PHOTOOXYGENATION OF LANOSTERYL ACETATE

PHOTOOXYGENATION OF LANOSTERYL ACETATE
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DOI:
10.1039/p19720000799
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发表时间:
1972-01-01
期刊:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
影响因子:
--
通讯作者:
YOUNG, DW
YOUNG, DW
中科院分区:
其他
文献类型:
--
作者:
FOX, JE;SCOTT, AI;YOUNG, DW

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3β-乙酰氧基甾-8-烯在染料和对硝基苯磺酰氯存在下被光氧化,得到Criegee重排产物3β-乙酰氧基-8,9-环氧-8,9-断链甾-7,9(11)-二烯(XV; R = Ac)和3β-乙酰氧基-7 α-氢过氧化甾-8-烯(VII; R = Ac)。这些化合物被认为是由3β-乙酰氧基-9 α-氢过氧甾-7-烯(II; R = Ac)产生的,并报道了它们的转化。(XV)中的桥连环癸-1,6-二烯体系参与跨环反应。
3β-Acetoxylanost-8-ene has been photo-oxygenated in the presence of a dye and p-nitrobenzenesulphonyl chloride to yield, among other products, the Criegee rearrangement product 3β-acetoxy-8,9-epoxy-8,9-secolanosta-7,9(11)-diene (XV; R = Ac) and 3β-acetoxy-7α-bydroperoxylanost-8-ene (VII; R = Ac). These ARE Thought to arise from 3β-acetoxy-9α-hydroperoxylanost-7-ene (II; R = Ac); their transformations are reported. The bridged cyclodeca-1,6-diene system in (XV) takes part in transannular reactions.