10411-92-4

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H22O2/c1-9(13)14-11-7-5-10(6-8-11)12(2,3)4/h10-11H,5-8H2,1-4H3/t10-,11+

Upstream product

• 937-05-3 cis-4-tert-butyl-1-cyclohexanol 
• 108-24-7 acetic anhydride 
• 18508-90-2 trans-4-tert-butylmesyloxycyclohexane 
• 3396-11-0 cesium acetate 
• 2163-34-0 trans-4-t-butylcyclohexylamine 
• 64-19-7 acetic acid 
• 21862-63-5 trans-4-tert-butylcyclohexanol 
• 75-36-5 acetyl chloride 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 1900-69-2 trans-4-tert-butylcyclohexyl acetate 
• 15875-99-7 cis-4-tert-butylcyclohexanol methyl ether 
• 2889-74-9 perchlorate d'acetyle 
• 7453-05-6 toluene-4-sulfonic acid-(trans-4-tert-butyl-cyclohexyl ester) 

Downstream Products

• 3178-22-1 tert-butylcyclohexane 
• 1900-69-2 trans-4-tert-butylcyclohexyl acetate 
• 1900-57-8 cis-4-ethoxy-tert-butylcyclohexane 

Relevant academic research and scientific papers

Acid-induced 13C Nuclear Magnetic Resonance Chemical Shift Changes of Ether and Ester Carbon Atoms

13C N.m.r. chemical shifts of ehters dissolved in tetrachloromethane are displaced on addition of trifluoroacetic acid.The displacements result from independent interactions of the acid with the substrate oxygen atoms and alkyl residues.The structure-dependent and stereoselective shift changes are useful for signal assignments, structure determination, conformational analysis, assessment of the distribution of rapidly interconverting conformers of esters, and estimation of the relative basicity of ethers.

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.

Porcine pancreas lipase catalysed acetylation of β-cyclodextrin anchored 4-t-butylcyclohexanol

Porcine pancreas lipase (PPL) catalyzed acetylation of 4-t- butylcyclohexanol gives 10% ester. However, when the latter is included inside hepatakis (2,3,6-tri-O-acetyl)-β-cyclodextrin (β-CD acetate) cavity, this enzymatic reaction affords the highest yield of 86.6%. The enzymatic esterification has been studied as a function of β-CD acetate, PPL and acetic anhydride concentrations. A stoichiometry of 2:1 for 4-t-butylcyclohexanol-β-CD acetate complex is determined. Both trans and cis 4-t-butylcyclohexanol have been found to be acetylated. Gas Chromatographic analysis of the reaction mixtures shows that trans/cis ratios of the esters formed varied from 2.1 to 4.34.

A PROCEDURE FOR ALCOHOL INVERSION USING CESIUM ACETATE

A convenient and efficient procedure for alcohol inversion by means of the reaction of mesylates or alkyl halides with cesium acetate is described.

2-Norbornanediazonium Ions Revisited

The reactions of 2-norbornanediazonium ions have been reinvestigated with the aid of optically active and deuterium-labeled precursors.Enantiomeric purities were determined by direct VPC methods, and deuterium distributions by 2H NMR spectroscopy.The product pattern is strongly affected by the polarity of the solvent. exo-Diazonium ions 13 in water yield racemic exo alcohol (s,kΔ) of the norbornadiazonium ions.Optically active exo products are typical of nonpolar solvents and originate most probably from assymetric ion pairs.Model studies with optically active bicyclooct-3-en-2-amine (36) provide conclusive evidence that ion-pair colapse may lead to optically active products even in the case of delocalized achiral carbocations.

Solvent and Gas-phase Effects on the Equilibrium between Configurational Isomers of Some 4-t-Butylcyclohexanes

Through a combination of gas chromatographic head space analysis, gas chromatography retention times, and calorimetrically determined enthalpies of solution, the effect of various solvents, relative to the gas phase, on values of ΔG0, ΔH0, and ΔS0 for the equilibrium between r-1,t-2-dibromo-c-4- and r-1,t-2-dibromo-t-4-t-butylcyclohexane has been determined.It is shown that the more polar diequatorial dibromo-isomer is stabilised relative to the diaxial isomer both in terms of Gibbs energy and enthalpy in polar media.Although values of ΔG0, ΔH0, and ΔS0 for the equilibrium in nonpolar solvents approach the gas-phase values, there are still noticeable differences in these thermodynamic parameters between the gas phase and solvents such as hexane and cyclohexane.The effects of various media on ΔG0 values for the equilibria between cis- and trans-4-t-butylcyclohexyl bromide and cis- and trans-4-t-butylcyclohexyl acetate have also been determined, but values of ΔG0 for these two equilibria are largely independent of the reaction medium.