摘要
以叔丁基过氧化氢(TBHP)和次氯酸钠氧化α-紫罗兰酮,得到关键中间体3-氧代-α-紫罗兰酮(1),同时,进行了条件试验,最佳条件为:在室温条件下,无水乙腈和K2CO3中,n(α-紫罗兰酮):n(TBHP)∶n(NaCl O)为1∶8∶3时,反应得到产物,最佳得率为50.9%。产物再经硼氢化钠选择性还原得氧代紫罗兰醇,经乙酸酐酯化得目标产物3-氧代-α-紫罗兰醇乙酸酯,总收率为32.66%。同时,也进行了4-氧代-β-紫罗兰醇乙酸酯的合成,总收率为31.32%。此方法原料易得,毒性小,成本低,反应操作简便,容易进行。所有中间体及产物的结构经IR,1H NMR,13C NMR和MS证实。
3-Oxo-ionone(1) was prepared by the oxidation of α-ionone with t-butyl hydroperoxide and NaClO in the solvent of acetonitrile and K2CO3.The optimized molar ratio of n(α-ionone)∶n(TBHP)∶n(NaClO) was 1∶8∶3.The yield was 50.9%.It was reduced by NaBH4 and subsequent esterificated by acetic anhydride to give 3-oxo-α-ionol acetate.The total yield was 32.66%.Meanwhile,4-oxo-β-ionol acetate was prepared by the same method.The total yield was 31.32%.This procedure has the advantages of easy to get starting materials,mild reaction conditions and convenient operations.The intermediate and product were characterized by IR、1H NMR、13C NMR and MS.
出处
《化学世界》
CAS
CSCD
北大核心
2011年第5期299-302,共4页
Chemical World
基金
上海市教委科学基金资助项目(050Z17)