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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
    —— (2R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine —— C15H23NO2
    (2R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanylmethyl]-4,5-dimethyl-1,2,4-triazole —— C17H23N3O2S
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanylmethyl]-4,5-dimethyl-1,2,4-triazole
    —— (2S)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine —— C15H23NO2
    (2S)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine
    —— N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine —— C19H25N3OS
    N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine
    —— (3R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine —— C16H21F3N2O
    (3R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine
    —— (3R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine —— C16H21F3N2O
    (3R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine
    —— N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine —— C19H25N3OS
    N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine
    —— (4R)-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine —— C18H23N3O
    (4R)-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine
    —— (4R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine —— C18H23N3O
    (4R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine
    —— (4R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine —— C18H23N3O
    (4R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine
    —— N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(pyridin-4-ylmethyl)piperidin-4-amine —— C21H27N3O
    N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(pyridin-4-ylmethyl)piperidin-4-amine
    —— N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(pyridin-4-ylmethyl)piperidin-4-amine —— C21H27N3O
    N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(pyridin-4-ylmethyl)piperidin-4-amine
    —— (4R)-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine —— C18H23N3O
    (4R)-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-methyl-4,5,6,7-tetrahydroindazol-4-amine
    —— N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine —— C19H25N3OS
    N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine
    —— N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-pyridin-2-ylpiperidin-4-amine —— C20H25N3O
    N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-pyridin-2-ylpiperidin-4-amine
    —— (3R)-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine —— C16H21F3N2O
    (3R)-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine
    —— N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-pyridin-2-ylpiperidin-4-amine —— C20H25N3O
    N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-pyridin-2-ylpiperidin-4-amine
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylimidazole —— C13H14N2O
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylimidazole
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylimidazole —— C13H14N2O
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylimidazole
    —— 5-bromo-1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridin-2-one —— C14H12BrNO2
    5-bromo-1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridin-2-one
    —— 5-bromo-1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridin-2-one —— C14H12BrNO2
    5-bromo-1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridin-2-one
    —— N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(pyridin-4-ylmethyl)piperidin-4-amine —— C21H27N3O
    N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(pyridin-4-ylmethyl)piperidin-4-amine
    —— (2R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine —— C15H23NO2
    (2R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine
    —— N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine —— C19H25N3OS
    N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(4-methyl-1,3-thiazol-2-yl)piperidin-4-amine
    —— (2S)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine —— C15H23NO2
    (2S)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-ethoxypropan-2-amine
    —— N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-pyridin-2-ylpiperidin-4-amine —— C20H25N3O
    N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-pyridin-2-ylpiperidin-4-amine
    —— N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-1-methylsulfonylpiperidine-4-carboxamide —— C17H24N2O5S
    N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-1-methylsulfonylpiperidine-4-carboxamide
    —— (3R)-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine —— C16H21F3N2O
    (3R)-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1-(2,2,2-trifluoroethyl)pyrrolidin-3-amine
    —— N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(4-methoxyphenyl)propanamide —— C20H23NO4
    N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(4-methoxyphenyl)propanamide
    —— N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-1-methylsulfonylpiperidine-4-carboxamide —— C17H24N2O5S
    N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-1-methylsulfonylpiperidine-4-carboxamide
    —— N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(4-methoxyphenyl)propanamide —— C20H23NO4
    N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(4-methoxyphenyl)propanamide
    —— N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]pent-4-enamide —— C15H19NO3
    N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]pent-4-enamide
    —— N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]pent-4-enamide —— C15H19NO3
    N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]pent-4-enamide
    —— diethyl-[2-[(5S)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]ethyl]azanium —— C24H29N2O4S+
    diethyl-[2-[(5S)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]ethyl]azanium
    —— 5-bromo-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]thiophene-2-sulfonamide —— C14H14BrNO4S2
    5-bromo-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]thiophene-2-sulfonamide
    —— diethyl-[2-[(5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]ethyl]azanium —— C24H29N2O4S+
    diethyl-[2-[(5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]ethyl]azanium
    —— 3-(2-chlorophenyl)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-5-methyl-1,2-oxazole-4-carboxamide —— C21H19ClN2O4
    3-(2-chlorophenyl)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-5-methyl-1,2-oxazole-4-carboxamide
    —— 2-[(5R)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]ethyl-dimethylazanium —— C22H25N2O4S+
    2-[(5R)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]ethyl-dimethylazanium
    —— 2-(4-chlorophenoxy)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-2-methylpropanamide —— C20H22ClNO4
    2-(4-chlorophenoxy)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-2-methylpropanamide
    —— 3-(2-chlorophenyl)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-5-methyl-1,2-oxazole-4-carboxamide —— C21H19ClN2O4
    3-(2-chlorophenyl)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-5-methyl-1,2-oxazole-4-carboxamide
    —— 5-bromo-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]thiophene-2-sulfonamide —— C14H14BrNO4S2
    5-bromo-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]thiophene-2-sulfonamide
    —— 2-(4-chlorophenoxy)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-2-methylpropanamide —— C20H22ClNO4
    2-(4-chlorophenoxy)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-2-methylpropanamide
    —— 1-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-(thiophen-2-ylmethyl)urea —— C18H23N3O2S
    1-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-(thiophen-2-ylmethyl)urea
    —— 5-bromo-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]thiophene-2-sulfonamide —— C16H19BrN2O3S2
    5-bromo-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]thiophene-2-sulfonamide
    —— N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-5-phenyl-1,2-oxazole-3-carboxamide —— C22H23N3O3
    N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-5-phenyl-1,2-oxazole-3-carboxamide
    —— methyl 3-[[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]sulfamoyl]thiophene-2-carboxylate —— C18H22N2O5S2
    methyl 3-[[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]sulfamoyl]thiophene-2-carboxylate
    —— N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]methanesulfonamide —— C13H20N2O3S
    N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]methanesulfonamide
    —— 1-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-[(4-fluorophenyl)methyl]urea —— C20H24FN3O2
    1-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-[(4-fluorophenyl)methyl]urea
    —— 1-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-[(4-fluorophenyl)methyl]urea —— C20H24FN3O2
    1-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-[(4-fluorophenyl)methyl]urea
    —— N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)ethanesulfonamide —— C21H28N2O4S
    N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)ethanesulfonamide