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由2′,4′-二氢-6′-甲氧基-3′,5′-二甲基查耳酮合成新黄酮(英文) 被引量：1

Synthesis of New Flavonoids from 2′,4′-Dihydroxy-6′-methoxy-3′,5′-dimethylchalcone
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摘要 在DMSO/I2的氧化作用下,由2′,4′-二氢-6′-甲氧基-3′,5′-二甲基查耳酮可合成一种全新结构的黄酮:7-羟基-5-甲氧基-6,8-二甲基黄酮(产率91%),而在HCl/MeOH作用下则得到了两种黄烷酮:7-羟基-5-甲氧基-6,8-二甲基黄烷酮(产率70%)和5,7-二羟基-6,8-二甲基黄烷酮(产率20%)。 A new flavone, 7-hydroxy-5-methoxy-6,8-dimethylflavone, was synthesized in 91% yield by treating of 2＇,4＇-dihydroxy-6＇-methoxy-3＇ ,5 ＇-dimethylehaleone （ 1 ） with D MSO/I2. Two other flavonoids, 7-hydroxy-5-methoxy-6, 8-dimethylflavanone and 5, 7-dihydroxy-6, 8-dimethylflavanone, were obtained from 1 in HCI/MeOH solution in 70% and 20% yield, respectively.
作者 张剑锋 江峰 周雄
机构地区 宁波大学材料科学与化学工程学院新型功能材料及其制备科学国家实验室重点培育基地
出处 《合成化学》 CAS CSCD 2007年第3期319-321,349,共4页 Chinese Journal of Synthetic Chemistry
基金 Supported by the Plan of High Learning Young Teacher of Zhejiang Provice Supported by the Ningbo Youth Science Fund Project(2005A620015)
关键词 查耳酮 黄烷酮 黄酮 合成 chalcone flavone flavanone flavonoids synthesis
分类号 O626 [理学—有机化学]
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参考文献14

  • 1Ducki S,Forrest R,Hadfield J A,et al.Potent antimitotic and cell growth inhibitory properties of substituted chalcones[J].Bioorg Med Chem Lett,1998,8:1051-1056.
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同被引文献13

  • 1汪秋安,周强,范华芳.7-羟基黄酮醇和7-羟基黄烷酮及其衍生物的合成[J].合成化学,2007,15(1):50-54. 被引量：4
  • 2Herencia F, FerrandizM L, Ubeda A, et al. Synthesis and anti-inflammatory activity of chalcone derivatives [J]. Bioorg Med Chem Lett,1998 ,8:1169 - 1174.
  • 3L iuM, Wilairat P, GoM L. Antimalarial alkoxylated and hydroxylated chalcones: Structure-activity relationship analysis [ J ]. J Med Chem ,2001,44 :4443 - 4452.
  • 4Nielsen S F, Christensen S B, Cruiani G, et al. Antileishmanial chalcones: Statistical design, synthesis and three-dimensional quantitative structure-activity relationship analysis [ J ]. J Meal Chem ,1998 ,41:4819 -4832.
  • 5Bois F, Boumendjel A, Mariotte A, et al. Synthesis and biological activity of 4-alkoxychalcones: Potential hydrophobic modulators of P-glycoprote in-mediated muhidrug resistance [ J ]. Bioorg Med Chem, 1999,7 : 2691 - 2695.
  • 6Tomas W, Barberan F A, CliffordM N. Flavanones, chalcones and dihydrochalcones-nature, occurrence and dietary burden[J].J Sci Food Agric,2000,80:1073 - 1080.
  • 7V Seidel, F Bailleul, P G Waterman. (Rel)-1,2-di-(2, 4-dihydroxy-6-methoxybenzoyl )-3, 4-di-( 4-me- thoxyphenyl)-cyclobutane and other flavonoids from the aerial parts of Goniothalamus gardneri and Goniothalamus thwaitesii [ J ]. Phytochemistry, 2000, 55 (5) :439 -446.
  • 8C Marais, W J Rensburg, D Ferreira, et al. (S)- and ( R )-erlodictyol-6-C-beta-D-glucopyranoside, novel keys to the fermentation of rooibos (Aspalathus linearls) [J]. Phytochemistry,2000,55( 1 ) :43 -49.
  • 9Y Leong, L J Harrison, G J Bennett, et al. A dihydrochaleone from Lindera lucida [ J ]. Phytoehemisty, 1998,47 (5) : 891 - 894.
  • 10Jr J Dudash, X Zhang, R E Zeck, et al. Glycosylated dihydrochalcones as potent and selective sodium glucose co-transporter 2 ( SGLT 2 ) inhibitors [ J ]. Bioorganic & Medicinal Chemistry Letters, 2004, 14 (20) :5121 -5125.

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合成化学
2007年 第3期

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