6533b82dfe1ef96bd1292042

RESEARCH PRODUCT

(1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol

subject

description

The title compound, C17H25NO2, was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclohexenylmethanol], followed by the oxirane ring-opening by benzylamine using [Ca(CF3CO2)2] as catalyst under solvent-free condition at 313 K. The molecular conformation is stabilized by an intramolecular O—H...N hydrogen bond. In the crystal, molecules are linked by intermolecular N—H...O hydrogen bonds, forming chains parallel to the a axis, which are further connected by O—H...O hydrogen bonds into sheets parallel to (010). The absolute configuration of the molecule is known from the synthetic procedure.