孕烯醇酮衍生物的合成

Synthesis of Pregnenolone Derivatives

研究了孕烯醇酮衍生物的合成.以孕烯醇酮为原料在甲酸中以质量分数30%过氧化氢溶液氧化、甲醇中碱水解得3β,5α,6β-三羟基孕甾-20-酮,再以3β,5α,6β-三羟基孕甾-20-酮与异丙基溴化镁在无水四氢呋喃中室温反应5 h,然后加入质量分数10%的硫酸继续反应约1 h,得20-异丙基孕甾-3β,5α,6β,20-四醇,收率11.6%,m.p.168~170℃.孕烯醇酮与乙基溴化镁经相似的格氏反应条件得20-乙基孕甾-3β,20-二醇,收率36.4%,m.p.198~199℃.以上化合物经IR和/或~1H-NMR确证结构正确.

To synthesize the derivatives of pregnenolone,3β,5α,6β-trihydroxy pregn-20-one was synthesized using pregnenolone as raw material through mass fractional 30%H 2O 2 oxidation in formic acid.20-isopropyl pregn-3β,5α,6β,20-tetraol was synthesized from 3β,5α,6β-trihydroxypregn-20-one and isoproyl magnesium bromide through Grignard reaction at room temperature in anhydrous THF for 5h,and then continuing for 1 h after addition of mass fractional 10%sulfuric acid solution.The yield was 11.6%and the melting point was 168~170℃.20-Ethyl pregn-5-ene-3β,20-diol was synthesized from pregnenolone and ethyl magnesium bromide through similar Grignard reaction condition,The yield was 36.4%and the melting point was 198~199℃.Above compounds were corroborated structurally by using IR and/or 1H-NMR.