CAS: 92-61-5; 7-Hydroxy-6-Methoxy-2H-Chromen-2-One

该化合物是一种天然生成的科马林衍生物,具有显著的生物活动,包括抗炎,抗氧化剂和抗微生物特性. 由于其能够调节细胞过程,它被广泛用于制药和化妆研究. 它的高度纯度和稳定性使它成为分析和药理研究的可靠参考标准.

结构式图片

相似化合物

305-01-1 574-84-5 13252-84-1

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号56795-51-8 乙酸东莨菪素酯 | CAS号305-01-1 秦皮乙素 | CAS号74-88-4 碘甲烷 | CAS号73490-50-3 Z-4,5-dimethoxy... | CAS号531-44-2 东莨菪甙； 东莨菪苷 | CAS号51061-83-7 2,4-二羟基-5-甲氧基苯甲醛 | CAS号1099-45-2 乙基(三苯基膦)乙酸酯 | CAS号4460-86-0 2,4,5-三甲氧基苯甲醛 | CAS号531-44-2 东莨菪甙； 东莨菪苷 | CAS号574-84-5 秦皮素 | CAS号305-01-1 秦皮乙素 | CAS号74-88-4 碘甲烷 | CAS号120-08-1 滨蒿內酯 | CAS号67370-98-3 2,4-dihydroxy-5... | CAS号78876-49-0 7-[(3,3-dimethy... | CAS号90843-91-7 7-hydroxy-6-met... | CAS号6054-10-0 布拉易林

合成工艺路线路线简述

  • 6100-60-3 + 623-47-2 = 92-61-5
    反应条件:1.1 Catalysts: Trifluoromethanesulfonic Acid Solvents: Toluene; Rt -> 80 °C; 3 H,80 °C; 80 °C -> Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water; Ph 6 - 8,Rt
    标题:Scopoletin Manufacturing Method
    参考文献:Korea]

    141-82-2 + 51061-83-7 = 92-61-5
    反应条件:1.1 Solvents: N,N-Dimethylaniline; Rt -> Reflux; 4 H,Reflux
    标题:Method For Preparing Scopoletin From 2,4-Dihydroxy-5-Methoxy Benzaldehyde
    参考文献:China]

    853928-01-5 = 92-61-5
    反应条件:1.1 Solvents: Ethylene Glycol,Pyridine; 3.5 H,Reflux; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 4,Cooled
    标题:Synthesis And Biological Evaluation Of Scopoletin Derivatives
    作者:Cai,Xueting; Yang,Jie; Zhou,Jinpei; Lu,Wuguang; Hu,Chunping; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2013 卷标:21(1) 页码:84-92]

    853928-01-5 = 92-61-5
    反应条件:1.1 Reagents: Pyridine Solvents: Ethylene Glycol; 3.5 H,Reflux
    标题:Preparation Of Scopoletin Derivatives As Antitumor Agents
    参考文献:China]

    853928-01-5 = 92-61-5
    反应条件:1.1 Solvents: Ethylene Glycol,Pyridine; 3.5 H,Reflux; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 4
    标题:Synthesis And In Vitro Antitumor Activity Of Novel Scopoletin Derivatives
    作者:Liu,Wukun; Hua,Jie; Zhou,Jinpei; Zhang,Huibin; Zhu,Haiyang; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2012 卷标:22(15) 页码:5008-5012]

    853928-01-5 = 92-61-5
    反应条件:1.1 Reagents: Pyridine Solvents: Ethylene Glycol; 3.5 H,Reflux1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 4,Cooled
    标题:Synthesis And Antitumor Activity Of Scopoletin Derivatives
    作者:Zhou,Jinpei; Wang,Lei; Wei,Lijuan; Zheng,Yu; Zhang,Huibin; Et Al
    参考文献:Letters In Drug Design & Discovery 日期:2012 卷标:9(4) 页码:397-401]

    120-08-1 = 92-61-5
    反应条件:1.1 Reagents: Lithium Chloride Solvents: Dimethylformamide; 30 Min
    标题:Synthesis Of Scopoletin With Assisted Microwave Irradiation
    作者:Fang,Zhuan; He,Guang-Li; He,Ling
    参考文献:Huaxi Yaoxue Zazhi 日期:2007 卷标:22(3) 页码:302-303]

    1279586-71-8 = 92-61-5
    反应条件:1.1 Reagents: Zinc Chloride Solvents: 1,4-Dioxane; 8 D,100 °C
    标题:New Approach For The Construction Of The Coumarin Frame And Application In The Total Synthesis Of Natural Products
    作者:Jerezano,Alberto; Jimenez,Fabiola; Cruz,Maria Del Carmen; Montiel,Luisa E.; Delgado,Francisco; Et Al
    参考文献:Helvetica Chimica Acta 日期:2011 卷标:94(2) 页码:185-198]

    6100-60-3 + 34780-29-5 = 92-61-5
    反应条件:1.1 Solvents: Ethyl Acetate
    标题:An Improved And Large Scale Synthesis Of The Natural Coumarin Scopoletin
    作者:Hauer,Hermann; Ritter,Thomas; Grotemeier,Gregor
    参考文献:Archiv Der Pharmazie (Weinheim 日期:1995 卷标:328(10) 页码:737-8]

    608536-52-3 = 92-61-5
    反应条件:1.1 Catalysts: Sodium Bisulfate (Silica-Supported); 48 H,120 °C1.2 Solvents: Dichloromethane; 1.5 H,Rt
    标题:Simple,Efficient,And Selective Deprotection Of Phenolic Methoxymethyl Ethers Using Silica-Supported Sodium Hydrogen Sulfate As A Heterogeneous Catalyst
    作者:Ramesh,C.; Ravindranath,N.; Das,Biswanath
    参考文献:Journal Of Organic Chemistry 日期:2003 卷标:68(18) 页码:7101-7103]

    305-01-1 = 92-61-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0.5 H,0 °C1.2 0 - 5 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; 0 - 5 °C
    标题:Synthesis And Structure-Activity Relationship Of Coumarins As Potent Mcl-1 Inhibitors For Cancer Treatment
    作者:Xia,Yang-Liu; Wang,Jing-Jing; Li,Shi-Yang; Liu,Yong; Gonzalez,Frank J.; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2021 卷标:29]

    853928-01-5 = 92-61-5
    反应条件:1.1 Reagents: Pyridine Solvents: Ethylene Glycol; 3.5 H,Reflux; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 4
    标题:Gastroprotective Activity Of Synthetic Coumarins: Role Of Endogenous Prostaglandins,Nitric Oxide,Non-Protein Sulfhydryls And Vanilloid Receptors
    作者:Sepulveda,Beatriz; Quispe,Cristina; Simirgiotis,Mario; Torres-Benitez,Alfredo; Reyes-Ortiz,Johanna; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2016 卷标:26(23) 页码:5732-5735]

    305-01-1 = 92-61-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0.5 H,0 °C1.2 0.3 H,0 - 5 °C1.3 Reagents: Water; Cooled1.4 Reagents: Hydrochloric Acid Solvents: Water; Acidified
    标题:An Expedient Method For Regioselective Methylation Of Catechol Coumarins
    作者:Lu,Junxia; Wang,Ping; Hou,Jie; Zou,Liwei; Cui,Pan; Et Al
    参考文献:Chemical Research In Chinese Universities 日期:2016 卷标:32(5) 页码:786-791]

    1099-45-2 + 51061-83-7 = 92-61-5
    反应条件:1.1 Solvents: N,N-Diethylaniline; 15 Min,Reflux
    标题:Total Synthesis Of Six 3,4-Unsubstituted Coumarins
    作者:Gao,Wenqing; Li,Qingyong; Chen,Jian; Wang,Zhichao; Hua,Changlong
    参考文献:Molecules 日期:2013 卷标:18(12) 页码:15613-15623]

    853928-01-5 = 92-61-5
    反应条件:1.1 Solvents: Pyridine; 3.5 H,Reflux; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:Design,Synthesis And Cytotoxic Activities Of Scopoletin-Isoxazole And Scopoletin-Pyrazole Hybrids
    作者:Shi,Wei; Hu,Jinglin; Bao,Na; Li,Dongang; Chen,Li; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2017 卷标:27(2) 页码:147-151]

    120-08-1 = 92-61-5
    反应条件:1.1 Reagents: Lithium Chloride Solvents: Dimethylformamide; 28 Min,160 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 0 °C
    标题:Lithium Chloride-Catalyzed Selective Demethylation Of Aryl Methyl Ethers Under Microwave Irradiation
    作者:Fang,Zhuan; Zhou,Guo-Chuan; Zheng,Shi-Long; He,Guang-Li; Li,Ju-Lian; Et Al
    参考文献:Journal Of Molecular Catalysis A: Chemical 日期:2007 卷标:274(1-2) 页码:16-23]

    10601-80-6 + 6100-60-3 = 92-61-5
    反应条件:1.1 Reagents: Phosphoric Acid
    标题:New Syntheses In The Coumarin Series
    作者:Crosby,Donald G.; Berthold,Robert V.
    参考文献:Journal Of Organic Chemistry 日期:1962 卷标:27 页码:3083-5]

    1099-45-2 + 51061-83-7 = 92-61-5
    反应条件:1.1 Solvents: N,N-Diethylaniline; 12 H,Rt -> Reflux
    标题:First Total Synthesis Of Artekeiskeanol A,C And Altissimacoumarin D
    作者:Talakokkula,Anil; Baikadi,Karunakar; Narsaiah,A. Venkat
    参考文献:Synopen 日期:2019 卷标:3(2) 页码:49-54]

    853928-01-5 = 92-61-5
    反应条件:1.1 Reagents: Pyridine Solvents: Ethylene Glycol; 50 Min,> 110 °C; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 5
    标题:Synthesis And Acaricidal Activities Of Scopoletin Phenolic Ether Derivatives: Qsar,Molecular Docking Study And In Silico Adme Predictions
    作者:Luo,Jinxiang; Lai,Ting; Guo,Tao; Chen,Fei; Zhang,Linli; Et Al
    参考文献:Molecules 日期:2018 卷标:23(5)]

    4460-86-0 + 1099-45-2 = 92-61-5
    反应条件:1.1 Reagents: Aluminum Chloride Solvents: Dichloromethane; Rt; 23 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Cooled1.3 Solvents: N,N-Diethylaniline; 5 H,180 °C; 180 °C -> Rt1.4 Reagents: Hydrochloric Acid Solvents: Water
    标题:Scopoletin Derivative,Its Application In Preparation Of Anticoagulant Drug For Treatment Of Venous Thrombosis Disease,And Its Preparation
    参考文献:China
📜6-Methoxy-7-Methoxymethoxy-Chromen-2-One置于sodium Hydrogen Sulfate,Silica Gel体系中,用 二氯甲烷 作为反应溶剂,化学反应 1.5H,以91%的收率获得产物东莨菪内酯
参考文献:使用二氧化硅负载的硫酸氢钠作为多相催化剂,对酚类甲氧基甲基醚进行简单,有效和选择性的脱保护.
标题:使用二氧化硅负载的硫酸氢钠作为多相催化剂,对酚类甲氧基甲基醚进行简单,有效和选择性的脱保护.
摘要:已经开发出一种简单有效的方法,以二氧化硅为载体的硫酸氢钠为非均相催化剂,对苯酚甲氧基甲基(mom)醚进行化学选择性脱保护.该转化在室温下发生,并且脱保护的苯酚的收率非常好.该方法适用于多功能生物活性天然产物的酚mom醚的脱保护.
DOI:10.1021/jo030088+

海关参考信息

专利信息


专利号:US-8143308-B2
优先权日:2005-04-28
标题 :Synthesis of oligo/poly(catechins) and methods of use
发明人：BRUNO FERDINANDO F; KUMAR JAYANT; NAGARAJAN SUBHALAKSHMI; BRAUNHUT SUSAN J; NAGARAJAN RAMASWAMY; SAMUELSON LYNNE A; MCINTOSH DONNA; FOLEY KLAUDIA
权利人:BRUNO FERDINANDO F; KUMAR JAYANT; NAGARAJAN SUBHALAKSHMI; BRAUNHUT SUSAN J; NAGARAJAN RAMASWAMY; SAMUELSON LYNNE A; MCINTOSH DONNA; FOLEY KLAUDIA; UNIV MASSACHUSETTS LOWELL; US ARMY
摘要:A method for synthesizing a biocompatible, water-soluble oligo/polyflavanoid, includes polymerizing an optionally substituted flavanoid with a polymerization agent in the presence of a biocompatible polymerization solubilizer, thereby producing the biocompatible, soluble oligo/polyflavanoid. Also included is a biocompatible, soluble, oligo/polyflavanoid or a pharmaceutically acceptable salt, solvate, or complex thereof. Also included are methods of treating a subject for cancer, cardiac damage, viral infection, and obesity.

专利号:WO-2024259172-A1
优先权日:2023-06-14
标题 :Improved synthesis of cannabinoid glycoside compounds
发明人：HUSSAIN SYED
权利人:TRAIT BIOSCIENCES INC
摘要:The present invention relates generally to the identification novel UDP -glucosyltransferases enzymes having specific activity towards cannabinoid compounds. The present invention further relates generally to the use of novel UGT enzymes having specific activity towards cannabinoid compounds to generate water-soluble cannabinoid glycoside compounds.

专利号:WO-2023156270-A1
优先权日:2022-02-18
标题:Coumarin synthesis and uses thereof
发明人：CONRATH UWE; LANGENBACH CASPAR; BEYER SEBASTIAN FELIX; SCHWINGES PATRICK; SCHULTHEISS HOLGER; BEESLEY ALEXANDER; LINKE CEDRIC
权利人:BASF SE; RWTH AACHEN
摘要:The present invention relates to genes, materials and methods for coumarin synthesis and the application thereof for improving plant health, preferably against infection by phythopathogenic microorganisms, and/or for improving plant health against coumarin-induced adverse effects on plant health. Furthermore, the invention pertains to methods and uses of such genes and mate- rials for creating correspondingly beneficial plant cells, plant parts and whole plants, and relates to products obtained from such plants or plant parts.

专利号:US-6337095-B1
优先权日:2000-03-30
标题 :Process for the isolation of compound scopoletin useful as nitric oxide synthesis inhibitor
发明人：JAIN DHARAM CHAND; PANT NEERJA; GUPTA MADAN MOHAN; BHAKUNI RAJENDRA SINGH; VERMA RAM KISHOR; TANDON SUDEEP; GUPTA SHIV KUMAR; TEWARI AMIT; KAHOL ATUL PRAKASH; KUMAR SUSHIL
权利人:COUNCIL SCIENT IND RES
摘要:The invention relates to a process for the isolation of compound scopoletin which is used as nitric oxide synthesis inhibitor from Artemisia annua and other plant families, said process comprising extraction of dried powdered material of different plant parts with an aqueous acetonitrite solvent in the ratio of 1:5 for 6 to 8 hrs., concentration of the extracted solvent upto 30% of its original extract under vacuum, partitioning the concentrated extract with halogenated solvent to transfer scopoletin in the non-polar halogenated solvent, drying halogenated solvent over anhydrous sodium sulphate and evaporating the solvent, crystallizing the residues in methanol and filtering the crystals, concentrating the filtrate and chromatographed on silica gel, eluting scopoletin in chloroform methanol mixture; and crystallization of the fractions containing the scopoletin to get the pure scopoletin compound.

专利号:US-2009170928-A1
优先权日:2005-04-28
标题:Synthesis of oligo/poly(catechins) and methods of use

专利号:US-2018105546-A1
优先权日:2011-06-14
标题:Methods for Chemical Synthesis of Biologically Active Compounds Using Supramolecular Protective Groups and Novel Compounds Obtainable Thereby

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主要参考文献


1: Datta S, Paul S, Ballabh L, Mitra A. Histochemical and molecular analyses reveal an insight into the scent volatiles synthesis and emission in ephemeral flowers of Murraya paniculata (L.) Jack. Planta. 2024 Oct 18;260(5):119. doi: 10.1007/s00425-024-04552-6.
15:1423480. doi: 10.3389/fphar.2024.1423480.
4: Elbakush AM, Trunschke O, Shafeeq S, Römling U, Gomelsky M. Maple compounds prevent biofilm formation in Listeria monocytogenes via sortase inhibition. Front Microbiol. 2024 Sep 16;15:1436476. doi: 10.3389/fmicb.2024.1436476.

合成参考文献


参考文献:10.1080/10286020.2011.586343
摘要:Saeed S, Shah S, Mehmood R, Malik A. Paniculacin, a new coumarin derivative fromMurraya paniculata. Journal of Asian Natural Products Research. 2011 Aug;13(8):724–7. doi: 10.1080/10286020.2011.586343.
参考文献:10.1186/1471-2164-12-370
摘要:Bajgain P, Richardson BA, Price JC, Cronn RC, Udall JA. Transcriptome characterization and polymorphism detection between subspecies of big sagebrush (Artemisia tridentata). BMC Genomics. 2011 Jul 18;12():370.
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