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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
    —— (2S)-N-[(1-benzylimidazol-2-yl)methyl]-7-chloro-2-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide —— C20H20ClN3O3S
    (2S)-N-[(1-benzylimidazol-2-yl)methyl]-7-chloro-2-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (2R)-N-[(1-benzylimidazol-2-yl)methyl]-7-chloro-2-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide —— C20H20ClN3O3S
    (2R)-N-[(1-benzylimidazol-2-yl)methyl]-7-chloro-2-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— [(3R)-2,3-dihydro-1-benzofuran-3-yl]-(6-methyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-1-yl)methanone —— C17H16N2O3
    [(3R)-2,3-dihydro-1-benzofuran-3-yl]-(6-methyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-1-yl)methanone
    —— (4aR,5S,7aR)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine —— C16H21NOS2
    (4aR,5S,7aR)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine
    —— (4aR,5R,7aR)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine —— C16H21NOS2
    (4aR,5R,7aR)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine
    —— (4aR,5S,7aR)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine —— C16H21NOS2
    (4aR,5S,7aR)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine
    —— (4aR,5R,7aR)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine —— C16H21NOS2
    (4aR,5R,7aR)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]dithiin-5-amine
    —— [(3S)-2,3-dihydro-1-benzofuran-3-yl]-(6-methyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-1-yl)methanone —— C17H16N2O3
    [(3S)-2,3-dihydro-1-benzofuran-3-yl]-(6-methyl-2,3-dihydropyrido[2,3-b][1,4]oxazin-1-yl)methanone
    —— [(3R)-1-methyl-5-oxopyrrolidin-3-yl]methyl 2,3-dihydro-1-benzofuran-5-carboxylate —— C15H17NO4
    [(3R)-1-methyl-5-oxopyrrolidin-3-yl]methyl 2,3-dihydro-1-benzofuran-5-carboxylate
    —— [(3S)-1-methyl-5-oxopyrrolidin-3-yl]methyl 2,3-dihydro-1-benzofuran-5-carboxylate —— C15H17NO4
    [(3S)-1-methyl-5-oxopyrrolidin-3-yl]methyl 2,3-dihydro-1-benzofuran-5-carboxylate
    —— (2S)-N-[2-[(2-chloropyridin-4-yl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H17ClN2O2S
    (2S)-N-[2-[(2-chloropyridin-4-yl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-3-methylsulfanylpyrazole-4-carboxamide —— C17H21N3O3S
    N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-3-methylsulfanylpyrazole-4-carboxamide
    —— (2R)-N-[2-[(2-chloropyridin-4-yl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H17ClN2O2S
    (2R)-N-[2-[(2-chloropyridin-4-yl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-3-methylsulfanylpyrazole-4-carboxamide —— C17H21N3O3S
    N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-3-methylsulfanylpyrazole-4-carboxamide
    —— 4-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]benzonitrile —— C18H18N2O2
    4-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]benzonitrile
    —— 4-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]benzonitrile —— C18H18N2O2
    4-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]benzonitrile
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-[(dimethylamino)methyl]-1,2-oxazole-3-carboxamide —— C16H19N3O3
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-[(dimethylamino)methyl]-1,2-oxazole-3-carboxamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-[(dimethylamino)methyl]-1,2-oxazole-3-carboxamide —— C16H19N3O3
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-[(dimethylamino)methyl]-1,2-oxazole-3-carboxamide
    —— (2R)-N-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-(4-methyl-1,2,4-triazol-3-yl)pyrrolidine-1-carboxamide —— C18H23N5O2
    (2R)-N-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-(4-methyl-1,2,4-triazol-3-yl)pyrrolidine-1-carboxamide
    —— (2S)-N-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-(4-methyl-1,2,4-triazol-3-yl)pyrrolidine-1-carboxamide —— C18H23N5O2
    (2S)-N-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-(4-methyl-1,2,4-triazol-3-yl)pyrrolidine-1-carboxamide
    —— (2R)-5-fluoro-N-[2-[(4-methyl-2-oxo-3H-1,3-thiazol-5-yl)sulfonylamino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H16FN3O5S2
    (2R)-5-fluoro-N-[2-[(4-methyl-2-oxo-3H-1,3-thiazol-5-yl)sulfonylamino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-fluoro-N-[2-[(4-methyl-2-oxo-3H-1,3-thiazol-5-yl)sulfonylamino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H16FN3O5S2
    (2S)-5-fluoro-N-[2-[(4-methyl-2-oxo-3H-1,3-thiazol-5-yl)sulfonylamino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (5R)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione —— C25H21NO5
    (5R)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione
    —— (5E)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H19NO3S2
    (5E)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (1R,3R)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol —— C17H21NO2S
    (1R,3R)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol
    —— (1R,3S)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol —— C17H21NO2S
    (1R,3S)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol
    —— (1S,3S)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol —— C17H21NO2S
    (1S,3S)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol
    —— (1S,3R)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol —— C17H21NO2S
    (1S,3R)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-1-thiophen-2-ylbutan-1-ol
    —— [(2R)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C18H20FN3O2
    [(2R)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2R)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C18H20FN3O2
    [(2R)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2S)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C18H20FN3O2
    [(2S)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2S)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C18H20FN3O2
    [(2S)-2-(3,5-dimethyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— (5E)-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[(1R)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C21H19NO2S2
    (5E)-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[(1R)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-(2-morpholin-4-ylethyl)pyrazol-4-amine —— C20H28N4O3
    N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-(2-morpholin-4-ylethyl)pyrazol-4-amine
    —— N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-(2-morpholin-4-ylethyl)pyrazol-4-amine —— C20H28N4O3
    N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-(2-morpholin-4-ylethyl)pyrazol-4-amine
    —— ethyl (2S)-5-[(5-bromo-3-fluoropyridin-2-yl)sulfamoyl]-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H14BrFN2O5S
    ethyl (2S)-5-[(5-bromo-3-fluoropyridin-2-yl)sulfamoyl]-2,3-dihydro-1-benzofuran-2-carboxylate
    —— ethyl (2R)-5-[(5-bromo-3-fluoropyridin-2-yl)sulfamoyl]-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H14BrFN2O5S
    ethyl (2R)-5-[(5-bromo-3-fluoropyridin-2-yl)sulfamoyl]-2,3-dihydro-1-benzofuran-2-carboxylate
    —— 2,6-dichloro-4-[(1R)-1-(2,3-dihydro-1-benzofuran-5-ylmethylamino)ethyl]aniline —— C17H18Cl2N2O
    2,6-dichloro-4-[(1R)-1-(2,3-dihydro-1-benzofuran-5-ylmethylamino)ethyl]aniline
    —— 2,6-dichloro-4-[(1S)-1-(2,3-dihydro-1-benzofuran-5-ylmethylamino)ethyl]aniline —— C17H18Cl2N2O
    2,6-dichloro-4-[(1S)-1-(2,3-dihydro-1-benzofuran-5-ylmethylamino)ethyl]aniline
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]cyclopentanecarboxamide —— C18H25NO3
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]cyclopentanecarboxamide
    —— 2-(4-chloro-2-methylphenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C21H24ClNO4
    2-(4-chloro-2-methylphenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-(2-chlorophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H22ClNO4
    2-(2-chlorophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— (3S)-5-bromo-N-(cyclopropylmethyl)-N-(2-hydroxyethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H18BrNO3
    (3S)-5-bromo-N-(cyclopropylmethyl)-N-(2-hydroxyethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-phenylpropanamide —— C21H25NO3
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-phenylpropanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenoxyacetamide —— C20H23NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenoxyacetamide
    —— (3R)-5-bromo-N-(cyclopropylmethyl)-N-(2-hydroxyethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H18BrNO3
    (3R)-5-bromo-N-(cyclopropylmethyl)-N-(2-hydroxyethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 5-(difluoromethyl)-N-[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]-1-(2-methylpropyl)pyrazole-4-carboxamide —— C18H21F2N3O2
    5-(difluoromethyl)-N-[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]-1-(2-methylpropyl)pyrazole-4-carboxamide
    —— (3S)-5-bromo-N-(3-methyl-1,2,4-thiadiazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C12H10BrN3O2S
    (3S)-5-bromo-N-(3-methyl-1,2,4-thiadiazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-[(1S)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H17BrN2O2
    (3R)-5-bromo-N-[(1S)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-[(1-methylpyrrol-3-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H15BrN2O2
    (3R)-5-bromo-N-[(1-methylpyrrol-3-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide