摘要
报道了一种2-羟基-3-(3-氧代-1,3-二苯基丙基)萘-1,4-二酮的合成方法。以2-羟基萘醌-1,4-二酮和(E)-查尔酮为原料通过Michael加成反应合成得到标题化合物2-羟基-3-(3-氧代-1,3-二苯基丙基)萘-1,4-二酮,采用MS、1H NMR和13C NMR对其化学结构进行验证,并考察了反应条件。n(查尔酮):n(2-羟基-1,4-萘醌)=1.1:1;TEA用量为n(TEA):n(2-羟基-1,4-萘醌)=0.20:1;以二氯甲烷为溶剂,25℃,反应45 min为最佳反应条件,此时产物1a收率为92.9%。对反应底物进行拓展,该最佳反应工艺条件被用于1-(3-羟基-1,4-二氧代-1,4-二羟基萘-2-基)肼-1,2-二羧酸二异丙酯1b的合成,收率达到94.4%。
2-Hydroxy-3-(3-oxo-1,3-diphenylpropyl)naphthalene-1,4-dione was synthesized by the Michael addition reaction of 2-hydroxynaphthalene-1,4-dione and(E)-chalcone in the presence of triethylamine as catalyst.The structure of the product was confirmed by 1 H NMR,13 C NMR and MS.The optimal reaction conditions were investigated,and target compound 1 a was obtained in the yield of 92.9%when n(chalcone):n(2-hydroxynaphthalene-1,4-dione)was 1:1.1,n(TEA):n(2-hydroxynaphthalene-1,4-dione)was 0.20:1,dichloromethane was used as solvent,the reaction temperature was 25℃and the reaction time was 45 min.The synthesis method was used for synthesis of diisopropyl 1-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)hydrazine-1,2-dicarboxylate 1 b,and the yield reached 94.4%.
作者
唐文强
高艳蓉
刘斌
张翠亚
何志鹏
TANG Wen-qiang;GAO Yan-rong;LIU Bin;ZHANG Cui-ya;HE Zhi-peng(School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Shaanxi Xi’an 712046,China;Shaanxi Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine,Shaanxi Xi’an 712046,China)
出处
《当代化工》
CAS
2020年第5期794-797,共4页
Contemporary Chemical Industry
基金
陕西省教育厅专项科研计划项目(19JK0101)
陕西省高校科协青年人才托举计划项目,项目号:20180312
陕西国际商贸学院中药质量标志物创新团队(SSY18TD02)
陕西国际商贸学院省级平台招标项目(2019XT-1-02)
关键词
萘醌衍生物
3-取代-2-羟基萘醌
MICHAEL加成
合成
Naphthaquinone derivatives
3-substituted 2-hydroxynaphthalene-1,4-dione
Michael addition reaction
Synthesis
