甾体5-烯-3β-醇在乙醚中用琼斯试剂进行氧化反应。

Oxidation of steroidal 5-en-3 beta-ols with Jones reagent in ether.

作者信息

Solaja B A, Milić D R, Dosen-Mićović L I

机构信息

Faculty of Chemistry, University of Belgrade, Serbia.

出版信息

Steroids. 1994 May;59(5):330-4. doi: 10.1016/0039-128x(94)90122-8.

DOI:10.1016/0039-128x(94)90122-8

Abstract

The two-phase oxidation of steroidal 5-en-3 beta-ol (via 5-en-3-ones) into corresponding 4-en-3,6-diones in diethyl ether with Jones reagent was investigated. It was found that the system Jones reagent/diethyl ether enables short reaction times and easy isolation of the obtained products. The exclusive abstraction of 4 alpha-hydrogen during oxidation, together with molecular mechanics (MM2), and semiempirical (PM3) calculations, suggest that boat conformation of ring A precedes the formation of corresponding radicals (or cations).

摘要

研究了甾体5-烯-3β-醇（通过5-烯-3-酮）在二乙醚中用琼斯试剂两相氧化为相应的4-烯-3,6-二酮的反应。发现琼斯试剂/二乙醚体系反应时间短，所得产物易于分离。氧化过程中4α-氢的专一性提取，结合分子力学（MM2）和半经验（PM3）计算，表明A环的船式构象先于相应自由基（或阳离子）的形成。

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