508170-84-1

Usage

Group

1,2-cyclohexanediol compounds

Usage

Production of pharmaceuticals, cosmetics, and other consumer products

Stereo-specific isomer

(1R,2R)-relconfiguration

Primary use

Intermediate or starting material in the synthesis of various organic compounds

Applications

Reagent in organic chemistry reactions, building block for specific chemical products

Safety measures

Appropriate handling and precautions required due to potential uses in various industries

Relevant academic research and scientific papers

Formation and characterization of a multicomponent equilibrium system derived from cis- and trans-1-aminomethylcyclohexane-1,2-diol

Both cis and trans isomers of amino diols 3-6 were prepared stereoselectively. In the reactions between 3-6 and phenyl isothiocyanate, the ring closure proceeded regioselectively and resulted only in spiro derivatives of 2-phenyliminooxazolidines 9, 10, 13, and 14. The reaction of cis-(or trans-)1-aminomethylcyclohexane-1,2-diol 4 (or 6) with 1 equiv of an aromatic aldehyde 15a-g in EtOH at room temperature resulted in a complex, multicomponent equilibrium mixture of 16a-g and 18a-g (or 17a-g and 19a-g), in each case consisting of a five-component, ring-chain tautomeric system 16A-E (or 17A-E), involving the Schiff base, two epimeric spirooxazolidines, two epimeric condensed 1,3-oxazines, and some of the four tricyclic compounds 18A-D (or 19A-D). The five-component, ring-chain equilibria were found to be adequately described by the Hammett-Brown linear free energy equation.