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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
    —— (4S)-3-(2,3-dihydro-1-benzofuran-5-yl)-6-imino-1,4-dimethyl-4-(4-pyrimidin-5-ylthiophen-2-yl)piperidin-2-one —— C23H22N4O2S
    (4S)-3-(2,3-dihydro-1-benzofuran-5-yl)-6-imino-1,4-dimethyl-4-(4-pyrimidin-5-ylthiophen-2-yl)piperidin-2-one
    —— 9-carbazol-9-yl-N-methyl-N-(2-methylphenyl)-5a,10b-diphenyl-[1]benzofuro[2,3-b][1]benzofuran-2-amine —— C46H34N2O2
    9-carbazol-9-yl-N-methyl-N-(2-methylphenyl)-5a,10b-diphenyl-[1]benzofuro[2,3-b][1]benzofuran-2-amine
    —— N-(3-morpholin-4-ylpropyl)-1,4-dioxido-6,7-dihydro-2H-furo[3,2-g][1,2,4]benzotriazin-3-imine —— C16H21N5O4-2
    N-(3-morpholin-4-ylpropyl)-1,4-dioxido-6,7-dihydro-2H-furo[3,2-g][1,2,4]benzotriazin-3-imine
    —— 2-(Azidomethyl)-7-(4-chloro-2-methylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran —— C16H13ClFN3O
    2-(Azidomethyl)-7-(4-chloro-2-methylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran
    —— (2,2-difluoro-3H-1-benzofuran-5-yl)methanol —— C9H8F2O2
    (2,2-difluoro-3H-1-benzofuran-5-yl)methanol
    —— N-[2-(5-carbamimidoyl-2,3-dihydro-1-benzofuran-3-yl)ethyl]-3-phenylpropanamide —— C20H23N3O2
    N-[2-(5-carbamimidoyl-2,3-dihydro-1-benzofuran-3-yl)ethyl]-3-phenylpropanamide
    —— [7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl] N-benzyl-N-methylcarbamate —— C23H20FNO3
    [7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl] N-benzyl-N-methylcarbamate
    —— (6-Methoxy-2,3-dihydro-1-benzofuran-3-yl) propanoate —— C12H14O4
    (6-Methoxy-2,3-dihydro-1-benzofuran-3-yl) propanoate
    —— 1-[3-(diethylamino)propyl]-5-(furan-2-yl)-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1,5-dihydro-2H-pyrrol-2-one —— C25H30N2O5
    1-[3-(diethylamino)propyl]-5-(furan-2-yl)-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1,5-dihydro-2H-pyrrol-2-one
    —— methyl (7E)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C27H19ClN2O5S
    methyl (7E)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
    —— (9aS)-8-acetyl-1-hydroxy-N-[(4-hydroxy-2,3,5,6-tetramethylphenyl)methyl]-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide —— C28H29NO8
    (9aS)-8-acetyl-1-hydroxy-N-[(4-hydroxy-2,3,5,6-tetramethylphenyl)methyl]-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide
    —— 5-[(1R,2R,3aS,8bS)-2-hydroxy-1-[(3S)-3-hydroxyoct-1-enyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]-N,N-dimethylpentanamide —— C26H39NO4
    5-[(1R,2R,3aS,8bS)-2-hydroxy-1-[(3S)-3-hydroxyoct-1-enyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]-N,N-dimethylpentanamide
    —— 4-(2-Chloro-5-fluoroanilino)-2-(2,3-dihydro-1-benzofuran-6-yl)-1,3-thiazole-5-carboxamide —— C18H13ClFN3O2S
    4-(2-Chloro-5-fluoroanilino)-2-(2,3-dihydro-1-benzofuran-6-yl)-1,3-thiazole-5-carboxamide
    —— 2-methylidene-3H-1-benzofuran-3-ide —— C9H7O-
    2-methylidene-3H-1-benzofuran-3-ide
    —— 4-[(1R,2R,3aS,8bS)-2-hydroxy-1-[(3S,4S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]-N,N-diethylbutanamide —— C28H39NO4
    4-[(1R,2R,3aS,8bS)-2-hydroxy-1-[(3S,4S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]-N,N-diethylbutanamide
    —— 1-(2,3-Dihydro-1-benzofuran-2-yl)-2-phenylbutan-1-one —— C18H18O2
    1-(2,3-Dihydro-1-benzofuran-2-yl)-2-phenylbutan-1-one
    —— 2,3-Dihydro-1-benzofuran;tetramethylsilane —— C12H20OSi
    2,3-Dihydro-1-benzofuran;tetramethylsilane
    —— (1-Carbamoyl-4-oxo-2-pyridin-4-yl-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl) 2,3-dihydro-1-benzofuran-2-carboxylate —— C22H20N4O5
    (1-Carbamoyl-4-oxo-2-pyridin-4-yl-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl) 2,3-dihydro-1-benzofuran-2-carboxylate
    —— 1-[[7-(2-Chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[[7-(2-methoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl]hydrazine —— C33H33ClN2O3
    1-[[7-(2-Chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[[7-(2-methoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl]hydrazine
    —— (5-chloro-2,2-dimethyl-3H-1-benzofuran-7-yl)methanetriol —— C11H13ClO4
    (5-chloro-2,2-dimethyl-3H-1-benzofuran-7-yl)methanetriol
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-imidazol-1-ylpropyl)-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione —— C25H25N3O5
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-imidazol-1-ylpropyl)-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione
    —— 5-[[4-[[3,4-bis(fluoromethylidene)-2-oxocyclohexylidene]amino]-5-fluoropyrimidin-2-yl]amino]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H18F3N5O3
    5-[[4-[[3,4-bis(fluoromethylidene)-2-oxocyclohexylidene]amino]-5-fluoropyrimidin-2-yl]amino]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,3,5,6-tetramethyl-4-pent-2-ynoxyphenyl)methyl]dibenzofuran-4-carboxamide —— C33H35NO8
    (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,3,5,6-tetramethyl-4-pent-2-ynoxyphenyl)methyl]dibenzofuran-4-carboxamide
    —— 5-[[4-(3-Tert-butylanilino)-5-fluoropyrimidin-2-yl]amino]-2,3-dihydro-1-benzofuran-2-carbaldehyde —— C23H23FN4O2
    5-[[4-(3-Tert-butylanilino)-5-fluoropyrimidin-2-yl]amino]-2,3-dihydro-1-benzofuran-2-carbaldehyde
    —— (1Z)-2-methyl-1-[3-(morpholin-4-yl)-5-nitro-1-benzofuran-2(3H)-ylidene]propan-2-ol —— C16H20N2O5
    (1Z)-2-methyl-1-[3-(morpholin-4-yl)-5-nitro-1-benzofuran-2(3H)-ylidene]propan-2-ol
    —— 5-methyl-2-methylidene-3H-1-benzofuran-3-ide —— C10H9O-
    5-methyl-2-methylidene-3H-1-benzofuran-3-ide
    —— 1-[7-(3-Chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C16H16ClNO
    1-[7-(3-Chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— 5,7-ditert-butyl-3-(4-hydroxy-3,5-dimethylphenyl)-3H-1-benzofuran-2-one;5,7-ditert-butyl-3-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3H-1-benzofuran-2-one;5,7-ditert-butyl-3-(3,4,5-trimethylphenyl)-3H-1-benzofuran-2-one —— C75H96O9
    5,7-ditert-butyl-3-(4-hydroxy-3,5-dimethylphenyl)-3H-1-benzofuran-2-one;5,7-ditert-butyl-3-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3H-1-benzofuran-2-one;5,7-ditert-butyl-3-(3,4,5-trimethylphenyl)-3H-1-benzofuran-2-one
    —— [(3S)-6-[[(3S)-7-[(4-methylpyridin-2-yl)amino]-2,3-dihydro-1-benzofuran-3-yl]amino]-2,3-dihydro-1-benzofuran-3-yl] propanoate —— C25H25N3O4
    [(3S)-6-[[(3S)-7-[(4-methylpyridin-2-yl)amino]-2,3-dihydro-1-benzofuran-3-yl]amino]-2,3-dihydro-1-benzofuran-3-yl] propanoate
    —— 5-[[4-(4-butan-2-yloxyphenyl)cycloheptyl]methyl]-7-ethoxy-6-ethyl-2-(ethylsulfanylmethyl)-2,4-dimethyl-3H-1-benzofuran —— C35H52O3S
    5-[[4-(4-butan-2-yloxyphenyl)cycloheptyl]methyl]-7-ethoxy-6-ethyl-2-(ethylsulfanylmethyl)-2,4-dimethyl-3H-1-benzofuran
    —— [5-chloro-7-(2,3-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl N-benzylcarbamate —— C23H18ClF2NO3
    [5-chloro-7-(2,3-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl N-benzylcarbamate
    —— N,N-dimethyl-2-[(1-oxido-2,4,6,7-tetrahydro-1H-furo[3,2-g][1,2,4]benzotriazin-1-ium-3-ylidene)amino]ethanamine —— C13H19N5O2
    N,N-dimethyl-2-[(1-oxido-2,4,6,7-tetrahydro-1H-furo[3,2-g][1,2,4]benzotriazin-1-ium-3-ylidene)amino]ethanamine
    —— 1-[7-(2,6-Dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C16H15Cl2NO
    1-[7-(2,6-Dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— [4,6,7-trimethyl-3-(4-propan-2-ylphenyl)-2,3-dihydro-1-benzofuran-5-yl] N-tert-butylcarbamate —— C25H33NO3
    [4,6,7-trimethyl-3-(4-propan-2-ylphenyl)-2,3-dihydro-1-benzofuran-5-yl] N-tert-butylcarbamate
    —— (9aS)-8-acetyl-N-[(3-fluoro-2-methylphenyl)methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide —— C25H22FNO7
    (9aS)-8-acetyl-N-[(3-fluoro-2-methylphenyl)methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide
    —— 4-Oxatricyclo[7.6.0.03,7]pentadeca-1(9),2,7,10,12,14-hexaene —— C14H12O
    4-Oxatricyclo[7.6.0.03,7]pentadeca-1(9),2,7,10,12,14-hexaene
    —— N'-[4-[[1-(4-fluorophenyl)-3,6,7,8-tetrahydro-2H-pyrido[1,2-b]pyridazin-5-ylidene]methyl]-2,3-dihydro-1-benzofuran-7-yl]-N'-(2-iminopropyl)methanediamine —— C27H32FN5O
    N'-[4-[[1-(4-fluorophenyl)-3,6,7,8-tetrahydro-2H-pyrido[1,2-b]pyridazin-5-ylidene]methyl]-2,3-dihydro-1-benzofuran-7-yl]-N'-(2-iminopropyl)methanediamine
    —— (7-bromo-2,2,4,6-tetramethyl-3H-1-benzofuran-5-yl) N-tert-butylcarbamate —— C17H24BrNO3
    (7-bromo-2,2,4,6-tetramethyl-3H-1-benzofuran-5-yl) N-tert-butylcarbamate
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione —— C26H29N3O5
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— 2-N-(3-chloro-4-fluorophenyl)-5-(2,3-dihydro-1-benzofuran-2-yl)-4-N-[3-(dimethylamino)propyl]pyrimidine-2,4-diamine —— C23H25ClFN5O
    2-N-(3-chloro-4-fluorophenyl)-5-(2,3-dihydro-1-benzofuran-2-yl)-4-N-[3-(dimethylamino)propyl]pyrimidine-2,4-diamine
    —— (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]dibenzofuran-4-carboxamide —— C24H18F3NO7
    (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,4,6-trifluorophenyl)methyl]dibenzofuran-4-carboxamide
    —— 1-[3-(diethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one —— C25H30N2O4S
    1-[3-(diethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one
    —— (4E)-1-[3-(diethylamino)propyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione —— C25H30N2O4S
    (4E)-1-[3-(diethylamino)propyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 4-Tert-butyl-7-ethyl-2,3-dihydro-1-benzofuran —— C14H20O
    4-Tert-butyl-7-ethyl-2,3-dihydro-1-benzofuran
    —— Ethane;5-methoxy-2,3-dihydro-1-benzofuran-6-carbaldehyde —— C12H16O3
    Ethane;5-methoxy-2,3-dihydro-1-benzofuran-6-carbaldehyde
    —— 1-(2-furylmethyl)-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(2-thienyl)-1,5-dihydro-2H-pyrrol-2-one —— C23H19NO5S
    1-(2-furylmethyl)-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(2-thienyl)-1,5-dihydro-2H-pyrrol-2-one
    —— 5-(furan-2-yl)-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1-(tetrahydrofuran-2-ylmethyl)-1,5-dihydro-2H-pyrrol-2-one —— C23H23NO6
    5-(furan-2-yl)-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1-(tetrahydrofuran-2-ylmethyl)-1,5-dihydro-2H-pyrrol-2-one
    —— 1-[3-(dimethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(4-pyridinyl)-1,5-dihydro-2H-pyrrol-2-one —— C24H27N3O4
    1-[3-(dimethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(4-pyridinyl)-1,5-dihydro-2H-pyrrol-2-one
    —— carbamoyl 7-[5-formyl-2-(trifluoromethoxy)phenyl]-3,3-dimethyl-2H-1-benzofuran-5-carboxylate —— C20H16F3NO6
    carbamoyl 7-[5-formyl-2-(trifluoromethoxy)phenyl]-3,3-dimethyl-2H-1-benzofuran-5-carboxylate
    —— [4-[di(propan-2-yl)carbamoyloxy]-2,3-dihydro-1-benzofuran-6-yl] N,N-di(propan-2-yl)carbamate —— C22H34N2O5
    [4-[di(propan-2-yl)carbamoyloxy]-2,3-dihydro-1-benzofuran-6-yl] N,N-di(propan-2-yl)carbamate