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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-(3-methoxypyridin-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H14N2O3
    (2S)-N-(3-methoxypyridin-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(3-methoxypyridin-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H14N2O3
    (2R)-N-(3-methoxypyridin-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— tert-butyl N-[2-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-N-methylcarbamate —— C17H24N2O4
    tert-butyl N-[2-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-N-methylcarbamate
    —— tert-butyl N-[2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-N-methylcarbamate —— C17H24N2O4
    tert-butyl N-[2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-N-methylcarbamate
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2S)-4-methylmorpholin-2-yl]methanamine —— C15H22N2O2
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2S)-4-methylmorpholin-2-yl]methanamine
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2R)-4-methylmorpholin-2-yl]methanamine —— C15H22N2O2
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2R)-4-methylmorpholin-2-yl]methanamine
    —— (2S)-N-[2-(2-propan-2-yl-1,3-thiazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H20N2O2S
    (2S)-N-[2-(2-propan-2-yl-1,3-thiazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(1,5-dimethylpyrrol-2-yl)methyl]urea —— C17H21N3O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(1,5-dimethylpyrrol-2-yl)methyl]urea
    —— (2R)-N-[2-(2-propan-2-yl-1,3-thiazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H20N2O2S
    (2R)-N-[2-(2-propan-2-yl-1,3-thiazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-[(2R)-1-methylpyrrolidin-2-yl]pyrrolidin-1-yl]methanone —— C18H24N2O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-[(2R)-1-methylpyrrolidin-2-yl]pyrrolidin-1-yl]methanone
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-[(2S)-1-methylpyrrolidin-2-yl]pyrrolidin-1-yl]methanone —— C18H24N2O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-[(2S)-1-methylpyrrolidin-2-yl]pyrrolidin-1-yl]methanone
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(6-methylpyridazin-3-yl)-1,4-diazepan-1-yl]methanone —— C19H22N4O2
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(6-methylpyridazin-3-yl)-1,4-diazepan-1-yl]methanone
    —— (5R)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C22H23NO5S
    (5R)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— (5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C22H23NO5S
    (5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— diethyl-[2-[(2S)-2-(furan-2-yl)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium —— C24H29N2O5+
    diethyl-[2-[(2S)-2-(furan-2-yl)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium
    —— 3-[(5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]propyl-dimethylazanium —— C24H28N3O4+
    3-[(5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]propyl-dimethylazanium
    —— diethyl-[2-[(2R)-2-(furan-2-yl)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium —— C24H29N2O5+
    diethyl-[2-[(2R)-2-(furan-2-yl)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium
    —— diethyl-[2-[(2R)-2-(furan-2-yl)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium —— C24H29N2O5+
    diethyl-[2-[(2R)-2-(furan-2-yl)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium
    —— (5S)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C22H23NO5S
    (5S)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— (5S)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione —— C24H20N2O5
    (5S)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione
    —— (5R)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione —— C24H20N2O5
    (5R)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione
    —— (5R)-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione —— C24H20N2O5
    (5R)-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione
    —— [(2S)-1-[3-(dimethylazaniumyl)propyl]-4,5-dioxo-2-pyridin-4-ylpyrrolidin-3-ylidene]-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate —— C24H27N3O4
    [(2S)-1-[3-(dimethylazaniumyl)propyl]-4,5-dioxo-2-pyridin-4-ylpyrrolidin-3-ylidene]-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate
    —— diethyl-[2-[(2S)-2-(furan-2-yl)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium —— C24H29N2O5+
    diethyl-[2-[(2S)-2-(furan-2-yl)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4,5-dioxopyrrolidin-1-yl]ethyl]azanium
    —— (5S)-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione —— C24H20N2O5
    (5S)-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione
    —— (S)-ethofumesate —— C13H18O5S
    (S)-ethofumesate
    —— 3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propanoate —— C12H13O3-
    3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propanoate
    —— 3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propanoic acid —— C12H14O3
    3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propanoic acid
    —— (2S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-(4-methylpyrazol-1-yl)propan-2-amine —— C16H21N3O
    (2S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-(4-methylpyrazol-1-yl)propan-2-amine
    —— (2R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-(4-methylpyrazol-1-yl)propan-2-amine —— C16H21N3O
    (2R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-(4-methylpyrazol-1-yl)propan-2-amine
    —— (2S)-N-[2-(4-ethyl-5-methyl-1,3-thiazol-2-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H20N2O2S
    (2S)-N-[2-(4-ethyl-5-methyl-1,3-thiazol-2-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R,3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine —— C17H23N3O
    (2R,3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine
    —— (2S,3R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine —— C17H23N3O
    (2S,3R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine
    —— (2S,3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine —— C17H23N3O
    (2S,3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine
    —— (2R,3R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine —— C17H23N3O
    (2R,3R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-(4-methylpyrazol-1-yl)butan-2-amine
    —— N-[(2S)-2-(dimethylamino)-2-(4-ethylphenyl)ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C20H26N2O3S
    N-[(2S)-2-(dimethylamino)-2-(4-ethylphenyl)ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(2R)-2-(dimethylamino)-2-(4-ethylphenyl)ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C20H26N2O3S
    N-[(2R)-2-(dimethylamino)-2-(4-ethylphenyl)ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (2R)-5-chloro-N-(cyanomethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C11H9ClN2O2
    (2R)-5-chloro-N-(cyanomethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H22N2O3
    (2R)-N-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-1-[4-[[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol —— C20H32N2O3
    (2R)-1-[4-[[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol
    —— (2S)-1-[4-[[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol —— C20H32N2O3
    (2S)-1-[4-[[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol
    —— (2R)-1-[4-[[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol —— C20H32N2O3
    (2R)-1-[4-[[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol
    —— (2S)-1-[4-[[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol —— C20H32N2O3
    (2S)-1-[4-[[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylamino]methyl]piperidin-1-yl]propan-2-ol
    —— (2R)-5-chloro-N-(2-cyanoethyl)-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H15ClN2O3
    (2R)-5-chloro-N-(2-cyanoethyl)-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-(2-cyanoethyl)-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H15ClN2O3
    (2S)-5-chloro-N-(2-cyanoethyl)-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-[4-[[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol —— C19H30N2O3
    2-[4-[[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol
    —— 2-[4-[[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol —— C20H32N2O3
    2-[4-[[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol
    —— 2-[4-[[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol —— C20H32N2O3
    2-[4-[[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol
    —— 2-[4-[[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol —— C19H30N2O3
    2-[4-[[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methyl]piperidin-1-yl]ethanol
    —— (2R,3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-pyrazol-1-ylbutan-2-amine —— C16H21N3O
    (2R,3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-pyrazol-1-ylbutan-2-amine