高蒎酸及其双酰基硫脲衍生物的合成及表征

Synthesis and Characterization of sym-Homopinic Acid and Its Diacylthioureas Derivatives

以蒎酮酸为原料,经Willgerodt反应合成了高蒎酸,产品收率达到62%。对高蒎酸产物进行了IR和1H NMR结构分析与表征。高蒎酸再经酰氯化、亲核取代、亲核加成反应,合成了5种双酰基硫脲衍生物,收率达到65%~80%。所合成的5种双酰基硫脲衍生物产品经IR、1H NMR进行了结构鉴定,分别为2,2′-（2,2-二甲基环丁基-1,3-二基）双[N-（苯基氨基硫代甲酰基）乙酰胺]（5a）、2,2′-（2,2-二甲基环丁基-1,3-二基）双[N-（邻甲苯基氨基硫代甲酰基）乙酰胺]（5b）、2,2′-（2,2-二甲基环丁基-1,3-二基）双[N-（间甲苯基氨基硫代甲酰基）乙酰胺]（5c）、2,2′-（2,2-二甲基环丁基-1,3-二基）双[N-（对甲苯基氨基硫代甲酰基）乙酰胺]（5d）和2,2′-（2,2-二甲基环丁基-1,3-二基）双[N-（2,4-二甲基苯基氨基硫代甲酰基）乙酰胺]（5e）。

Five new diacylthioureas were obtained with the yields of 65% - 68% through acylchlorination, nucleophilic substitution, nucleophilic addition reactions from sym-homopinic acid which was obtained from pinonic acid via Willgerodt reaction. Their structures were characterized by IR and 1H NMR spectra. The products were as follows：2, 2′-（ 2, 2-dimethylcyclobutane-1,3-diyl）bis[N-（phenylcarbamothioyl）acetamide]（5a）,2,2′-（2,2-dimethylcyclobutane-1,3-diyl）bis[N-（o-tolylcarbamothioyl）acetamide]（5b）,2,2′-（2,2-dimethylcyclobutane-1,3-diyl）bis[N-（m-tolylcarbamothioyl）acetamide] （5c）,2,2′-（2,2-dimethylcyclobutane-1,3-diyl）bis[N-（p-tolylcarbamothioyl）acetamide]（5d）,2,2′-（2,2-dimethylcyclobutane-1,3-diyl）bis[N-（2,4-dimethylpheny）phenylcarbamothioyl acetamide]（5e）.