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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-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(R)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea —— C22H24N4O3
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(R)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(5-morpholin-4-ylsulfonylthiophen-2-yl)methyl]urea —— C19H23N3O5S2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(5-morpholin-4-ylsulfonylthiophen-2-yl)methyl]urea
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(S)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea —— C22H24N4O3
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(S)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(5-morpholin-4-ylsulfonylthiophen-2-yl)methyl]urea —— C19H23N3O5S2
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(5-morpholin-4-ylsulfonylthiophen-2-yl)methyl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(R)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea —— C22H24N4O3
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(R)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(S)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea —— C22H24N4O3
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(S)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]urea
    —— 1-[2-[4-(difluoromethoxy)phenyl]ethyl]-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]urea —— C19H20F2N2O3
    1-[2-[4-(difluoromethoxy)phenyl]ethyl]-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]urea
    —— (2R,5S)-4-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-2,5-dimethylmorpholine —— C14H19NO4S
    (2R,5S)-4-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-2,5-dimethylmorpholine
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,5-dimethyl-1-(thiophen-2-ylmethyl)pyrrole-3-carboxamide —— C21H22N2O2S
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,5-dimethyl-1-(thiophen-2-ylmethyl)pyrrole-3-carboxamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,5-dimethyl-1-(thiophen-2-ylmethyl)pyrrole-3-carboxamide —— C21H22N2O2S
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,5-dimethyl-1-(thiophen-2-ylmethyl)pyrrole-3-carboxamide
    —— (5Z)-5-[[4-[[(2S)-1-[(2,2,4,6,7-pentamethyl-5-phenylmethoxy-3H-1-benzofuran-3-yl)methyl]pyrrolidin-2-yl]methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione —— C36H40N2O5S
    (5Z)-5-[[4-[[(2S)-1-[(2,2,4,6,7-pentamethyl-5-phenylmethoxy-3H-1-benzofuran-3-yl)methyl]pyrrolidin-2-yl]methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione
    —— 2,2,4,5,7,7-hexamethyl-1-(4-methylphenyl)-6,8-dihydro-1H-furo[3,2-e]indole —— C23H29NO
    2,2,4,5,7,7-hexamethyl-1-(4-methylphenyl)-6,8-dihydro-1H-furo[3,2-e]indole
    —— (1S,2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-(2-fluorophenyl)cyclopropane-1-carboxamide —— C22H24FNO3
    (1S,2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-(2-fluorophenyl)cyclopropane-1-carboxamide
    —— (1R,2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-(2-fluorophenyl)cyclopropane-1-carboxamide —— C22H24FNO3
    (1R,2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-(2-fluorophenyl)cyclopropane-1-carboxamide
    —— N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-[(3R)-1,1-dioxothiolan-3-yl]acetamide —— C18H25NO5S
    N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-[(3R)-1,1-dioxothiolan-3-yl]acetamide
    —— (1R,2S)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-(2-fluorophenyl)cyclopropane-1-carboxamide —— C22H24FNO3
    (1R,2S)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-(2-fluorophenyl)cyclopropane-1-carboxamide
    —— N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-[(3S)-1,1-dioxothiolan-3-yl]acetamide —— C18H25NO5S
    N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-[(3S)-1,1-dioxothiolan-3-yl]acetamide
    —— (2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2,3-dihydro-1-benzothiophene-2-carboxamide —— C21H23NO3S
    (2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2,3-dihydro-1-benzothiophene-2-carboxamide
    —— (2S)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2,3-dihydro-1-benzothiophene-2-carboxamide —— C21H23NO3S
    (2S)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2,3-dihydro-1-benzothiophene-2-carboxamide
    —— (2S)-5-chloro-N-[[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H14ClF3N2O3
    (2S)-5-chloro-N-[[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H14ClF3N2O3
    (2R)-5-chloro-N-[[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (5S,7S)-3-bromo-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]adamantane-1-carboxamide —— C20H24BrNO2
    (5S,7S)-3-bromo-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]adamantane-1-carboxamide
    —— (5S,7S)-3-bromo-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]adamantane-1-carboxamide —— C20H24BrNO2
    (5S,7S)-3-bromo-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]adamantane-1-carboxamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(3,4,5-trimethoxyphenyl)propanamide —— C21H25NO5
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(3,4,5-trimethoxyphenyl)propanamide
    —— 2-(4-bromophenoxy)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C17H16BrNO3
    2-(4-bromophenoxy)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— (E)-3-(1-benzyl-5-chloro-3-methylpyrazol-4-yl)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide —— C23H22ClN3O2
    (E)-3-(1-benzyl-5-chloro-3-methylpyrazol-4-yl)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide
    —— (3R)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide —— C19H21BrN2O4S2
    (3R)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(4-fluorophenyl)-4-methyl-1,3-thiazole-5-carboxamide —— C20H17FN2O2S
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(4-fluorophenyl)-4-methyl-1,3-thiazole-5-carboxamide
    —— (E)-3-(1-benzyl-5-chloro-3-methylpyrazol-4-yl)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide —— C23H22ClN3O2
    (E)-3-(1-benzyl-5-chloro-3-methylpyrazol-4-yl)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide
    —— (3R)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide —— C19H21BrN2O4S2
    (3R)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide
    —— (3S)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide —— C19H21BrN2O4S2
    (3S)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide
    —— 2-(4-bromophenoxy)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C17H16BrNO3
    2-(4-bromophenoxy)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— (3S)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide —— C19H21BrN2O4S2
    (3S)-1-(5-bromothiophen-2-yl)sulfonyl-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-3-carboxamide
    —— (3S)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-5-oxo-1-propan-2-ylpyrrolidine-3-carboxamide —— C19H21N3O3S
    (3S)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-5-oxo-1-propan-2-ylpyrrolidine-3-carboxamide
    —— (3R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-5-oxo-1-propan-2-ylpyrrolidine-3-carboxamide —— C19H21N3O3S
    (3R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-5-oxo-1-propan-2-ylpyrrolidine-3-carboxamide
    —— [(2R)-1-(4-benzylpiperazin-1-yl)-1-oxopropan-2-yl] 2,3-dihydro-1-benzofuran-5-carboxylate —— C23H26N2O4
    [(2R)-1-(4-benzylpiperazin-1-yl)-1-oxopropan-2-yl] 2,3-dihydro-1-benzofuran-5-carboxylate
    —— [2-[1-[(2S)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]-2-oxoethyl] 2,3-dihydro-1-benzofuran-5-carboxylate —— C21H25NO5
    [2-[1-[(2S)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]-2-oxoethyl] 2,3-dihydro-1-benzofuran-5-carboxylate
    —— [2-[[(1R)-3-methyl-1-phenylbutyl]amino]-2-oxoethyl] 2,3-dihydro-1-benzofuran-5-carboxylate —— C22H25NO4
    [2-[[(1R)-3-methyl-1-phenylbutyl]amino]-2-oxoethyl] 2,3-dihydro-1-benzofuran-5-carboxylate
    —— methyl 5-[(2S)-2-(2,3-dihydro-1-benzofuran-5-carbonyloxy)propanoyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate —— C20H21NO6
    methyl 5-[(2S)-2-(2,3-dihydro-1-benzofuran-5-carbonyloxy)propanoyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate
    —— [(2S)-1-(4-benzylpiperazin-1-yl)-1-oxopropan-2-yl] 2,3-dihydro-1-benzofuran-5-carboxylate —— C23H26N2O4
    [(2S)-1-(4-benzylpiperazin-1-yl)-1-oxopropan-2-yl] 2,3-dihydro-1-benzofuran-5-carboxylate
    —— methyl 5-[(2R)-2-(2,3-dihydro-1-benzofuran-5-carbonyloxy)propanoyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate —— C20H21NO6
    methyl 5-[(2R)-2-(2,3-dihydro-1-benzofuran-5-carbonyloxy)propanoyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate
    —— [2-[1-[(2R)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]-2-oxoethyl] 2,3-dihydro-1-benzofuran-5-carboxylate —— C21H25NO5
    [2-[1-[(2R)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]-2-oxoethyl] 2,3-dihydro-1-benzofuran-5-carboxylate
    —— (2S)-N-[(5-bromo-2-fluorophenyl)methyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H12BrClFNO2
    (2S)-N-[(5-bromo-2-fluorophenyl)methyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(5-bromo-2-fluorophenyl)methyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H12BrClFNO2
    (2R)-N-[(5-bromo-2-fluorophenyl)methyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(1R)-1-(4-cyanophenyl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-ethylacetamide —— C23H26N2O3
    N-[(1R)-1-(4-cyanophenyl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-ethylacetamide
    —— N-[(1R)-1-(2,4-dichlorophenyl)ethyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-N-methylacetamide —— C19H19Cl2NO2
    N-[(1R)-1-(2,4-dichlorophenyl)ethyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-N-methylacetamide
    —— N-[(1S)-1-(2,4-dichlorophenyl)ethyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-N-methylacetamide —— C19H19Cl2NO2
    N-[(1S)-1-(2,4-dichlorophenyl)ethyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-N-methylacetamide
    —— (2S)-5-chloro-N-[(1R)-1-(4-propan-2-yloxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H22ClNO3
    (2S)-5-chloro-N-[(1R)-1-(4-propan-2-yloxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N'-[(2S)-2-(2,3-dimethylphenoxy)propanoyl]-2,3-dihydro-1-benzofuran-5-carbohydrazide —— C20H22N2O4
    N'-[(2S)-2-(2,3-dimethylphenoxy)propanoyl]-2,3-dihydro-1-benzofuran-5-carbohydrazide
    —— N'-[(2R)-2-(2,3-dimethylphenoxy)propanoyl]-2,3-dihydro-1-benzofuran-5-carbohydrazide —— C20H22N2O4
    N'-[(2R)-2-(2,3-dimethylphenoxy)propanoyl]-2,3-dihydro-1-benzofuran-5-carbohydrazide