CAJ | 학술논문

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)。
이파동산위원료,경Willgerodt반응합성료고파산,산품수솔체도62%。대고파산산물진행료IR화1H NMR결구분석여표정。고파산재경선록화、친핵취대、친핵가성반응,합성료5충쌍선기류뇨연생물,수솔체도65%~80%。소합성적5충쌍선기류뇨연생물산품경IR、1H NMR진행료결구감정,분별위2,2′-(2,2-이갑기배정기-1,3-이기)쌍[N-(분기안기류대갑선기)을선알](5a)、2,2′-(2,2-이갑기배정기-1,3-이기)쌍[N-(린갑분기안기류대갑선기)을선알](5b)、2,2′-(2,2-이갑기배정기-1,3-이기)쌍[N-(간갑분기안기류대갑선기)을선알](5c)、2,2′-(2,2-이갑기배정기-1,3-이기)쌍[N-(대갑분기안기류대갑선기)을선알](5d)화2,2′-(2,2-이갑기배정기-1,3-이기)쌍[N-(2,4-이갑기분기안기류대갑선기)을선알](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).