7-甲氧基-3′-羟基黄酮的合成及其紫外光谱性能
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TQ 203.2

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陕西省科技厅社发攻关项目(2021SF-382);陕西省教育厅项目(21JK0569,21JS003);陕西理工大学2022年研究生创新(SLGYCX2227)。


Synthesis of 7-Methoxyl-3"-hydroxyflavones and Its Ultraviolet Spectral Properties
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    摘要:

    碱催化下间羟基苯甲醛和丹皮酚发生缩合反应,经紫外、红外、元素分析及核磁共振谱等综合分析确定产物为2",3-二羟基-4"-甲氧基查尔酮,产率为82.2%,克服了缩合反应中需要保护羟基的问题;再在高温下以DMSO为溶剂碘催化诱导2",3-二羟基-4"-甲氧基查尔酮关环得到7-甲氧基-3"-羟基黄酮,产率为92.0%,实现了7-甲氧基-3"-羟基黄酮的高效合成。考察2",3-二羟基-4"-甲氧基查尔酮和7-甲氧基-3"-羟基黄酮在不同浓度酸碱盐溶液的紫外光谱的变化,2",3-二羟基-4"-甲氧基查尔酮在浓度为4 mol?L-1 HCl溶液中发生反应,也能与低浓度NaOH溶液发生反应,生成物在30 min内能稳定存在;易与KNO3溶液发生反应,反应程度随KNO3溶液浓度增大而增大,生成物不能长时间稳定存在,7-甲氧基-3`-羟基黄酮可在HCl、NaOH、KNO3溶液中能长时间稳定存在。

    Abstract:

    2",3-Dihydroxy-4"-methoxychalcone was synthesized by the condensation reaction with 3-hydroxybenzaldehyde and paeonol occurred under the alkaline catalysis, this product molecular structure was determined by comprehensive analysis such as UV, IR, elemental analysis and NMR including of 1HMNR, 13C NMR and 135°dept, its yield was 82.2%, then and 7-methoxy-3"-hydroxyflavone was synthesized by base iodine catalyzed closing ring reactions to 2",3-dihydroxy-4"-methoxychalcone with DMSO as solvent at high temperature, the flavones" yield was 92.0%, this synthetic reaction could overcome the problem of protecting the hydroxyl group in the condensation reaction and realized the efficient synthesis of 7-methoxy-3"-hydroxyflavone. The changes of UV spectra of 2",3-dihydroxy-4"-methoxychalcone and 7-methoxy-3"-hydroxyflavone were investigated in acid, alkali and salt solutions of their different concentrations respectively, 2",3-dihydroxy-4"-methoxychalcone could react in HCl solution of 4 mol?L-1 concentration, and also reacted in low-concentration NaOH solution, its variable substance could exist stably within 30 min, it easily reacted in KNO3 solution, the degree of reaction increased with the increase of the concentration of KNO3 solution and this variable substance could not exist stably for a long time. 7-methoxy-3"-hydroxyflavone could exist stably in HCl, NaOH and KNO3 solutions of their different concentrations for a long time.

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王乙颖,安超娜,姚甜,等. 7-甲氧基-3′-羟基黄酮的合成及其紫外光谱性能[J]. 科学技术与工程, 2023, 23(17): 7458-7467.
Wang Yiying, An Chaona, Yao Tian, et al. Synthesis of 7-Methoxyl-3"-hydroxyflavones and Its Ultraviolet Spectral Properties[J]. Science Technology and Engineering,2023,23(17):7458-7467.

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  • 收稿日期:2022-06-14
  • 最后修改日期:2023-03-07
  • 录用日期:2023-03-15
  • 在线发布日期: 2023-06-28
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