Study of syntheses and specific rotations of (S)-3-phenylhexan-3-ol and its derivatives

Tertiary alcohols, 3-phenylhexan-3-ol and 3-methylhexane-3-ol, and their derivatives were synthesized. The reaction conditions of the esterification of the tertiary alcohol with 2-NO2PhCO2Cl and 4-NO2PhCO2Cl were optimized. The absolute configuration of the derivative from (S)-3-phenylhexan-3-ol was identified by X-ray study and computational methods. Experimental results confirmed the computational specific rotation predictions by DFT-based and matrix methods.

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(S)-3-Phenylhexan-3-olC12H18O[α]D = +11.6 (c 0.00805, CHCl3)Absolute configuration: (S)

(S)-3-Phenylhexan-3-yl-4-nitrobenzoateC19H21NO4[α]D = +1.6 (c 0.026, CHCl3)Absolute configuration: (S)

(S)-3-Phenylhexan-3-yl 4-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanamido)benzoateC30H42N2O5[α]D = −33.3 (c 0.01485, CHCl3)Absolute configuration: (S)