8種のセスキテルペン炭化水素類の塩素化酢酸類を用いる水和反応

概要

論文の詳細を見る
Hydration of sesquiterpene hydrocarbons such as α- and β-selinenes ([1] and [2]), α-guaiene [3], α-burnesene [4], α-patchoulene [5], seychellene [6], β-patchoulene [7] and humulene [8], was investigated with chloroacetic acids (monochloro-, dichloro- or trichloroacetic acid) under different conditions. A mixture of [1] and [2] with equimolar amounts of chloroacetic acids was stirred in a flask with or without dichloroethane at 22_??_95°C for 1_??_60 hr. The hydration of [1] gave α-eudesmol [9] as a sole product, and the hydration of [2] yielded both γ-eudesmol [10] and β-eudesmol [11]. A mixture of [3], [4], [5], [6] and [7] with equimolar amounts of trichloroacetic was stirred in a flask at room temperature for 4 hr. Hydration of [3] gave guaiol [12], [4] gave burnesol [13], and [5] gave an isomerization product [7]. The hydration of [8] with trichloroacetic acid gave humulol [14] in high yield. Stereochemistry of [14] was determined by the variation in the contact shift of each proton using the shift reagent, Eu(dpm)3.
社団法人日本農芸化学会の論文