalysed dis-dihydroxylation of six monosubstituted benzene substrates, have been converted to their corresponding dis-hexahydro-1,2-diol derivatives by catalytic hydrogenation via their dis-tetrahydro-1,2-diol intermediates. Optimal reaction conditions for total catalytic hydrogenation of the dis-dihydro-1,2-diols have been established using six heterogeneous catalysts. The relative and absolute configurations of the resulting benzene dis-hexahydro-1,2-diol products have been unequivocally established by X-ray crystallography and NMR spectroscopy. Methods have been developed to obtain enantiopure dis-hexahydro-1,2diol diastereoisomers, to desymmetrise a meso-cishexahydro-1,2-diol and to synthesise 2-substituted cyclohexanols. The potential of these enantiopure cyclohexanols as chiral reagents was briefly evaluated through their application in the synthesis of two enantiomerically enriched phosphine oxides from the corresponding racemic phosphine precursors.

Process for producing optically active compound

A process for producing an optically active compound based on the hydrolysis of an alkenyl ester compound or the cleavage of an alkenyl ether compound. The process uses neither an acidic compound nor a basic compound, and rectants can be reacted in a high concentration. It does not necessitate a buffer, nutrient, etc. unlike enzymatic reactions or reactions using a microorganism. It is a simple process which attains a satisfactory production efficiency. The process, which is for producing an optically active carboxylic acid or optically active alcohol represented by the general formula (VI): (wherein R1, R2, and R3 are different groups; and A represents methylene, carbonyl, or a single bound), is characterized by causing water to act on an alkenyl ester or alkenyl ether represented by the general formula (I): (wherein R4, R5, and R6 each represents hydrogen, alkyl, etc.) in the presence of a specific transition metal complex having an optically active ligand.

Amber-woody scent: Alcohols with divergent structure present common olfactory characteristics and sharp enantiomer differentiation

Only one out of the four possible trans isomers of the important perfumery alcohol Norlimbanol (1) possesses a very strong amber-woody smell, the isomer 1A with (1′ R,3S,6'S) absolute configuration. Its enantiomer 1B is almost odorless and devoid of amber-woody character, whereas the diastereoisomers 1C and 1D are considerably weaker and perceptible only by the most-sensitive persons. The same is true for a whole series of perceptual analogs of 1, including β-alkoxy alcohols. These ethers belong to two structural classes: [(2,2,6-trimethylcyclohexyl)oxy]- (see 3, 4, and 16) or {[2-(tert-butyl)cyclohexyl]oxy)alkan-2-ol derivatives (see 19 and 20; Table). A superimposition model allowing for good overlap of the respective hydroxylated side chains offers a tentative explanation for the shared perceptual characteristics of the two classes (Fig. 5). The lipophilic cyclohexane moieties present only a minimal overlap in this model, suggesting that quite larger molecules might possess the same smell. (S)-Configured β-alkoxy alcohols can conveniently be obtained on a larger scale by enantioselective reduction of the corresponding ketones (Scheme 9).

Effective nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols using 3β-acetoxyetienic acid, DCC, and DMAP

(1R,2S)-trans-2-Arylcyclohexanols of high enantiomerically purity were obtained by the simple stirring of the corresponding (±)-arylcyclohexanols with 3β-acetoxyetienic acid, DCC, and DMAP at room temperature.