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Thesis Advisor赵文军 ; 高林
Degree Grantor中国科学院研究生院
Place of Conferral北京
Degree Discipline有机化学
Keyword孕马尿 雌酮 马烯雌酮 合成

孕马结合态雌激素是从孕马尿里提取的天然雌激素,在医学上主要应用于雌激素替代疗法。分析手段的提高推动了孕马尿的成份分析的深入探索,目前已知有200种以上成分。从上世纪三十年代至今,孕马雌激素的主要成分的合成研究一直是国内外研究热点。雌酮、马烯雌酮和17α-二氢马烯雌酮是美国药典规定的孕马雌激素的三个指标性化合物,而我国的孕马尿中17α-二氢马烯雌酮的含量偏低于美国药典指标,故利用天然原料实现人工合成17α-二氢马烯雌酮有一定的应用价值。本文主要探讨了雌酮的B环衍生物的合成,用于进一步合成孕马雌激素的另外两个重要成分17α-二氢马烯雌酮和马烯雌酮。采用两条合成路线得到14个重要合成中间体,各步反应条件得以优化。寻找到新的方法将B环饱和的甾体雌激素合成转化为B环不饱和的甾体雌激素;同时发现可在温和的反应条件下将A环芳香化的甾体雌激素转化为A环非芳香性化合物的方法。 本文系统研究了雌酮B环衍生物的合成方法,为后期实现17α-二氢马烯雌酮和马烯雌酮的合成奠定了基础。

Other Abstract
The conjugated estrogenic mixture extracted from Pregnant Mares’ Urine(PMU) is chiefly used for hormone replacement therapy (HRT) in the medical service. There are two hundred compounds in Pregnant Mares’ Urine. The extensive research programs directed toward the total synthesis of the female sex hormone were well under way in 1935. US Pharmacopeia(USP)has been added to estrone, equilin and 17α-dihydroequilin as the most important compounds of PMU. But the 17α-dihydroequilin in the PMU originated from Xinjiang is failed to meet the USP requirements, so the synthesis of it is imperative. Synthesis of derivatives of estrone used to synthesis of 17α-dihydroequilin have been studied in this dissertation. The key work is to introduce an unsaturated bond into the B ring of steroid. However, it should be noted that the formation of unsaturated B ring of steroid from △7-ketosteroids has been not observed previously. The thesis is aimed to synthesize the 17α-dihydroequilin by two strategies and some important synthetic intermediates. Additional a synthetic approach to introduce unsaturated bonds into the B ring of steroid were accomplished. Occasionally a methodology of conversation the A ring to the non- aromatic ring in mild condition has been found. All the work above have been a good preparation of the later synthetic work, which is very helpful to the export of the domestic PMU.
Document Type学位论文
Recommended Citation
GB/T 7714
王丽. 雌酮B环衍生物的合成研究[D]. 北京. 中国科学院研究生院,2008.
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