STEROIDS AND STEROIDASES: III. DICYCLOHEXYLCARBODIIMIDE–DIMETHYL SULFOXIDE OXIDATIONS OF ALCOHOLS AND THIOLS
STEROIDS AND STEROIDASES: III. DICYCLOHEXYLCARBODIIMIDE–DIMETHYL SULFOXIDE OXIDATIONS OF ALCOHOLS AND THIOLS
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类固醇和类固醇酶：III.二环己基碳二亚胺-二甲基亚砜氧化醇和硫醇
DOI：
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发表时间：
1966
期刊：
影响因子：
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通讯作者：
D. C. Wigfield
中科院分区：
文献类型：
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作者：
J. B. Jones;D. C. Wigfield
对酸碱不稳定类固醇 Δ5-3-酮的制备方法的调查表明，用二环己基碳二亚胺-二甲亚砜（Moffatt 试剂）氧化适当的 Δ5-3β-醇是最令人满意的，所需酮的产率为 60-70%，几乎没有或没有异构化为相应的 Δ4-3-酮。从3β-羟基雄雄-5-en-17-酮的氧化中，分离出Pummerer重排的产物3β-(甲硫基甲氧基)-雄雄-5-en-17-酮。 Moffatt 试剂也方便将硫醇氧化成相应的二硫化物。
A survey of methods for the preparation of acid- and base-labile steroid Δ5-3-ketones showed that oxidation of the appropriate Δ5-3β-alcohols with dicyclohexylcarbodiimide–dimethyl sulfoxide (Moffatt reagent) was the most satisfactory, giving yields of 60–70% of the required ketones with little or no isomerization to the corresponding Δ4-3-ketones. From the oxidation of 3β-hydroxyandrost-5-en-17-one, the product of a Pummerer rearrangement, 3β-(methylthiomethoxy)-androst-5-en-17-one, was isolated. The Moffatt reagent also was convenient for the oxidation of thiols to the corresponding disulfides.