Abstract: A (Z)-solanone has the steric formula of: or with the name of (S,Z)-5-isopropyl-8-methyl-6,8-diene-2-one or (R,Z)-5-isopropyl-8-methyl-6,8-diene-2-one. A process for the preparation of the (Z)-type solanone and the use thereof in flavoring of cigarette shred are further disclosed. The process includes the following steps: (1) reacting isopentanal and methyl vinyl ketone, under the action of a catalyst and a co-catalyst, to give (S)-2-isopropyl-5-carbonylhexanal or (R)-2-isopropyl-5-carbonylhexanal; (2) reacting the (S)-2-isopropyl-5-carbonylhexanal or the (R)-2-isopropyl-5-carbonylhexanal obtained in step (1) with (iodomethyl)triphenylphosphonium iodide, to give (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or (R,Z)-7-iodo-5-isopropyl-6-ene-2-one; and (3) reacting the (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or the (R,Z)-7-iodo-5-isopropyl-6-ene-2-one obtained in step (2) with pinacol isopropenylborate in the presence of a catalyst to give the (Z)-solanone.

Abstract: A (Z)-solanone has the steric formula of: with the name of (S,Z)-5-isopropyl-8-methyl-6,8-diene-2-one or (R,Z)-5-isopropyl-8-methyl-6,8-diene-2-one. A process for the preparation of the (Z)-type solanone and the use thereof in flavoring of cigarette shred are further disclosed. The process includes the following steps: (1) reacting isopentanal and methyl vinyl ketone, under the action of a catalyst and a co-catalyst, to give (S)-2-isopropyl-5-carbonylhexanal or (R)-2-isopropyl-5-carbonylhexanal; (2) reacting the (S)-2-isopropyl-5-carbonylhexanal or the (R)-2-isopropyl-5-carbonylhexanal obtained in step (1) with (iodomethyl)triphenylphosphonium iodide, to give (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or (R,Z)-7-iodo-5-isopropyl-6-ene-2-one; and (3) reacting the (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or the (R,Z)-7-iodo-5-isopropyl-6-ene-2-one obtained in step (2) with pinacol isopropenylborate in the presence of a catalyst to give the (Z)-solanone.