Rearrangement of 5-O-prenyl flavones:: a regioselective access to 6-C-(1,1-dimethylallyl)- and 8-C-(3,3-dimethylallyl)-flavones

Rearrangement of 5-O-prenyl flavones:: a regioselective access to 6-C-(1,1-dimethylallyl)- and 8-C-(3,3-dimethylallyl)-flavones
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DOI:
10.1016/s0040-4039(01)01503-9
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发表时间:
2001-10-08
影响因子:
1.8
通讯作者:
Barron, D
Barron, D
中科院分区:
化学4区
文献类型:
--
作者:
Daskiewicz, JB;Bayet, C;Barron, D

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采用微波辐照技术对7- memo -5-戊烯基菊花素的Claisen重排进行了区域选择性控制。产物的性质受辐照功率和溶剂类型的影响。在750 W的N,N-二乙基苯胺中辐照可以产生8-(3,3-二甲基丙烯基)对重排产物,而在N,N-二乙基丁胺中回流可以选择性地获得6-(1,1-二甲基丙烯基)对重排化合物。2001爱思唯尔科学有限公司版权所有。
Regioselective control of the Claisen rearrangement of 7-MEM-5-prenyl chrysin was achieved by microwave irradiation. The nature of the products was influenced by the irradiation power and the type of solvent. Irradiation at 750 W in N,N-diethylaniline specifically yielded the 8-(3,3-dimethylallyl) para-rearranged product while refluxing in N,N-diethylbutylamine gave selective access to the 6-(1,1-dimethylallyl) ortho-rearranged compound. (C) 2001 Elsevier Science Ltd. All rights reserved.