22241-34-5

Basic information

• Product Name: 1,2-Cyclohexanediol, monoacetate
• CAS NO: 22241-34-5
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Mol File: 22241-34-5.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: 1,2-Cyclohexanediol, monoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclohexanediol, monoacetate(22241-34-5)
• EPA Substance Registry System: 1,2-Cyclohexanediol, monoacetate(22241-34-5)

Safety Data

• Hazardous Substances Data: 22241-34-5(Hazardous Substances Data)

Upstream product

• 1759-71-3 trans-1,2-cyclohexanediol diacetate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 141-78-6 ethyl acetate 
• 110-83-8 cyclohexene 
• 108-05-4 vinyl acetate 
• 62921-46-4 trans-2-acetoxy-1-cyclohexanol 
• 64-19-7 acetic acid 
• 286-20-4 cyclohexene oxide 
• 127-09-3 sodium acetate 
• 5011-76-7 2-acetoxy-2-cyclohexen-1-one 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 1792-81-0 cis-1,2-cyclohexane 

Downstream Products

• 131139-94-1 (1'R,2'R,3S)-2'-hydroxycyclohexyl 3-methylheptanoate 
• 131140-03-9 (1R,2R)-2-hydroxycyclohexyl (E)-cinnamate 
• 131140-04-0 (1R,2R)-2-hydroxycyclohexyl (E)-2-pentenoate 
• 131140-02-8 (1R,2R)-2-hydroxycyclohexyl crotonate 
• 64363-90-2 (+)-(2R)-2-acetoxycyclohexanone 
• 17472-04-7 2-acetoxycyclohexanone 
• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 

Relevant articles and documents

ONE-POT CONVERSION OF O-ACETYLSUGAR LACTONES INTO 2,3-DIDEOXYSUGAR DERIVATIVES VIA PLATINUM-CATALYZED HYDROGENOLYSIS

O-Acetylsugar lactones were cleanly converted into the corresponding 2,3-dideoxysugar derivatives at room temperature under an atmospheric pressure of hydrogen in the presence of triethylamine and platinum catalysts.

Uncovering Key Structural Features of an Enantioselective Peptide-Catalyzed Acylation Utilizing Advanced NMR Techniques

We report on a detailed NMR spectroscopic study of the catalyst-substrate interaction of a highly enantioselective oligopeptide catalyst that is used for the kinetic resolution of trans-cycloalkane-1,2-diols via monoacylation. The extraordinary selectivity has been rationalized by molecular dynamics as well as density functional theory (DFT) computations. Herein we describe the conformational analysis of the organocatalyst studied by a combination of nuclear Overhauser effect (NOE) and residual dipolar coupling (RDC)-based methods that resulted in an ensemble of four final conformers. To corroborate the proposed mechanism, we also investigated the catalyst in mixtures with both trans-cyclohexane-1,2-diol enantiomers separately, using advanced NMR methods such as T1relaxation time and diffusion-ordered spectroscopy (DOSY) measurements to probe molecular aggregation. We determined intramolecular distance changes within the catalyst after diol addition from quantitative NOE data. Finally, we developed a pure shift EASY ROESY experiment using PSYCHE homodecoupling to directly observe intermolecular NOE contacts between the trans-1,2-diol and the cyclohexyl moiety of the catalyst hidden by spectral overlap in conventional spectra. All experimental NMR data support the results proposed by earlier computations including the proposed key role of dispersion interaction.

Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification

We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.