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目的为改进氧甲氢龙的合成工艺及提高产率提供实验依据。方法通过柱色谱、重结晶等方法分离纯化合成氧甲氢龙过程中发现的副产物,经IR、1H-NMR、13C-NMR、MS、元素分析、X-单晶衍射实验等分析手段确证副产物的化学结构;推测副产物的形成机制并按此机制合成该副产物。结果与结论鉴定副产物为2-(2-羟基乙氧基)-17β-羟基-2,17α-二甲基-A-失碳-5α-雄甾烷,其形成机制可能是格氏试剂形成的甲基负离子在进攻中间体(7)17位的羰基碳的同时,一部分的甲基负离子从甾体平面结构的下方进攻了2位的乙缩酮的碳原子进而生成该副产物。准确分析出副产物的化学结构及形成机制。
OBJECTIVE To provide experimental basis for improving the synthesis process and improving the yield of oxydine. Methods The by-products were isolated and purified by column chromatography and recrystallization. The compounds were confirmed by IR, 1H-NMR, 13C-NMR, MS, elemental analysis and X-ray diffraction. The chemical structure of the product; the formation mechanism of the byproduct is speculated and the byproduct is synthesized according to this mechanism. RESULTS AND CONCLUSIONS The by-product was identified as 2- (2-hydroxyethoxy) -17β-hydroxy-2,17α-dimethyl-A-nor-5α-androstane and its formation mechanism may be Grignard reagent formation Methyl anion While attacking the carbonyl carbon at position 17 of intermediate (7), a portion of the methyl anion attacks the carbon atom of the 2-position acetal from below the steric planar structure to generate this by-product. Accurately analyze the chemical structure and formation mechanism of by-products.