CAS: 973-67-1; 5,6,7-Trimethoxy-2-Phenyl-4H-Chromen-4-One

该化合物是属于五氯素类的合成有机化合物,特别是苯丙胺衍生物;这种化合物具有苯并呋喃核心结构,其特点是有苯并呋喃和苯丙胺环,代之以5,6,7个位置的三个甲氧组,以及2个位置的一个苯基组;这些替代物有助于其独特的化学特性,包括其生物活动的潜力;甲基氧基组的存在增强了其脂性,这可能影响其与生物膜及其总体生物利用率的相互作用;此外,这种化合物经常因其抗氧化剂,抗炎和抗癌特性而研究,使其对药用化学和药理学感兴趣;化合物的溶解性,稳定性和再活性可因环境条件而变化,例如PH和温度,这些是其应用和研究中的重要考虑因素.

结构式图片

物理性质

MSDS等安全信息

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C&L通报

上下游产品

7-羟基-5,6-二甲氧基-2-苯基色烯-4-酮 7-Hydroxy-5,6-Dimethoxy-2-Phenyl-4H-1-Benzopyran-4-One 04/05/2035
6-羟基-5,7-二甲氧基-2-苯基色烯-4-酮 6-Hydroxy-5,7-Dimethoxyflavone 119892-40-9
千层纸素a Oroxylin A 480-11-5
柯因二甲醚 Dimethyl-Chrysin 21392-57-4
黄芩素 5,6,7-Trihydroxy-2-Phenyl-4H-1-Benzopyran-4-One 491-67-8
黄芩苷 Baicalin 21967-41-9
4-Hydroxy-5,6,7-Trimethoxycoumarin 68061-76-7

合成工艺路线路线简述

  • 491-67-8 = 973-67-1
    反应条件:1.1 Reagents: Pyridine,Potassium Carbonate Solvents: Acetone; 8 H,60 °C
    标题:Synthesis Of Ring A-Modified Baicalein Derivatives
    作者:Wang,Jun-Fei; Ding,Ning; Zhang,Wei; Wang,Peng; Li,Ying-Xia
    参考文献:Helvetica Chimica Acta 日期:2011 卷标:94(12) 页码:2221-2230]

    74064-14-5 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 2.5 H,100 °C
    标题:Total Synthesis Of Baicalein
    作者:Chen,Duo-Zhi; Yang,Jian; Yang,Bo; Wu,Yuan-Shuang; Wu,Ting
    参考文献:Journal Of Asian Natural Products Research 日期:2010 卷标:12(2) 页码:124-128]

    74064-14-5 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 2 H,Reflux1.2 Solvents: Water
    标题:Methods Of Synthesizing Flavonoids And Chalcones
    参考文献:United States]

    74064-14-5 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; Rt -> 110 °C; 4 H,110 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; 1 H,110 °C
    标题:Method For Preparing Baicalein From 3,4,5-Trimethoxyphenol
    参考文献:China]

    74064-14-5 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide
    标题:4'-Bromo-5,6,7-Trimethoxyflavone Represses Lipopolysaccharide-Induced Inos And Cox-2 Expressions By Suppressing The Nf-Kb Signaling Pathway In Raw 264.7 Macrophages
    作者:Kim,Dong Han; Yun,Chang Hyeon; Kim,Min Hwan; Naveen Kumar,Ch.; Yun,Bo Hee; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2012 卷标:22(1) 页码:700-705]

    74064-14-5 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 2 H,100 °C
    标题:Activities Of Wogonin Analogs And Other Flavones Against Flavobacterium Columnare
    作者:Tan,Cheng-Xia; Schrader,Kevin K.; Khan,Ikhlas A.; Rimando,Agnes M.
    参考文献:Chemistry & Biodiversity 日期:2015 卷标:12(2) 页码:259-272]

    98-80-6 + 1255860-62-8 = 973-67-1
    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.; Gupta,Vinayak
    参考文献:Organic Letters 日期:2010 卷标:12(22) 页码:5278-5280]

    18107-18-1 + 491-67-8 = 973-67-1
    反应条件:1.1 Solvents: Methanol,Tetrahydrofuran,Hexane; 36 H,Rt
    标题:Preparation Of A Ring Alkylated Baicalein Analogs With Anti-P-Glycoprotein Activity
    参考文献:World Intellectual Property Organization]

    18107-18-1 + 491-67-8 = 973-67-1
    反应条件:1.1 Solvents: Methanol,Tetrahydrofuran,Hexane; 36 H,Rt
    标题:Increased Anti-P-Glycoprotein Activity Of Baicalein By Alkylation On The A Ring
    作者:Lee,Yashang; Yeo,Hosup; Liu,Shwu-Huey; Jiang,Zaoli; Savizky,Ruben M.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2004 卷标:47(22) 页码:5555-5566]

    74064-14-5 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 100 °C
    标题:Oroxylin A Analogs Exhibited Strong Inhibitory Activities Against Inos-Mediated Nitric Oxide (No) Production
    作者:Pham,Tuan-Ahn. N.; Che,Haiyan; Phan,Phuong-Thuy T.; Lee,Jae-Won; Kim,Sung-Soo; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2012 卷标:22(7) 页码:2534-2535]

    491-67-8 = 973-67-1
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; Overnight,Reflux
    标题:Synthesis And Evaluation Of Selenoflavones That Have Potential Neuroprotective Effects
    作者:Choi,Yong-Sung; Kim,Yoon-Jung; Lee,Ju Yeun; Lee,Jinu; Jeong,Jin-Hyun
    参考文献:Heterocycles 日期:2014 卷标:89(12) 页码:2794-2805]

    74064-14-5 = 973-67-1
    反应条件:1.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 2 H,Rt -> Reflux
    标题:Synthesis And Anti-Aggregatory Of Baicalein Derivatives Functionalized On The B-Ring
    作者:Wang,Jing; Liu,Xiang; Dong,Baoping
    参考文献:Aiche Annual Meeting 日期:2011 卷标:(2011)]

    70185-52-3 = 973-67-1
    反应条件:1.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 2 H,Reflux1.2 Reagents: Water; Cooled
    标题:Synthesis And Anticancer Activities Of 5,6,7-Trimethylbaicalein Derivatives
    作者:Liao,Hua-Lin; Hu,Ming-Kuan
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2004 卷标:52(10) 页码:1162-1165]

    70185-52-3 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 3 - 10 H,Reflux
    标题:Synthesis Of 5,6,7-Trimethoxyflavone As A Key Intermediate For The Preparation Of Baicalein
    作者:Huang,Wen-Hsin; Yang,Ching-Huey; Chien,Pei-Yu; Lee,An-Rong
    参考文献:Chinese Pharmaceutical Journal (Taipei 日期:2003 卷标:55(2) 页码:101-107]

    70185-52-3 = 973-67-1
    反应条件:1.1 Reagents: Iodine Solvents: Dimethyl Sulfoxide; 2 H,Reflux1.2 Solvents: Water
    标题:Novel Synthesis Of Flavonoids Of Scutellaria Baicalensis Georgi
    作者:Huang,Wen-Hsin; Chien,Pei-Yu; Yang,Ching-Huey; Lee,An-Rong
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2003 卷标:51(3) 页码:339-340]

    70185-52-3 = 973-67-1
    反应条件:1.1 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 2 H,Reflux
    标题:Fine Tuning Of A Reported Synthetic Route For Biologically Active Flavonoid,Baicalein
    作者:Kim,Sanghee; Sohn,Dae Won; Kim,Youn Chul; Kim,Soon-Ai; Lee,Sang Kook; Et Al
    参考文献:Archives Of Pharmacal Research 日期:2007 卷标:30(1) 页码:18-21]

    491-67-8 = 973-67-1
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; 8 H,Reflux
    标题:α-Glucosidase Inhibition Of 6-Hydroxyflavones. Part 3: Synthesis And Evaluation Of 2,3,4-Trihydroxybenzoyl-Containing Flavonoid Analogs And 6-Aminoflavones As α-Glucosidase Inhibitors
    作者:Gao,Hong; Kawabata,Jun
    参考文献:Bioorganic & Medicinal Chemistry 日期:2005 卷标:13(5) 页码:1661-1671]

    102-92-1 + 642-71-7 = 973-67-1
    反应条件:1.1 Reagents: Oxalyl Chloride Catalysts: Dimethylformamide Solvents: Dichloromethane; 0 °C; 5 Min,0 °C; 60 Min,Rt1.2 Reagents: Boron Trifluoride Etherate; 15 Min,Reflux1.3 Reagents: Water; Cooled1.4 Catalysts: Iodine Solvents: Dimethyl Sulfoxide; 2 H,Reflux
    标题:Synthesis Of Baicalein Derivatives As Potential Anti-Aggregatory And Anti-Inflammatory Agents
    作者:Huang,Wen-Hsin; Lee,An-Rong; Chien,Pei-Yu; Chou,Tz-Chong
    参考文献:Journal Of Pharmacy And Pharmacology 日期:2005 卷标:57(2) 页码:219-225]

    637-44-5 + 642-71-7 = 973-67-1
    反应条件:1.1 Reagents: Phosphorus Pentoxide,Trifluoromethanesulfonic Acid
    标题:Synthesis Of Highly Functionalized Flavones And Chromones Using Cycloacylation Reactions And C-3 Functionalization. A Total Synthesis Of Hormothamnione
    作者:Mcgarry,Lynda W.; Detty,Michael R.
    参考文献:Journal Of Organic Chemistry 日期:1990 卷标:55(14) 页码:4349-56]

    491-67-8 = 973-67-1
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Water; Reflux; 7 - 8 H,Reflux
    标题:Structural Modification Of The A-Ring Baicalein
    作者:Zhu,Zheng-Hui; Lei,Ze; Jiang,Ming-Zhong; Mu,Xiao-Yun; Fu,Zheng-Qi; Et Al
    参考文献:Yingyong Huaxue 日期:2010 卷标:27(9) 页码:1038-1041
📜3,4,5-三甲氧基苯酚置于三氟化硼乙醚,碘体系中,用 二甲基亚砜,甲苯 作为反应溶剂,化学反应 4.0H,反应生成 5,6,7三甲氧基黄酮
参考文献:沃戈宁类似物和其他黄酮对黄杆菌的活性.
标题:沃戈宁类似物和其他黄酮对黄杆菌的活性.
摘要:在我们不断探索发现天然产物和基于天然产物的化合物以控制引起黄channel鱼(ictalurus Punctatus)柱状菌病的细菌flavobacterium Columnare的过程中,我们合成了黄酮和查耳酮类似物,并评估了这些化合物以及使用快速生物测定法,从天然来源中提取黄酮类化合物,以抵抗其对柱状双歧杆菌的两种分离物(alm-00-173和biomed)的抗菌活性.黄酮类黄绿素(1A),5,7-二羟基-4'-甲氧基黄酮(11),异鼠李素(26),木犀草素(27)和生物素a(29)和查尔酮衍生物8B对f. Columnare具有较强的抗菌活性.基于最小抑制浓度(mic)的alm-00-173.黄酮类化合物1A,8,11,13(5,4'-二羟基-7-甲氧基黄酮),26,根据mic结果,29和29对f. Columnare Biomed表现出强大的抗菌活性.24小时50%抑制浓度(ic50)结果表明,27和29种化合物对f
DOI:10.1002/cbdv.201400181

海关参考信息

专利信息


专利号:US-10407401-B1
优先权日:2018-08-04
标题 :Process for synthesis of Oroxylin A
发明人：MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; HEMANTHA HOSAHALLI PRABHAKARA
权利人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; HEMANTHA HOSAHALLI PRABHAKARA; SAMI LABS LTD
摘要:Disclosed is a novel, simple, scalable and environment friendly process for the synthesis of Oroxylin A from Baicalin. Baicalin is esterified to obtain a methyl ester which is further selectively methylated to provide Oroxylin A glucuronide methyl ester which on de-glycosylation results in the formation of Oroxylin A.

专利号:US-2007232495-A1
优先权日:2006-03-24
标题:Compositions and methods to add value to plant products, increasing the commercial quality, resistance to external factors and polyphenol content thereof
发明人：NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
权利人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
摘要:The invention is related to compositions and methods that naturally protect plant tissues against ultraviolet radiation and temperature, thus giving protection against sunburn to plants, plant parts, fruits and/or flowers during their development. The invention is also related to compositions and methods to naturally improve the color of plants, plant parts, fruits and/or flowers by inducing the natural synthesis of flavonoids and anthocyanins present in plants. Likewise, the present invention is directed to improving the nutritional value of plants, plant parts, fruits and/or flowers by increasing the normal levels of polyphenolic compounds, especially flavonoids, present therein. Additionally, the present invention is related to compositions and methods that give more resistance to plants, plant parts, fruits and/or flowers against pathogens as bacteria and fungi. Finally, the present invention is related to plants, plant parts, fruits, flowers and/or propagating material treated with the compositions described in the present document.

专利号:CN-110498739-A
优先权日:2019-09-12
标题:A method of synthesis 6- hydroxyl -2,3,4- trimethoxy-alpha-chloro acetophenone

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主要参考文献

参考标题: Process For Synthesis Of Oroxylin A Procédé De Synthèse D'Oroxyline A
摘要:Disclosed Is A Novel, Simple, Scalable And Environment Friendly Process For The Synthesis Of Oroxylin A From Baicalin. Baicalm Is Esterified To Obtain A Methyl Ester Which Is Further Selectively Methylated To Provide Oroxylin A Gluciironide Methyl Ester Which On De- Glycosylation Results In The Formation Of Oroxylin A.

合成参考文献


摘要:Williams, A. C.; Camp, N., Science of Synthesis, (2003) 14, 478.
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