CAS: 939-19-5; 3-Hydroxy-2H-Chromen-2-One

该化合物是科马林家族的一个化学化合物,其特点是芳香结构,在科马林环的三处有一个氢氧化物组,该化合物一般是白色的黄色晶状固体,以其荧光特性著称,它可用于各种应用,包括作为生物化学实验中的荧光标志. 3-Hydroxycoumarin在有机溶剂中表现出中等溶解性,水溶性有限,这可能会影响其生物系统的行为.该化合物还因其潜在的药理特性,包括抗coagurant活动而得到承认,并因其在其他生物活性化合物合成中的作用而得到研究.此外,该化合物可产生各种化学反应,例如酯化和氧化,使其成为有机合成的多功能中间体.安全数据表明,尽管它可能构成某些健康风险,但适当的处理和使用准则可以减轻这些关切.

结构式图片

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779-30-6 3-乙酰氨基香豆素 | CAS号1635-31-0 3-氨基香豆素 | CAS号334022-78-5 2-hydroxy-3-(2-... | CAS号1473-60-5 N-salicylidene-... | CAS号90-02-8 水杨醛 | CAS号135-02-4 邻甲氧基苯甲醛 | CAS号782503-73-5 2-甲基-(4z)-(21-甲... | CAS号89-95-2 邻甲基苄醇 | CAS号90-02-8 水杨醛 | CAS号23891-02-3 3-prop-2-enoxyc... | CAS号2549-07-7 3-methoxycoumarin | CAS号135-02-4 邻甲氧基苯甲醛 | CAS号1635-31-0 3-氨基香豆素 | CAS号15185-05-4 4-苯基香豆素 | CAS号73844-55-0 3-hydroxy-4-(1-... | CAS号91787-19-8 3-phenoxychrome...

合成工艺路线路线简述

  • 合成目标产物 3-Hydroxycoumarin 主要起始原料 3-Aminocoumarin
  • 779-30-6 = 939-19-5
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 4 H,Reflux
    标题:Synthesis And Biological Evaluation Of Alkoxycoumarins As Novel Nematicidal Constituents
    作者:Takaishi,Kazuto; Izumi,Minoru; Baba,Naomichi; Kawazu,Kazuyoshi; Nakajima,Shuhei
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2008 卷标:18(20) 页码:5614-5617]

    543-24-8 + 90-02-8 = 939-19-5
    反应条件:1.1 Reagents: Sodium Acetate Solvents: Acetic Acid,Acetic Anhydride; Reflux1.2 Reagents: Hydrochloric Acid Solvents: Water; Reflux
    标题:New Efficient Synthesis Of Pyrido[2,3-C]- And Pyrido[3,2-C]Coumarin Derivatives
    作者:Pave,Gregoire; Chalard,Pierre; Viaud-Massuard,Marie-Claude; Troin,Yves; Guillaumet,Gerald
    参考文献:Synlett 日期:2003 卷标:(7) 页码:987-990]

    4732-72-3 = 939-19-5
    反应条件:1.1 Solvents: Diethyl Ether
    标题:Reactions Of Some Diazoalkanes With Isatin,N-Methylisatin,Coumarandione,And Thionaphthenequinone
    作者:Eistert,Bernd; Selzer,Herbert
    参考文献:Chemische Berichte 日期:1963 卷标:96 页码:1234-55]

    52900-70-6 = 939-19-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 2 - 3 H,Reflux1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:Inhibition Of Inos By Benzimidazole Derivatives: Synthesis,Docking,And Biological Evaluations
    作者:Minhas,Richa; Bansal,Yogita
    参考文献:Medicinal Chemistry (Sharjah 日期:2022 卷标:18(5) 页码:602-615]

    616-34-2 + 90-02-8 = 939-19-5
    反应条件:1.1 Reagents: Triethylamine1.2 Reagents: Sulfuric Acid Solvents: Water
    标题:Hydroxycoumarin Derivatives: Novel And Potent α-Glucosidase Inhibitors
    作者:Shen,Qiong; Shao,Jia-Liang; Peng,Quan; Zhang,Wan-Jin; Ma,Lin; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2010 卷标:53(23) 页码:8252-8259]

    1635-31-0 = 939-19-5
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water
    标题:Synthesis And Study Of Substituted Coumarins. A Facile Preparation Of D,L-O-Tyrosine
    作者:Kokotos,George; Tzougraki,Chrysa
    参考文献:Journal Of Heterocyclic Chemistry 日期:1986 卷标:23(1) 页码:87-92]

    779-30-6 = 939-19-5
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water
    标题:Synthesis Of O-Tyrosine And Related Phenolic Acids
    作者:Shaw,Kenneth N. F.; Mcmillan,Armand; Armstrong,Marvin D.
    参考文献:Journal Of Organic Chemistry 日期:1956 卷标:21 页码:601-4]

    = 939-19-5 [标题:Reaction Conditions
    标题:Design,Synthesis And Biological Evaluation Of Coumarin Alkylamines As Potent And Selective Dual Binding Site Inhibitors Of Acetylcholinesterase
    作者:Catto,Marco; Pisani,Leonardo; Leonetti,Francesco; Nicolotti,Orazio; Pesce,Paolo; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2013 卷标:21(1) 页码:146-152]

    = 939-19-5 [标题:Reaction Conditions
    标题:Product Class 4: Benzopyranones And Benzopyranthiones
    作者:Williams,A. C.; Camp,N.
    参考文献:Science Of Synthesis 日期:2003 卷标:14 页码:347-638]

    33567-53-2 = 939-19-5 + 334022-88-7 + 334022-89-8
    反应条件:1.1 Reagents: Boron Tribromide Solvents: Dichloromethane
    标题:Reaction Of Aryl-2-Hydroxypropenoic Derivatives With Boron Tribromide
    作者:Dupont,R.; Cotelle,P.
    参考文献:Tetrahedron Letters 日期:2001 卷标:42(4) 页码:597-600]

    779-30-6 = 939-19-5
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 5 H,Reflux
    标题:Novel Pharmaceutically Active Pyranochromene Compounds Useful As Antiviral Agents And Process Of Preparation Thereof
    参考文献:India]

    52900-70-6 = 939-19-5
    反应条件:1.1 Reagents: Sodium Solvents: Water; 2 H,Reflux
    标题:Synthesis Of Furano[2,3-C]/pyrrolo[2,3-C]Coumarins And Synthesis Of 1(H)-[1]Benzopyrano[3,4-B][1]Benzopyrano[3',4'-D]Furan-7(H)-Ones /1(H)-[1]Benzopyrano[3,4-B][1]Benzopyrano[3',4'-D]Pyrrole-7(H)-Ones
    作者:Pandya,Mahesh K.; Chhasatia,Mehulsinh R.; Vala,Nileshkumar D.; Parekh,Tapan H.
    参考文献:Journal Of Drug Delivery And Therapeutics 日期:2019 卷标:9 页码:32-42]

    2549-08-8 = 939-19-5
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Water1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:A Facile Synthesis Of 3-Acylaminocoumarins
    作者:Tripathy,Pradeep K.; Mukerjee,Arya K.
    参考文献:Indian Journal Of Chemistry 日期:1987 卷标:(1) 页码:61-2]

    207910-76-7 = 939-19-5
    反应条件:1.1 Reagents: Boron Tribromide Solvents: Dichloromethane; 1 H,Rt1.2 Reagents: Water Solvents: Water; 30 Min,Rt
    标题:Antioxidant Properties Of 3-Hydroxycoumarin Derivatives
    作者:Bailly,Fabrice; Maurin,Cedric; Teissier,Elisabeth; Vezin,Herve; Cotelle,Philippe
    参考文献:Bioorganic & Medicinal Chemistry 日期:2004 卷标:12(21) 页码:5611-5618]

    52900-70-6 = 939-19-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Heated
    标题:Novel Coupled Molecules From Active Structural Motifs Of Synthetic And Natural Origin As Immunosuppressants
    作者:Minhas,Richa; Bansal,Gulshan; Bansal,Yogita
    参考文献:Medicinal Chemistry (Sharjah 日期:2020 卷标:16(4) 页码:544-554]

    23891-02-3 = 939-19-5
    反应条件:1.1 Reagents: Cupric Chloride Catalysts: Palladium Chloride
    标题:Palladium(Ii) Catalyzed Oxidation Reactions Of Coumarin Derivatives
    作者:Mitra,Jayati; Mitra,Alok Kumar
    参考文献:Indian Journal Of Chemistry 日期:1992 卷标:(10) 页码:693-5]

    1635-31-0 = 939-19-5
    反应条件:1.1 Reagents: Hydrochloric Acid Catalysts: Potassium Cyanate
    标题:Some Reactions Of Aminocoumarins
    作者:Merchant,J. R.; Martyres,Gail; Venkatesh,M. S.
    参考文献:Indian Journal Of Chemistry 日期:1981 卷标:(6) 页码:493-5]

    = 939-19-5 [标题:Reaction Conditions
    标题:A Facile Synthesis Of 3-Hydroxycoumarin
    作者:Rajyalakshmi,K.; Srinivasan,V. R.
    参考文献:Indian Journal Of Chemistry 日期:1978 卷标:(2)]

    = 939-19-5 [标题:Reaction Conditions
    标题:3-Hydroxycoumarin
    参考文献:Ussr]

    = 939-19-5 [标题:Reaction Conditions
    标题:Pyran,Its Analogs,And Related Compounds. Xxv. Reaction Of 3-Bromocoumarin With Amines
    作者:Zagorevskii,V. A.; Savel'Ev,V. L.; Dudykina,N. V.; Portnova,S. L.
    参考文献:Zhurnal Organicheskoi Khimii 日期:1967 卷标:3(3) 页码:568-74
📜N-亚水杨基-3-氨基香豆素置于盐酸体系中,化学反应 2.0H,以67%的收率获得产物3-羟基香豆素
参考文献:取代香豆素的合成与研究.一种简便的d,L-邻酪氨酸制剂
标题:取代香豆素的合成与研究.一种简便的d,L-邻酪氨酸制剂
摘要:描述了在温和条件下制备氨基香豆素和氨基羟基香豆素的一般程序.通过在碳上含10%钯的情况下用硼氢化钠还原相应的硝基衍生物来制备氨基和乙酰氨基氨基香豆素.(a)在乙醇中的浓盐酸,或(b)1 N的乙酰胺基氨基香豆素的酸水解盐酸在回流下分别得到二氨基香豆素和氨基羟基香豆素.甘氨酸乙酯与水杨醛的缩合得到3-水杨基亚氨基香豆素(xiii),3-氨基香豆素的席夫碱(xii).在上述条件(a)和(b)下酸水解xiii,分别得到xii和3-羟基香豆素(xvi).在二恶烷或二甲基甲酰胺中用10%的钯在木炭上氢化化合物xiii得到3-水杨基氨基香豆素(xvii),而xii,Xiii或xvii在乙酸中用微量水和钯黑氢化则得到氨基酸邻酪氨酸.
DOI:10.1002/jhet.5570230118

海关参考信息

专利信息


专利号:US-2023235372-A1
优先权日:2020-06-12
标题:Ab-initio, template-independent synthesis of nucleic acids using thermostable enzymes
发明人：RANDRIANJATOVO-GBALOU IRINA; SAID AHMED; RAHIER RENAUD
权利人:SYNHELIX
摘要:The invention relates to the field of nucleic acid synthesis or sequencing, more specifically to methods for ab-initio synthesis of nucleic acids, comprising contacting a nucleotide with a free 3′-hydroxyl group, with at least one nucleoside triphosphate, or a combination of nucleoside triphosphates, in the presence of an archaeal DNA primase or a functionally active fragment and/or variant thereof, thereby covalently binding said nucleoside triphosphate to the free 3′-hydroxyl group of the nucleotide. It also relates to isolated functionally active fragments of archaeal DNA primases which are capable of both ab-initio single-stranded nucleic acid synthesis activity and template-independent terminal nucleotidyl transferase activity.

专利号:US-2023235373-A1
优先权日:2020-06-12
标 题:Controlled template-independent synthesis of nucleic acids using thermostable enzymes
发明人：RANDRIANJATOVO-GBALOU IRINA; SAID AHMED; RAHIER RENAUD
权利人:SYNHELIX
摘要:The invention relates to methods for template-independent synthesis of nucleic acids, comprising iteratively contacting an initiator sequence comprising a 3′-end nucleotide with a free 3′-hydroxyl group, with at least one nucleoside triphosphate, or a combination of nucleoside triphosphates, in the presence of an archaeal DNA primase or a functionally active fragment and/or variant thereof, thereby covalently binding said nucleoside triphosphate to the free 3-hydroxyl group of the 3-end nucleotide. It also relates to isolated functionally active fragments of archaeal DNA primases which are capable of template-independent terminal nucleotidyl transferase activity but are devoid of a template-independent primase activity.

专利号:US-7816544-B2
优先权日:2004-03-23
标 题:Synthesis of rocaglamide natural products via photochemical generation of oxidopyrylium species
发明人：JONES II GUILFORD; GERARD BAUDOUIN; PORCO JR JOHN A
权利人:UNIV BOSTON
摘要:The present invention provides new strategies for the synthesis of compounds of the rocaglamide family and related natural products. In particular, the new biomimetic synthetic approach involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile. This approach can be used for the formation of adducts containing an aglain core structure. Methods for the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.

专利号:US-10919904-B2
优先权日:2016-08-17
标 题 :Northern-southern route to synthesis of bacteriochlorins
发明人：LIU YIZHOU; LINDSEY JONATHAN S; ALLU SRINIVASA RAO; FUJITA HIKARU
权利人:UNIV NORTH CAROLINA STATE
摘要:Described herein are chlorins, bacteriochlorins, methods and intermediates for the synthesis of bacteriochlorins, and methods of using such bacteriochlorins for, among other things, diagnostic and therapeutic purposes such as luminescent compounds in flow cytometry, and as active agents in photodynamic therapy (PDT).

专利号:US-2010137421-A1
优先权日:2006-11-08
标题 :Small molecule therapeutics, synthesis of analogues and derivatives and methods of use
发明人：THEODORAKIS EMMANUEL; BATOVA AYSE
权利人:THEODORAKIS EMMANUEL; BATOVA AYSE
摘要:Provided herein are compounds that are inducers of apoptosis activators of caspases and pharmaceutically acceptable derivatives thereof. Also provided are methods of synthesis of the compounds and methods for treatment of diseases in which there is uncontrolled cell growth and spread of abnormal cells, such as cancers, by administering the compounds.

专利号:WO-03050105-A2
优先权日:2001-12-10
标题 :Catalytic asymmetric synthesis of optically active compounds
发明人：HALLAND NIS; JOERGENSEN KARL ANKER; HANSEN TORE
权利人:CHEMINOVA AS; HALLAND NIS; JOERGENSEN KARL ANKER; HANSEN TORE
摘要:A one step catalytic asymmetric process for the synthesis of an optically active compound of formula la or lb wherein R is selected from C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, C1-7 haloalkoxy, halogen and hydroxy; R3 is H or C1-4 alkyl; R4 is selected from H, C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, COOH, CO-C1-7 alkoxy and an optionally substituted aryl or heterocycle; AR represents C1-7 alkyl, optionally substituted aryl, an optionally substituted heterocycle or AR and R4 may be bridged together forming part of a ring system; X is O or S; m is a number between 0-4; comprising the step of reacting a compound of the formula 2 with a compound of formula 3 in the presence of a catalytic amount of a chiral nitrogen containing organic compound.

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合成参考文献


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参考文献:10.1124/dmd.30.5.483
摘要:Born SL, Caudill D, Fliter KL, Purdon MP. Identification of the cytochromes P450 that catalyze coumarin 3,4-epoxidation and 3-hydroxylation. Drug Metab Dispos. 2002 May;30(5):483–7. doi: 10.1124/dmd.30.5.483.
参考文献:10.1023/b:plan.0000028775.58537.fe
摘要:Gachon C, Baltz R, Saindrenan P. Over-expression of a scopoletin glucosyltransferase in Nicotiana tabacum leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance. Plant Mol Biol. 2004 Jan;54(1):137–46. doi: 10.1023/b:plan.0000028775.58537.fe.
参考文献:10.1039/c5pp00318k
摘要:Khanna R, Dalal A, Kumar R, Kamboj RC. Phototransformation of 3-alkoxychromenones: regioselective photocyclisation and dealkoxylation. Photochemical & Photobiological Sciences. 2015 Dec 01;14(12):2195–202. doi: 10.1039/c5pp00318k.
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