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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
    —— 1-(1,5-Dimethoxy-13-methyl-3-oxa-13-azapentacyclo[13.2.2.18,14.02,10.04,9]icosa-4,6,8-trien-17-yl)ethanone —— C23H31NO4
    1-(1,5-Dimethoxy-13-methyl-3-oxa-13-azapentacyclo[13.2.2.18,14.02,10.04,9]icosa-4,6,8-trien-17-yl)ethanone
    —— 2-[(1,4-dioxido-7,8-dihydro-2H-furo[2,3-g][1,2,4]benzotriazin-3-ylidene)amino]-N,N-diethylethanamine —— C15H21N5O3-2
    2-[(1,4-dioxido-7,8-dihydro-2H-furo[2,3-g][1,2,4]benzotriazin-3-ylidene)amino]-N,N-diethylethanamine
    —— 6-Bromo-3-(2,3-dihydro-1-benzofuran-5-carbonyl)-7-methyl-1-benzofuran-4,5-dione —— C18H11BrO5
    6-Bromo-3-(2,3-dihydro-1-benzofuran-5-carbonyl)-7-methyl-1-benzofuran-4,5-dione
    —— N-oxo-2,3-dihydro-1-benzofuran-5-carboxamide —— C9H7NO3
    N-oxo-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 1-[7-(2,3-Difluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C17H14F5NO
    1-[7-(2,3-Difluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— 3-spiro[3H-1-benzofuran-2,2'-adamantane]-5-yl-1H-pyrrole —— C21H23NO
    3-spiro[3H-1-benzofuran-2,2'-adamantane]-5-yl-1H-pyrrole
    —— 3-hydroxy-1-(2-methoxyethyl)-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-5-(5-methylfuran-2-yl)-2,5-dihydro-1H-pyrrol-2-one —— C22H23NO6
    3-hydroxy-1-(2-methoxyethyl)-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-5-(5-methylfuran-2-yl)-2,5-dihydro-1H-pyrrol-2-one
    —— 2-[(1,4-dioxido-7,8-dihydro-2H-furo[2,3-g][1,2,4]benzotriazin-3-ylidene)amino]-N,N-dimethylethanamine —— C13H17N5O3-2
    2-[(1,4-dioxido-7,8-dihydro-2H-furo[2,3-g][1,2,4]benzotriazin-3-ylidene)amino]-N,N-dimethylethanamine
    —— 7-Fluoro-4-phenyl-2,3-dihydro-1-benzofuran —— C14H11FO
    7-Fluoro-4-phenyl-2,3-dihydro-1-benzofuran
    —— 2,3,4,4a,5,6,6a,11b-Octahydro-[1]benzofuro[2,3-h]quinazolin-2-amine —— C14H17N3O
    2,3,4,4a,5,6,6a,11b-Octahydro-[1]benzofuro[2,3-h]quinazolin-2-amine
    —— (1-carbamoyl-4-oxo-2-pyridin-4-yl-6,7,8,9,10,10a-hexahydropyrimido[1,2-a]azepin-10-yl) 2,2-dimethyl-3H-1-benzofuran-7-carboxylate —— C26H28N4O5
    (1-carbamoyl-4-oxo-2-pyridin-4-yl-6,7,8,9,10,10a-hexahydropyrimido[1,2-a]azepin-10-yl) 2,2-dimethyl-3H-1-benzofuran-7-carboxylate
    —— 2-[[2,2,4,6,7-pentamethyl-3-(4-propan-2-ylphenyl)-3H-1-benzofuran-5-yl]oxy]-2-phenylpropanoic acid —— C31H36O4
    2-[[2,2,4,6,7-pentamethyl-3-(4-propan-2-ylphenyl)-3H-1-benzofuran-5-yl]oxy]-2-phenylpropanoic acid
    —— N,N-diethyl-2-[(1-oxido-2,4,7,8-tetrahydro-1H-furo[2,3-g][1,2,4]benzotriazin-1-ium-3-ylidene)amino]ethanamine —— C15H23N5O2
    N,N-diethyl-2-[(1-oxido-2,4,7,8-tetrahydro-1H-furo[2,3-g][1,2,4]benzotriazin-1-ium-3-ylidene)amino]ethanamine
    —— N-[1-(6-oxo-4-pyrimidin-4-yl-1H-pyrimidin-2-yl)ethyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C19H17N5O3
    N-[1-(6-oxo-4-pyrimidin-4-yl-1H-pyrimidin-2-yl)ethyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— 2,3-Dihydro-1-benzofuran-7-yl trifluoromethanesulfonate —— C9H7F3O4S
    2,3-Dihydro-1-benzofuran-7-yl trifluoromethanesulfonate
    —— 3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1-(2-phenylethyl)-5-(2-thienyl)-1,5-dihydro-2H-pyrrol-2-one —— C26H23NO4S
    3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1-(2-phenylethyl)-5-(2-thienyl)-1,5-dihydro-2H-pyrrol-2-one
    —— N-(3-morpholin-4-ylpropyl)-1-oxido-2,4,7,8-tetrahydrofuro[2,3-g][1,2,4]benzotriazin-3-imine —— C16H22N5O3-
    N-(3-morpholin-4-ylpropyl)-1-oxido-2,4,7,8-tetrahydrofuro[2,3-g][1,2,4]benzotriazin-3-imine
    —— [(Z)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(4-methylphenyl)carbamate —— C18H18N2O3
    [(Z)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(4-methylphenyl)carbamate
    —— (9aS)-8-acetyl-1-hydroxy-N-[(4-hydroxy-2,3,6-trimethylphenyl)methyl]-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide —— C27H27NO8
    (9aS)-8-acetyl-1-hydroxy-N-[(4-hydroxy-2,3,6-trimethylphenyl)methyl]-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide
    —— (E)-{1-[3-(dimethylammonio)propyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene}(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate —— C24H28N2O5
    (E)-{1-[3-(dimethylammonio)propyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene}(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate
    —— 2,4-Dichlorophenyl {2-[3-morpholino-5-nitro-1-benzofuran-2(3H)-yliden]ethyl} ether —— C20H18Cl2N2O5
    2,4-Dichlorophenyl {2-[3-morpholino-5-nitro-1-benzofuran-2(3H)-yliden]ethyl} ether
    —— (2-Bromo-2,3-dihydro-1-benzofuran-3-yl)methanol —— C9H9BrO2
    (2-Bromo-2,3-dihydro-1-benzofuran-3-yl)methanol
    —— ethane;3-(2-methoxy-5-methylphenyl)-5-methyl-3H-1-benzofuran-2-one —— C21H28O3
    ethane;3-(2-methoxy-5-methylphenyl)-5-methyl-3H-1-benzofuran-2-one
    —— 2-aminopyridine-3-carbaldehyde;1-[(1S)-1-(2,3-dihydro-1-benzofuran-6-yl)propyl]-3-(4-oxopentyl)pyrrolidin-2-one —— C26H33N3O4
    2-aminopyridine-3-carbaldehyde;1-[(1S)-1-(2,3-dihydro-1-benzofuran-6-yl)propyl]-3-(4-oxopentyl)pyrrolidin-2-one
    —— ethane;3-(2-hydroxyphenyl)-3H-1-benzofuran-2-one —— C18H22O3
    ethane;3-(2-hydroxyphenyl)-3H-1-benzofuran-2-one
    —— (2Z)-7-chloro-2-(2-furylmethylene)-5-methyl-benzofuran-3-one oxime —— C14H10ClNO3
    (2Z)-7-chloro-2-(2-furylmethylene)-5-methyl-benzofuran-3-one oxime
    —— 3-[(6-Bromo-2,3-dihydro-1-benzofuran-5-yl)sulfanyl]propanoic acid —— C11H11BrO3S
    3-[(6-Bromo-2,3-dihydro-1-benzofuran-5-yl)sulfanyl]propanoic acid
    —— 4,6,7-Trimethyl-3-[4-(2-methylpropyl)phenyl]-2,3-dihydro-1-benzofuran-5-amine —— C21H27NO
    4,6,7-Trimethyl-3-[4-(2-methylpropyl)phenyl]-2,3-dihydro-1-benzofuran-5-amine
    —— (4E)-1-[3-(diethylamino)propyl]-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione —— C25H30N2O5
    (4E)-1-[3-(diethylamino)propyl]-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione
    —— 3-[6-[[(3R)-1-(2,3-dihydro-1-benzofuran-5-ylmethyl)pyrrolidin-3-yl]amino]pyridin-3-yl]-N-hydroxyprop-2-enamide —— C21H24N4O3
    3-[6-[[(3R)-1-(2,3-dihydro-1-benzofuran-5-ylmethyl)pyrrolidin-3-yl]amino]pyridin-3-yl]-N-hydroxyprop-2-enamide
    —— (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,3,5,6-tetramethylphenyl)methyl]dibenzofuran-4-carboxamide —— C28H29NO7
    (9aS)-8-acetyl-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxo-N-[(2,3,5,6-tetramethylphenyl)methyl]dibenzofuran-4-carboxamide
    —— 4-(2,2-Dimethylpropyl)-7-methyl-2,3-dihydro-1-benzofuran —— C14H20O
    4-(2,2-Dimethylpropyl)-7-methyl-2,3-dihydro-1-benzofuran
    —— 7-bromo-3,3-dimethyl-5-prop-1-enyl-2H-1-benzofuran —— C13H15BrO
    7-bromo-3,3-dimethyl-5-prop-1-enyl-2H-1-benzofuran
    —— 9b-ethyl-1,6-dihydroxy-9-methyl-1-[1-(methylamino)ethyl]-4aH-dibenzofuran-4-one —— C18H23NO4
    9b-ethyl-1,6-dihydroxy-9-methyl-1-[1-(methylamino)ethyl]-4aH-dibenzofuran-4-one
    —— (4E)-1-[2-(diethylamino)ethyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione —— C24H28N2O4S
    (4E)-1-[2-(diethylamino)ethyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 3-[4-(3-butoxy-2-hydroxypropoxy)-3-methylphenyl]-5-cyclohexyl-3H-1-benzofuran-2-one;[4-(5-butyl-2-oxo-3H-1-benzofuran-3-yl)phenyl] N-[6-[[4-(5-butyl-2,3-dihydro-1-benzofuran-3-yl)benzoyl]amino]-2,4,4-trimethylhexyl]carbamate;3-(4-methylphenyl)-5-piperidin-1-yl-3H-1-benzofuran-2-one —— C95H113N3O13
    3-[4-(3-butoxy-2-hydroxypropoxy)-3-methylphenyl]-5-cyclohexyl-3H-1-benzofuran-2-one;[4-(5-butyl-2-oxo-3H-1-benzofuran-3-yl)phenyl] N-[6-[[4-(5-butyl-2,3-dihydro-1-benzofuran-3-yl)benzoyl]amino]-2,4,4-trimethylhexyl]carbamate;3-(4-methylphenyl)-5-piperidin-1-yl-3H-1-benzofuran-2-one
    —— [7-(2,4-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl N-benzylcarbamate —— C24H21Cl2NO3
    [7-(2,4-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl N-benzylcarbamate
    —— 5-[[3-[3,3-dimethyl-5-(1,3-oxazol-2-yl)-2H-1-benzofuran-7-yl]-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione —— C24H17F3N2O5S
    5-[[3-[3,3-dimethyl-5-(1,3-oxazol-2-yl)-2H-1-benzofuran-7-yl]-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
    —— 1-[7-(4-Methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C17H19NO2
    1-[7-(4-Methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— 4-Ethoxy-3-phenyl-2,3-dihydro-1-benzofuran —— C16H16O2
    4-Ethoxy-3-phenyl-2,3-dihydro-1-benzofuran
    —— 3-hydroxy-1-(3-methoxypropyl)-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-5-(5-methylfuran-2-yl)-2,5-dihydro-1H-pyrrol-2-one —— C23H25NO6
    3-hydroxy-1-(3-methoxypropyl)-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-5-(5-methylfuran-2-yl)-2,5-dihydro-1H-pyrrol-2-one
    —— (4E)-5-(furan-2-yl)-4-[hydroxy(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-phenylethyl)pyrrolidine-2,3-dione —— C26H23NO5
    (4E)-5-(furan-2-yl)-4-[hydroxy(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-phenylethyl)pyrrolidine-2,3-dione
    —— N-(10-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrimido[1,2-a]azepin-10-yl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C23H23N5O3
    N-(10-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrimido[1,2-a]azepin-10-yl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2-Methyl-3a,8b-diphenyl-1-prop-1-enylfuro[2,3-b][1]benzofuran-6-yl) trifluoromethanesulfonate —— C27H21F3O5S
    (2-Methyl-3a,8b-diphenyl-1-prop-1-enylfuro[2,3-b][1]benzofuran-6-yl) trifluoromethanesulfonate
    —— (9aS)-8-acetyl-N-[(4-fluoro-2,6-dimethylphenyl)methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide —— C26H24FNO7
    (9aS)-8-acetyl-N-[(4-fluoro-2,6-dimethylphenyl)methyl]-1-hydroxy-3-methoxy-9a-methyl-7,9-dioxodibenzofuran-4-carboxamide
    —— 3-(3,4-dimethylphenyl)-5-ethenyl-3H-1-benzofuran-2-one;2-(2-methylprop-2-enoyloxy)ethyl 3-(5,7-dimethyl-2-oxo-3H-1-benzofuran-3-yl)benzoate —— C41H38O8
    3-(3,4-dimethylphenyl)-5-ethenyl-3H-1-benzofuran-2-one;2-(2-methylprop-2-enoyloxy)ethyl 3-(5,7-dimethyl-2-oxo-3H-1-benzofuran-3-yl)benzoate
    —— (7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran-2-yl) N-benzyl-N-methylcarbamate —— C21H24ClNO3
    (7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran-2-yl) N-benzyl-N-methylcarbamate
    —— 1-[[5-Fluoro-7-(2-methoxy-5-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[[5-fluoro-7-(5-methoxy-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]hydrazine —— C34H34F2N2O4
    1-[[5-Fluoro-7-(2-methoxy-5-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[[5-fluoro-7-(5-methoxy-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]hydrazine
    —— 11-Amino-6,12-dimethyl-13-(2-methylpropyl)-2-oxa-10-azahexacyclo[13.9.1.01,9.03,8.09,14.017,22]pentacosa-3(8),4,6,10,14,17,19,21-octaen-16-ol —— C29H34N2O2
    11-Amino-6,12-dimethyl-13-(2-methylpropyl)-2-oxa-10-azahexacyclo[13.9.1.01,9.03,8.09,14.017,22]pentacosa-3(8),4,6,10,14,17,19,21-octaen-16-ol
    —— [(1R,2R,3aS,8bS)-5-butyl-1-[(E,3R)-4-methyl-4-phenoxy-3-phosphanyloxypent-1-enyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-yl]oxy-tritiophosphane —— C27H36O4P2
    [(1R,2R,3aS,8bS)-5-butyl-1-[(E,3R)-4-methyl-4-phenoxy-3-phosphanyloxypent-1-enyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-yl]oxy-tritiophosphane