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    首页 分子通 按分子结构分类 有机化合物 有机杂环化合物 香豆素

    香豆素

    香豆素 基本信息

    香豆素（Coumarin）是一类具有独特芳香气味的化合物，化学式为C9H6O2。它们属于苯骈α-呋喃酮类化合物，在自然界中广泛存在。

    结构特征

    香豆素的基本结构由苯环和呋喃酮构成，其中苯环与四个碳原子相连的呋喃酮单元形成独特的“香豆素环”。

    自然来源

    香豆素存在于多种植物、真菌及动物体内。在植物界中，它主要作为天然防御机制的一部分，用作对昆虫的化学信号。著名的例子包括：天竺葵科（如紫花苜蓿）、唇形科（如薄荷）和芸香科（如柑橘属果实）。此外，在真菌、苔藓及藻类中也有发现。

    化学性质 稳定性

    由于其独特的结构，香豆素表现出良好的化学稳定性。它们不易被氧化或还原，但可以与其他化合物发生多种类型的反应，包括缩合、取代等。

    生物活性

    许多香豆素衍生物具有生物活性，能够引起抗菌、抗炎、抗氧化等多种作用。这些特性使它们成为医药、食品添加剂等多个领域的重要研究对象。

    应用领域 医药行业

    在制药业中，某些结构类似物被开发为药物先导化合物。例如，香豆素类抗生素是最早的广谱抗生素之一；一些香豆素衍生物还表现出抗癌潜力。

    食品工业

    由于其独特的香气和味道，在食品加工中也得到了广泛应用，常作为香精成分使用。

    其他应用

    此外，它们还在染料生产、农药开发等多个领域展现出潜在价值。

    生产方法

    香豆素可通过多种合成路径获得。传统的化学合成涉及从苯甲醛出发的反应；而近年来，通过生物转化技术，利用微生物发酵过程制备天然香豆素也成为一种可持续的方法。

    总之，香豆素因其独特的结构和广泛的生物学应用，在多个领域中发挥着重要作用，并且仍然是有机化学研究中的一个重要课题。

    相关化合物

    中文名称 英文名称 CAS号 化学式 结构式图片
    —— (2R)-2-(4-phenylbutyl)-2,3-dihydro-1-benzofuran —— C18H20O
    (2R)-2-(4-phenylbutyl)-2,3-dihydro-1-benzofuran
    —— (9aS)-8-acetyl-N-[(2,5-difluorophenyl)methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide —— C24H19F2NO7
    (9aS)-8-acetyl-N-[(2,5-difluorophenyl)methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide
    —— 2-[2-[3-fluoro-4-[(5-fluoro-2,2-dimethyl-3H-1-benzofuran-7-yl)methoxy]phenyl]cyclopropyl]acetic acid —— C22H22F2O4
    2-[2-[3-fluoro-4-[(5-fluoro-2,2-dimethyl-3H-1-benzofuran-7-yl)methoxy]phenyl]cyclopropyl]acetic acid
    —— 2-ethyl-4-[4-[(5-fluoro-2,2-dimethyl-3H-1-benzofuran-7-yl)methoxy]phenyl]-2-methyl-3-sulfanylbutanoic acid —— C24H29FO4S
    2-ethyl-4-[4-[(5-fluoro-2,2-dimethyl-3H-1-benzofuran-7-yl)methoxy]phenyl]-2-methyl-3-sulfanylbutanoic acid
    —— (1R,2R,3aS,8bS)-1-[(3S,4S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-5-[4-(propan-2-ylamino)butyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-ol —— C27H39NO3
    (1R,2R,3aS,8bS)-1-[(3S,4S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-5-[4-(propan-2-ylamino)butyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-ol
    —— 2-[(E)-(3-nitroso-3H-1-benzofuran-2-ylidene)amino]oxyethanol —— C10H10N2O4
    2-[(E)-(3-nitroso-3H-1-benzofuran-2-ylidene)amino]oxyethanol
    —— 4-(4-chloroanilino)-1-[3-[[2,2-dimethyl-5-[methyl(sulfino)amino]-3H-1-benzofuran-7-yl]oxy]propyl]piperidine —— C25H34ClN3O4S
    4-(4-chloroanilino)-1-[3-[[2,2-dimethyl-5-[methyl(sulfino)amino]-3H-1-benzofuran-7-yl]oxy]propyl]piperidine
    —— 4-(4-chloroanilino)-1-[3-[[2,2-dimethyl-5-[methyl(sulfinato)amino]-3H-1-benzofuran-7-yl]oxy]propyl]piperidine —— C25H33ClN3O4S-
    4-(4-chloroanilino)-1-[3-[[2,2-dimethyl-5-[methyl(sulfinato)amino]-3H-1-benzofuran-7-yl]oxy]propyl]piperidine
    —— 6-piperidin-1-yl-1'-(3-propylcyclobutyl)spiro[3H-1-benzofuran-2,4'-azepane] —— C25H38N2O
    6-piperidin-1-yl-1'-(3-propylcyclobutyl)spiro[3H-1-benzofuran-2,4'-azepane]
    —— N-[4-(2,3-dihydro-1-benzofuran-2-yl)piperazin-1-yl]pyrimidin-2-amine —— C16H19N5O
    N-[4-(2,3-dihydro-1-benzofuran-2-yl)piperazin-1-yl]pyrimidin-2-amine
    —— (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid 4-chloro-benzylamide —— C24H20ClNO7
    (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid 4-chloro-benzylamide
    —— (3S)-9b-ethyl-6-methoxy-9-(methylaminomethyl)-4,4a-dihydro-3H-dibenzofuran-3-ol —— C17H23NO3
    (3S)-9b-ethyl-6-methoxy-9-(methylaminomethyl)-4,4a-dihydro-3H-dibenzofuran-3-ol
    —— 10-Ethoxy-2,8-dioxapentacyclo[11.3.2.03,15.07,15.09,14]octadeca-9,11,13-trien-5-one —— C18H20O4
    10-Ethoxy-2,8-dioxapentacyclo[11.3.2.03,15.07,15.09,14]octadeca-9,11,13-trien-5-one
    —— 1-[7-(5-Chloro-2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C17H18ClNO2
    1-[7-(5-Chloro-2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— (1-carbamoyl-4-oxo-2-pyridin-4-yl-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl) 2,2-dimethyl-3H-1-benzofuran-7-carboxylate —— C24H24N4O5
    (1-carbamoyl-4-oxo-2-pyridin-4-yl-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl) 2,2-dimethyl-3H-1-benzofuran-7-carboxylate
    —— 4-(2-Amino-1-hydroxyethyl)-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-7-ol —— C17H19NO5
    4-(2-Amino-1-hydroxyethyl)-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-7-ol
    —— N-(10-methyl-4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrimido[1,2-a]azepin-10-yl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C24H24N4O3
    N-(10-methyl-4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrimido[1,2-a]azepin-10-yl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— 1-(2,3-dihydro-1-benzofuran-7-ylsulfonyl)-N-methyl-2-[(Z)-prop-1-enyl]-4-pyrrolidin-3-ylpyrrol-3-amine —— C20H25N3O3S
    1-(2,3-dihydro-1-benzofuran-7-ylsulfonyl)-N-methyl-2-[(Z)-prop-1-enyl]-4-pyrrolidin-3-ylpyrrol-3-amine
    —— [7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl N-benzylcarbamate —— C24H23NO4
    [7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl N-benzylcarbamate
    —— 2-[(1-Hydroxy-2,2,5,5-tetramethylpyrrol-3-yl)methylamino]-1-(2,3,5,8-tetrahydrodithiino[4,5-f][1]benzofuran-2-yl)ethanol —— C21H30N2O3S2
    2-[(1-Hydroxy-2,2,5,5-tetramethylpyrrol-3-yl)methylamino]-1-(2,3,5,8-tetrahydrodithiino[4,5-f][1]benzofuran-2-yl)ethanol
    —— (4aS,9aR)-4a-ethyl-2,3,4,9a-tetrahydro-1H-[1]benzofuro[2,3-c]pyridin-8-ol —— C13H17NO2
    (4aS,9aR)-4a-ethyl-2,3,4,9a-tetrahydro-1H-[1]benzofuro[2,3-c]pyridin-8-ol
    —— 5-Ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-carbaldehyde —— C12H14O3
    5-Ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-carbaldehyde
    —— N-[5-(1-methyl-3-pyridin-4-ylpyrazol-4-yl)-1-benzofuran-3-ylidene]hydroxylamine —— C17H14N4O2
    N-[5-(1-methyl-3-pyridin-4-ylpyrazol-4-yl)-1-benzofuran-3-ylidene]hydroxylamine
    —— N,N-diethyl-2-[(1-oxido-2,4,7,8-tetrahydrofuro[2,3-g][1,2,4]benzotriazin-3-ylidene)amino]ethanamine —— C15H22N5O2-
    N,N-diethyl-2-[(1-oxido-2,4,7,8-tetrahydrofuro[2,3-g][1,2,4]benzotriazin-3-ylidene)amino]ethanamine
    —— 2-[(4S)-5-hydroxy-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]pentyl]guanidine —— C19H32N4O4S
    2-[(4S)-5-hydroxy-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]pentyl]guanidine
    —— 3-(5-bromothiophen-3-yl)-N-(2-methoxyethyl)-N-methyl-8bH-[1]benzofuro[3,2-c]pyrazol-6-amine —— C17H16BrN3O2S
    3-(5-bromothiophen-3-yl)-N-(2-methoxyethyl)-N-methyl-8bH-[1]benzofuro[3,2-c]pyrazol-6-amine
    —— 3,3,5,7-tetramethyl-2H-1-benzofuran —— C12H16O
    3,3,5,7-tetramethyl-2H-1-benzofuran
    —— (2S)-N-(4-oxo-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-10-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H21N5O3
    (2S)-N-(4-oxo-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-10-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-[3-(5,7-dimethyl-2-oxo-3H-1-benzofuran-3-yl)-4-(2-methoxyethoxy)phenoxy]ethyl N-(6-acetamidohexyl)carbamate;2-[3-(5,7-dimethyl-2-oxo-3H-1-benzofuran-3-yl)-4-(2-methoxyethoxy)phenoxy]ethyl 6-oxoheptanoate —— C58H74N2O16
    2-[3-(5,7-dimethyl-2-oxo-3H-1-benzofuran-3-yl)-4-(2-methoxyethoxy)phenoxy]ethyl N-(6-acetamidohexyl)carbamate;2-[3-(5,7-dimethyl-2-oxo-3H-1-benzofuran-3-yl)-4-(2-methoxyethoxy)phenoxy]ethyl 6-oxoheptanoate
    —— [7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl] N-benzyl-N-methylcarbamate —— C24H23NO4
    [7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl] N-benzyl-N-methylcarbamate
    —— 1-[7-(2,5-Dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C16H15Cl2NO
    1-[7-(2,5-Dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— 2-[4-Methyl-3-(4-propan-2-ylphenyl)-2,3-dihydrobenzo[g][1]benzofuran-5-yl]acetic acid —— C24H24O3
    2-[4-Methyl-3-(4-propan-2-ylphenyl)-2,3-dihydrobenzo[g][1]benzofuran-5-yl]acetic acid
    —— N-(3-morpholin-4-ylpropyl)-1-oxido-2,4,7,8-tetrahydro-1H-furo[2,3-g][1,2,4]benzotriazin-1-ium-3-imine —— C16H23N5O3
    N-(3-morpholin-4-ylpropyl)-1-oxido-2,4,7,8-tetrahydro-1H-furo[2,3-g][1,2,4]benzotriazin-1-ium-3-imine
    —— (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,4,6-triethylphenyl)methyl]dibenzofuran-4-carboxamide —— C30H33NO7
    (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,4,6-triethylphenyl)methyl]dibenzofuran-4-carboxamide
    —— 1,4-Dioxido-7,8-dihydrofuro[2,3-g][1,2,4]benzotriazin-3-amine —— C9H8N4O3-2
    1,4-Dioxido-7,8-dihydrofuro[2,3-g][1,2,4]benzotriazin-3-amine
    —— 1,4-Dioxido-1,4,7,8-tetrahydrofuro[2,3-g][1,2,4]benzotriazine-1,4-diium-3-amine —— C9H10N4O3
    1,4-Dioxido-1,4,7,8-tetrahydrofuro[2,3-g][1,2,4]benzotriazine-1,4-diium-3-amine
    —— N-cyclohexyl-2-methyl-2,3-dihydro-1-benzofuran-5-carboxamide —— C16H21NO2
    N-cyclohexyl-2-methyl-2,3-dihydro-1-benzofuran-5-carboxamide
    —— ethyl 8bH-[1]benzofuro[3,2-b]pyrrole-2-carboxylate —— C13H11NO3
    ethyl 8bH-[1]benzofuro[3,2-b]pyrrole-2-carboxylate
    —— 9-Hydroxy-11-oxatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-one —— C16H16O3
    9-Hydroxy-11-oxatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-one
    —— (7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl N-benzyl-N-methylcarbamate —— C23H22N2O3
    (7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl N-benzyl-N-methylcarbamate
    —— (2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methyl carbamimidothioate —— C11H14N2OS
    (2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methyl carbamimidothioate
    —— 1-oxido-6,7-dihydro-2H-furo[3,2-g][1,2,4]benzotriazin-3-amine —— C9H9N4O2-
    1-oxido-6,7-dihydro-2H-furo[3,2-g][1,2,4]benzotriazin-3-amine
    —— 1-Oxido-1,4,6,7-tetrahydrofuro[3,2-g][1,2,4]benzotriazin-1-ium-3-amine —— C9H10N4O2
    1-Oxido-1,4,6,7-tetrahydrofuro[3,2-g][1,2,4]benzotriazin-1-ium-3-amine
    —— 1-phenyl-N-[(2,4,6,7-tetramethyl-3H-1-benzofuran-2-yl)methyl]ethanamine —— C21H27NO
    1-phenyl-N-[(2,4,6,7-tetramethyl-3H-1-benzofuran-2-yl)methyl]ethanamine
    —— (9aS)-8-acetyl-N-[[4-(but-2-ynoxymethyl)-2,3,6-trimethylphenyl]methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide —— C32H33NO8
    (9aS)-8-acetyl-N-[[4-(but-2-ynoxymethyl)-2,3,6-trimethylphenyl]methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide
    —— 2-(2,3-Dihydro-1-benzofuran-3-yl)pyrimidine —— C12H10N2O
    2-(2,3-Dihydro-1-benzofuran-3-yl)pyrimidine
    —— [(3S)-6-(trifluoromethylsulfonyloxy)-2,3-dihydro-1-benzofuran-3-yl] propanoate —— C12H11F3O6S
    [(3S)-6-(trifluoromethylsulfonyloxy)-2,3-dihydro-1-benzofuran-3-yl] propanoate
    —— 16-(Cyclobutylmethyl)-5-methoxy-7-oxa-16-azapentacyclo[10.6.1.01,6.02,15.08,19]nonadeca-2,4,8,10,12(19)-pentaen-9-ol —— C23H27NO3
    16-(Cyclobutylmethyl)-5-methoxy-7-oxa-16-azapentacyclo[10.6.1.01,6.02,15.08,19]nonadeca-2,4,8,10,12(19)-pentaen-9-ol
    —— 2-(2-Chloro-4-fluoro-5-methylphenyl)imino-5-(2,3-dihydro-1-benzofuran-2-ylmethylidene)-1,3-thiazolidin-4-one —— C19H14ClFN2O2S
    2-(2-Chloro-4-fluoro-5-methylphenyl)imino-5-(2,3-dihydro-1-benzofuran-2-ylmethylidene)-1,3-thiazolidin-4-one
    —— 3-(5-Ethyl-2,3-dihydro-1-benzofuran-4-yl)but-2-enenitrile —— C14H15NO
    3-(5-Ethyl-2,3-dihydro-1-benzofuran-4-yl)but-2-enenitrile