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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]-N-[(4-ethoxy-3-methoxyphenyl)methyl]methanamine —— C19H23NO3
    1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(4-ethoxy-3-methoxyphenyl)methyl]methanamine
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(3-methoxypropyl)-1,2,4-triazole —— C18H25N3O3S
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(3-methoxypropyl)-1,2,4-triazole
    —— N-cyclopentyl-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3,4-dihydro-2H-pyran-6-carboxamide —— C20H25NO3
    N-cyclopentyl-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3,4-dihydro-2H-pyran-6-carboxamide
    —— methyl (2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate —— C12H14O3
    methyl (2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate
    —— methyl (2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate —— C12H14O3
    methyl (2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate
    —— (2R)-5-fluoro-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H19FN4O2
    (2R)-5-fluoro-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3S)-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H20N4O2
    (3S)-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (2S)-5-fluoro-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H19FN4O2
    (2S)-5-fluoro-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3R)-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H20N4O2
    (3R)-N-[2-(3-propan-2-yl-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 7-[[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]amino]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one —— C18H19N3O3S
    7-[[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]amino]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one
    —— 7-[[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]amino]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one —— C18H19N3O3S
    7-[[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]amino]methyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one
    —— (1S)-2,2-dichloro-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylcyclopropane-1-carboxamide —— C16H19Cl2NO3
    (1S)-2,2-dichloro-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylcyclopropane-1-carboxamide
    —— (1R)-2,2-dichloro-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylcyclopropane-1-carboxamide —— C16H19Cl2NO3
    (1R)-2,2-dichloro-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylcyclopropane-1-carboxamide
    —— (1R)-2,2-dichloro-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylcyclopropane-1-carboxamide —— C16H19Cl2NO3
    (1R)-2,2-dichloro-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylcyclopropane-1-carboxamide
    —— (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine —— C16H23NO4S
    (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine
    —— (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine —— C16H23NO4S
    (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine
    —— (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine —— C16H23NO4S
    (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine
    —— (1S,2R,4R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide —— C18H18N2O3S
    (1S,2R,4R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide
    —— (1S,2S,4R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide —— C18H18N2O3S
    (1S,2S,4R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-7-oxabicyclo[2.2.1]heptane-2-carboxamide
    —— N-[(2S)-2-(dimethylamino)-2-phenylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C18H22N2O3S
    N-[(2S)-2-(dimethylamino)-2-phenylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(2R)-2-(dimethylamino)-2-phenylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C18H22N2O3S
    N-[(2R)-2-(dimethylamino)-2-phenylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-cyclopentyl-2-[5-[(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-1,2,4-oxadiazol-3-yl]acetamide —— C19H23N3O3
    N-cyclopentyl-2-[5-[(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-1,2,4-oxadiazol-3-yl]acetamide
    —— N-cyclopentyl-2-[5-[(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-1,2,4-oxadiazol-3-yl]acetamide —— C19H23N3O3
    N-cyclopentyl-2-[5-[(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-1,2,4-oxadiazol-3-yl]acetamide
    —— N-cyclopentyl-2-[5-[(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-1,2,4-oxadiazol-3-yl]acetamide —— C19H23N3O3
    N-cyclopentyl-2-[5-[(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-1,2,4-oxadiazol-3-yl]acetamide
    —— (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H23NO4
    (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 3-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C24H35N3O3
    3-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[5-(phenoxymethyl)tetrazol-2-yl]acetamide —— C22H25N5O4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[5-(phenoxymethyl)tetrazol-2-yl]acetamide
    —— (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide —— C17H22F3NO4
    (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide
    —— ethyl 4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-4-oxobutanoate —— C18H25NO5
    ethyl 4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-4-oxobutanoate
    —— 3-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C24H35N3O3
    3-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-methylthiadiazole-5-carboxamide —— C16H19N3O3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-methylthiadiazole-5-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-methylthiadiazole-5-carboxamide —— C16H19N3O3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-methylthiadiazole-5-carboxamide
    —— (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide —— C17H22F3NO4
    (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide
    —— (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide —— C17H23NO5S
    (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide
    —— (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H23NO4
    (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 4-acetyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1H-pyrrole-2-carboxamide —— C19H22N2O4
    4-acetyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1H-pyrrole-2-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)propanamide —— C21H23N3O4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)propanamide
    —— (E)-3-(1-benzyltriazol-4-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide —— C24H26N4O3
    (E)-3-(1-benzyltriazol-4-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-methyl-4-oxo-1-phenylpyridazine-3-carboxamide —— C24H25N3O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-methyl-4-oxo-1-phenylpyridazine-3-carboxamide
    —— (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide —— C17H23NO5S
    (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)propanamide —— C21H23N3O4S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)propanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[5-(phenoxymethyl)tetrazol-2-yl]acetamide —— C22H25N5O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[5-(phenoxymethyl)tetrazol-2-yl]acetamide
    —— 4-acetyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1H-pyrrole-2-carboxamide —— C19H22N2O4
    4-acetyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1H-pyrrole-2-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propanamide —— C24H27N3O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propanamide
    —— (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide —— C17H22F3NO4
    (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-3-yl-1,2,4-oxadiazol-5-yl)propanamide —— C21H23N3O4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-3-yl-1,2,4-oxadiazol-5-yl)propanamide
    —— (2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H23NO4
    (2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (E)-3-(1-benzylpyrazol-4-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide —— C25H27N3O3
    (E)-3-(1-benzylpyrazol-4-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide
    —— 2-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C23H33N3O3
    2-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C23H33N3O3
    2-[3,5-dimethyl-1-(2-methylpropyl)pyrazol-4-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide