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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
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(pyridin-3-ylmethyl)cyclopropanamine —— C18H20N2O
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(pyridin-3-ylmethyl)cyclopropanamine
    —— 3-[cyclopropylmethyl(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H34N2O8
    3-[cyclopropylmethyl(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione —— C25H21N3O4
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-4-ylmethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C24H20N2O4S
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-4-ylmethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 1-(Furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-ylpyrrolidine-2,3-dione —— C24H20N2O5
    1-(Furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— 5-(Furan-2-yl)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione —— C23H19NO6
    5-(Furan-2-yl)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione
    —— 5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione —— C24H20N2O5
    5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione —— C25H21N3O4
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione
    —— Prop-2-enyl 2-[2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C26H22N2O7S
    Prop-2-enyl 2-[2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— Prop-2-enyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C27H23N3O6S
    Prop-2-enyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— Prop-2-enyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C26H22N2O6S2
    Prop-2-enyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— Ethyl 2-[2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C25H22N2O7S
    Ethyl 2-[2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— Ethyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C26H23N3O6S
    Ethyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— Ethyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C25H22N2O6S2
    Ethyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— Methyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C25H21N3O6S
    Methyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— Methyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C24H20N2O6S2
    Methyl 2-[4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— [1-[2-(diethylazaniumyl)ethyl]-4,5-dioxo-2-pyridin-4-ylpyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate —— C25H29N3O4
    [1-[2-(diethylazaniumyl)ethyl]-4,5-dioxo-2-pyridin-4-ylpyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate
    —— 5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-morpholin-4-ylethyl)pyrrolidine-2,3-dione —— C24H26N2O6
    5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-morpholin-4-ylethyl)pyrrolidine-2,3-dione
    —— (2R)-N-[3-(cyclopropylamino)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H20N2O2
    (2R)-N-[3-(cyclopropylamino)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[3-(cyclopropylamino)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H20N2O2
    (2S)-N-[3-(cyclopropylamino)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)pyrrolidine-2,3-dione —— C25H28N2O6
    5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)pyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C25H28N2O5S
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)pyrrolidine-2,3-dione —— C22H23NO6
    5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)pyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione —— C23H24N2O5
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— 5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)pyrrolidine-2,3-dione —— C21H21NO6
    5-(Furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)pyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-pyridin-4-ylpyrrolidine-2,3-dione —— C22H22N2O5
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C21H21NO5S
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 1-[3-(Dimethylamino)propyl]-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione —— C23H26N2O5
    1-[3-(Dimethylamino)propyl]-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione
    —— 1-[3-(Dimethylamino)propyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione —— C23H26N2O4S
    1-[3-(Dimethylamino)propyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-pyridin-2-yl-5-pyridin-4-ylpyrrolidine-2,3-dione —— C24H19N3O4
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-pyridin-2-yl-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— 4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-pyridin-2-yl-5-thiophen-2-ylpyrrolidine-2,3-dione —— C23H18N2O4S
    4-[Hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-pyridin-2-yl-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— (3R)-5-phenyl-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine —— C17H19NO
    (3R)-5-phenyl-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine
    —— (3S)-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-amine —— C10H13NO3
    (3S)-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-amine
    —— (3R)-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-amine —— C10H13NO3
    (3R)-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-amine
    —— 3-[acetyl(benzyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H28N2O7
    3-[acetyl(benzyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-cyclopentylpropanoyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H38N2O8
    3-[3-cyclopentylpropanoyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-1-(methylamino)propan-2-ol —— C12H17NO2
    (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-1-(methylamino)propan-2-ol
    —— (2R)-1-amino-2-(2,3-dihydro-1-benzofuran-5-yl)propan-2-ol —— C11H15NO2
    (2R)-1-amino-2-(2,3-dihydro-1-benzofuran-5-yl)propan-2-ol
    —— (2S)-1-amino-2-(2,3-dihydro-1-benzofuran-5-yl)propan-2-ol —— C11H15NO2
    (2S)-1-amino-2-(2,3-dihydro-1-benzofuran-5-yl)propan-2-ol
    —— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-1-(methylamino)propan-2-ol —— C12H17NO2
    (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-1-(methylamino)propan-2-ol
    —— (2S)-5-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H16ClNO3
    (2S)-5-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 3-[cyclobutanecarbonyl-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H31FN2O7
    3-[cyclobutanecarbonyl-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-ethoxyacetyl)-(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H35N3O7
    3-[(2-ethoxyacetyl)-(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentanecarbonyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H37N3O6
    3-[cyclopentanecarbonyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopropylmethyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O8
    3-[cyclopropylmethyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[hexyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O6
    3-[hexyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-(3-methoxyphenyl)ethyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H32N2O6
    4-hydroxy-N-(2-hydroxyethyl)-3-[2-(3-methoxyphenyl)ethyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2R,3R)-2,3-dimethyl-N-[3-[(1S)-1-phenylethoxy]propyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C22H27NO3
    (2R,3R)-2,3-dimethyl-N-[3-[(1S)-1-phenylethoxy]propyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-2,3-dimethyl-N-[3-[(1S)-1-phenylethoxy]propyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C22H27NO3
    (2S,3R)-2,3-dimethyl-N-[3-[(1S)-1-phenylethoxy]propyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-N-[(2R)-2-(4-ethoxy-3-methoxyphenyl)-2-morpholin-4-ylethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C26H34N2O5
    (2S,3R)-N-[(2R)-2-(4-ethoxy-3-methoxyphenyl)-2-morpholin-4-ylethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide