CAS: 855-97-0; 2-(3,4-Dimethoxyphenyl)-5,7-Dimethoxy-4H-Chromen-4-One

该化合物是一种聚甲基苯氧基氟化酮衍生物,其特征是位于5,7,3'和4'的四种甲氧基替代物.该化合物由于其混合氧化结构,增加了对新陈代谢降解的抗药性,因此具有显著的稳定性.它是分析化学中用于氟氯素定量和识别的宝贵参考标准.其定义明确的结构和高纯度使它适合研究应用,特别是研究氟氯素代谢,生物利用率和结构活动关系.该化合物的亲脂性也促进了其在薄膜渗透性研究中的使用.其一贯的物理化学特性确保了实验环境中的再生性.

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物理性质

MSDS等安全信息

上下游产品

diazomethane velutin 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on dimethyl sulfate Veratric acid 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone quercetol retusin

合成工艺路线路线简述

  • 合成目标产物 3',4',5,7-Tetramethoxyflavone 主要起始原料 2''-Hydroxy-3,4,4'',6''-Tetramethoxychalcone
  • 29080-58-8 = 855-97-0
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; Rt; Rt -> Reflux; 2 H,Reflux
    标题:Regioselective Hydroxylation Of 2-Hydroxychalcones By Dimethyldioxirane Towards Polymethoxylated Flavonoids
    作者:Chu,Han-Wei; Et Al
    参考文献:Tetrahedron 日期:2004 卷标:60(11) 页码:2647-2655]

    114021-60-2 = 855-97-0
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 20 Min,Reflux
    标题:New Synthesis Of 5,7-Dimethoxyflavone And 5,7,3',4'-Tetramethoxyflavone
    作者:Sultana,Rajia; Et Al
    参考文献:Oriental Journal Of Chemistry 日期:2006 卷标:22(1) 页码:77-82]

    10496-67-0 = 855-97-0
    反应条件:1.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 2 H,Reflux
    标题:Synthesis Of Chlorinated Flavonoids With Anti-Inflammatory And Pro-Apoptotic Activities In Human Neutrophils
    作者:Freitas,Marisa; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2014 卷标:86 页码:153-164]

    10496-67-0 = 855-97-0
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 12 H,110 °C
    标题:Anti-Melanogenic Properties Of Velutin And Its Analogs
    作者:Jung,Se-Hui; Et Al
    参考文献:Molecules 日期:2021 卷标:26(10)]

    17060-20-7 = 855-97-0
    反应条件:1.1 Reagents: 1-Hydroxy-1,2-Benziodoxol-3(1H)-One 1-Oxide (Polymer Supported) Solvents: Dimethyl Sulfoxide; 90 °C
    标题:Selective And Efficient Oxidative Modifications Of Flavonoids With 2-Iodoxybenzoic Acid (Ibx)
    作者:Barontini,Maurizio; Et Al
    参考文献:Tetrahedron 日期:2010 卷标:66(32) 页码:6047-6053]

    71847-57-9 = 855-97-0
    反应条件:1.1 Reagents: Sulfuric Acid Solvents: Acetic Acid; 1 H,110 °C
    标题:Exploring Quercetin And Luteolin Derivatives As Antiangiogenic Agents
    作者:Ravishankar,Divyashree; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2015 卷标:97 页码:259-274]

    491-70-3 = 855-97-0
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 12 H,Rt
    标题:Structural Requirements Of Flavonoids And Related Compounds For Aldose Reductase Inhibitory Activity
    作者:Matsuda,Hisashi; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2002 卷标:50(6) 页码:788-795]

    365564-10-9 + 54107-66-3 = 855-97-0
    反应条件:1.1 Reagents: Oxygen Catalysts: 5-Nitro-1,10-Phenanthroline,Palladium Trifluoroacetate Solvents: Dimethyl Sulfoxide; 48 H,100 °C
    标题:A Versatile Approach To Flavones Via A One-Pot Pd(Ii)-Catalyzed Dehydrogenation/oxidative Boron-Heck Coupling Sequence Of Chromanones
    作者:Lee,Jun; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2016 卷标:14(2) 页码:777-784]

    365564-10-9 + 59887-91-1 = 855-97-0
    反应条件:1.1 Reagents: Oxygen Catalysts: 5-Nitro-1,10-Phenanthroline,Palladium Trifluoroacetate Solvents: Dimethyl Sulfoxide; 100 °C
    标题:Identification And Structure Activity Relationship Of Novel Flavone Derivatives That Inhibit The Production Of Nitric Oxide And Pge2 In Lps-Induced Raw 264.7 Cells
    作者:An,Ji-Young; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2017 卷标:27(11) 页码:2613-2616]

    = 855-97-0
    反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol
    标题:An Environmentally Benign Synthesis Of Aurones And Flavones From 2'-Acetoxychalcones Using N-Tetrabutylammonium Tribromide
    作者:Bose,Gopal; Et Al
    参考文献:Tetrahedron Letters 日期:2001 卷标:42(50) 页码:8907-8909]

    90-24-4 = 855-97-0
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 20 H,Rt1.2 Reagents: Potassium Hydroxide Solvents: Pyridine; 10 Min,100 °C; 100 °C -> Rt1.3 Reagents: Acetic Acid; Neutralized,Rt1.4 Reagents: Sulfuric Acid Solvents: Acetic Acid; 10 Min,100 °C
    标题:Relationship Between Structure And Antiproliferative Activity Of Polymethoxyflavones Towards Hl60 Cells
    作者:Kawaii,Satoru; Et Al
    参考文献:Anticancer Research 日期:2012 卷标:32(12) 页码:5239-5244]

    1239-68-5 = 855-97-0 [标题:Reaction Conditions
    标题:Plants Of New Caledonia. Part 105. Bubbialine And Bubbialidine,Novel Alkaloids From Extracts Of Zygogynum Pauciflorum
    作者:Ahond,A.; Et Al
    参考文献:Journal Of Natural Products 日期:1990 卷标:53(4) 页码:875-81]

    1064710-43-5 = 855-97-0
    反应条件:1.1 Reagents: Cesium Carbonate Solvents: Acetone; 10 Min,Rt
    标题:Facile Access To Sterically Hindered Aryl Ketones Via Carbonylative Cross-Coupling: Application To The Total Synthesis Of Luteolin
    作者:O'Keefe,B. Michael; Et Al
    参考文献:Tetrahedron 日期:2011 卷标:67(24) 页码:4344-4351]

    114021-60-2 = 855-97-0
    反应条件:1.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 45 Min,130 - 140 °C
    标题:An Improved Synthesis Of Apigenin And Luteolin
    作者:Rambabu,A.; Et Al
    参考文献:Asian Journal Of Chemistry 日期:2016 卷标:28(5) 页码:1139-1143]

    114021-60-2 = 855-97-0
    反应条件:1.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 5 H,120 °C1.2 Reagents: Sodium Bisulfite Solvents: Water
    标题:Modified Syntheses Of The Dietary Flavonoid Luteolin
    作者:Wang,Qian; Et Al
    参考文献:Journal Of Chemical Research 日期:2015 卷标:39(9) 页码:550-552]

    10496-67-0 = 855-97-0
    反应条件:1.1 Reagents: Dimethyl Sulfoxide Solvents: Dimethyl Sulfoxide; Rt -> 150 °C1.2 Catalysts: Iodine; 30 Min,150 °C; 150 °C -> Rt1.3 Reagents: Potassium Pyrosulfite Solvents: Water; Rt
    标题:Oxidative Dimerisation Of Isoflavones: Synthesis Of Kudzuisoflavone A And Related Compounds
    作者:Deodhar,Mandar; Et Al
    参考文献:Australian Journal Of Chemistry 日期:2012 卷标:65(10) 页码:1377-1383]

    491-70-3 = 855-97-0
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; 10 H,Reflux
    标题:Synthesis,Characterization,Anti-Inflammatory And Anti-Proliferative Activity Against Mcf-7 Cells Of O-Alkyl And O-Acyl Flavonoid Derivatives
    作者:Hoang,T. Kim-Dung; Et Al
    参考文献:Bioorganic Chemistry 日期:2015 卷标:63 页码:45-52]

    491-70-3 = 855-97-0
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; Rt; Rt -> Reflux; 24 H,Reflux
    标题:Discovery Of Novel Apigenin-Piperazine Hybrids As Potent And Selective Poly (Adp-Ribose) Polymerase-1 (Parp-1) Inhibitors For The Treatment Of Cancer
    作者:Long,Huan; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2021 卷标:64(16) 页码:12089-12108]

    71847-57-9 = 855-97-0
    反应条件:1.1 Reagents: Sulfuric Acid Solvents: Acetic Acid; 1 H,110 °C
    标题:Novel Synthesised Flavone Derivatives Provide Significant Insight Into The Structural Features Required For Enhanced Anti-Proliferative Activity
    作者:Ravishankar,Divyashree; Et Al
    参考文献:Rsc Advances 日期:2016 卷标:6(69) 页码:64544-64556]

    122775-35-3 + 67837-36-9 = 855-97-0
    反应条件:1.1 Reagents: Cesium Carbonate Catalysts: Tricyclohexylphosphine,Tris(Dibenzylideneacetone)Dipalladium Solvents: 1,4-Dioxane; Rt -> 100 °C; 22 H,100 °C
    标题:Flavonoid-Based Inhibitors Of The Phi-Class Glutathione Transferase From Black-Grass To Combat Multiple Herbicide Resistance
    作者:Schwarz,Maria; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2021 卷标:19(42) 页码:9211-9222]

    122775-35-3 + 67837-36-9 = 855-97-0
    反应条件:1.1 Reagents: Potassium Carbonate Catalysts: Tetrakis(Triphenylphosphine)Palladium Solvents: 1,4-Dioxane; 18 H,Reflux
    标题:Divergent Approach To Flavones And Aurones Via Dihaloacrylic Acids. Unexpected Dependence On The Halogen Atom
    作者:Kraus,George A.; Et Al
    参考文献:Organic Letters 日期:2010 卷标:12(22) 页码:5278-5280]

    90-24-4 = 855-97-0
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 24 H,Rt1.2 Reagents: Sodium Tert-Butoxide Solvents: Dimethylformamide; 1 H,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water; Acidified,Rt2.1 Catalysts: Diethyl N-[(Trifluoromethyl)Sulfonyl]Phosphoramidate Solvents: Methanol
    标题:Mild And Efficient Organocatalytic Method For The Synthesis Of Flavones
    作者:Stanek,Filip; Et Al
    参考文献:Tetrahedron Letters 日期:2016 卷标:57(34) 页码:3841-3843]

    3187-19-7 + 4302-52-7 = 855-97-0
    反应条件:1.1 Reagents: Diphenyl Sulfide,Potassium Carbonate Catalysts: Acridinium,10-Methyl-9-(2,4,6-Trimethylphenyl)-,Perchlorate (1:1) Solvents: Dimethyl Sulfoxide,Water; 25 °C
    标题:Visible Light-Induced Deoxygenation/cyclization Of Salicylic Acid Derivatives And Aryl Acetylene For The Synthesis Of Flavonoids
    作者:Fan,Xiaodong; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2022 卷标:58(43) 页码:6348-6351]

    = 855-97-0
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; 0.5 H,65 °C1.2 65 °C; 6 H,65 °C
    标题:Synthesis And Biological Activity Of Novel Flavonoids Galactoconjugates
    作者:Lou,Dinghui; Et Al
    参考文献:Youji Huaxue 日期:2013 卷标:33(3) 页码:535-541]

    = 855-97-0
    反应条件:1.1 Catalysts: Potassium Carbonate Solvents: Acetone; 40 - 45 °C
    标题:Synthesis,In Silico And In Vitro Evaluation Of Some Flavone Derivatives For Acetylcholinesterase And Bace-1 Inhibitory Activity
    作者:Tran,Thai-Son; Et Al
    参考文献:Molecules 日期:2020 卷标:25(18)]

    = 855-97-0 [标题:Reaction Conditions
    标题:Chemical Constituents Of Nephrolepis Tuberosa
    作者:Banerjee,Jayanta; Et Al
    参考文献:Journal Of The Indian Chemical Society 日期:1988 卷标:65(12) 页码:881-2]

    110865-03-7 + 139-85-5 = 855-97-0
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Methanol; 18 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 5,Cooled2.1 Reagents: Potassium Carbonate Solvents: Acetone; Rt; Rt -> Reflux; 24 H,Reflux
    标题:Discovery Of Novel Apigenin-Piperazine Hybrids As Potent And Selective Poly (Adp-Ribose) Polymerase-1 (Parp-1) Inhibitors For The Treatment Of Cancer
    作者:Long,Huan; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2021 卷标:64(16) 页码:12089-12108]

    90-24-4 + 120-14-9 = 855-97-0
    反应条件:1.1 Catalysts: Potassium Hydroxide Solvents: Methanol; 72 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 52.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 1 - 3 H,135 °C; 135 °C -> Rt2.2 Reagents: Sodium Thiosulfate Solvents: Water
    标题:Computer-Aided Identification,Synthesis,And Biological Evaluation Of Dna Polymerase η Inhibitors For The Treatment Of Cancer
    作者:Munafo,Federico; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2023 卷标:248]

    90-24-4 + 120-14-9 = 855-97-0
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 2 H,0 °C2.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 12 H,110 °C
    标题:Anti-Melanogenic Properties Of Velutin And Its Analogs
    作者:Jung,Se-Hui; Et Al
    参考文献:Molecules 日期:2021 卷标:26(10)]

    90-24-4 + 120-14-9 = 855-97-0
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; > 1 Min,0 °C1.2 Overnight,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 1,Rt2.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; Reflux2.2 Reagents: Sodium Thiosulfate Solvents: Water
    标题:Synthesis Of Benzopyran-Fused Flavone Derivatives Via Microwave-Assisted Intramolecular C-H Activation
    作者:Sipos,Zoltan; Et Al
    参考文献:Synthesis 日期:2018 卷标:50(8) 页码:1610-1620
📜花旗松素置于间苯三酚体系中,用 甲醇,乙醚,乙酸乙酯 作为反应溶剂,化学反应 53.0H,反应生成 3,4,5,7-四甲氧基黄酮
参考文献:α-酮醇的光化学脱氧:二氢黄酮醇-黄酮酮转化
标题:α-酮醇的光化学脱氧:二氢黄酮醇-黄酮酮转化
摘要:在无水乙酸乙酯中辐照光学纯的2,3-反-3-羟基黄酮类化合物直接导致游离酚类黄烷酮类似物的完全保留在c(2)的配置.类似地,它们的甲基醚得到相应的黄烷酮和黄酮.该反应代表在clemmensen条件下还原的光化学当量.
DOI:10.1039/p19800001003

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主要参考文献


1: Bawazeer MA, Theoharides TC. IL-33 stimulates human mast cell release of CCL5 and CCL2 via MAPK and NF-κB, inhibited by methoxyluteolin. Eur J Pharmacol. 2019 Dec 15;865:172760. doi: 10.1016/j.ejphar.2019.172760. Epub 2019 Oct 26. 115(40):E9381-E9390. doi: 10.1073/pnas.1810133115. Epub 2018 Sep 19.
3: Patel AB, Theoharides TC. Methoxyluteolin Inhibits Neuropeptide-stimulated Proinflammatory Mediator Release via mTOR Activation from Human Mast Cells. J Pharmacol Exp Ther. 2017 Jun;361(3):462-471. doi: 10.1124/jpet.117.240564. Epub 2017 Apr 12. 113(45):E7138. doi: 10.1073/pnas.1616587113. Epub 2016 Nov 1. Erratum for: Proc Natl Acad Sci U S A. 2016 Nov 8;113(45):E7049-E7058.
5: Patel AB, Tsilioni I, Leeman SE, Theoharides TC. Neurotensin stimulates sortilin and mTOR in human microglia inhibitable by methoxyluteolin, a potential therapeutic target for autism. Proc Natl Acad Sci U S A. 2016 Nov 8;113(45):E7049-E7058. doi: 10.1073/pnas.1604992113. Epub 2016 Sep 23. Erratum in: Proc Natl Acad Sci U S A. 2016 Nov 1;:

合成参考文献


摘要:Dong, X.; Liu , H., Science of Synthesis Knowledge Updates, (2019) 3, .
摘要:Dong, X.; Liu, H., Science of Synthesis Knowledge Updates, (2019) 3, 2.
摘要:Sellars, J. D., Science of Synthesis Knowledge Updates, (2014) 1, 425.
参考文献:10.1016/s0006-291x(02)00755-6
摘要:Choi CH, Sun KH, An CS, Yoo JC, Hahm KS, Lee IH, Sohng JK, Kim YC. Reversal of P-glycoprotein-mediated multidrug resistance by 5,6,7,3',4'-pentamethoxyflavone (Sinensetin). Biochem Biophys Res Commun. 2002 Jul 26;295(4):832–40. doi: 10.1016/s0006-291x(02)00755-6.
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