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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
    —— tert-butyl N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]carbamate —— C17H24N2O4
    tert-butyl N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]carbamate
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C14H18N2O3
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— (2S)-N-[2-(cyclopropylmethoxy)ethyl]-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H18FNO3
    (2S)-N-[2-(cyclopropylmethoxy)ethyl]-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(4-cyano-1-methylpiperidin-4-yl)-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18FN3O2
    (2R)-N-(4-cyano-1-methylpiperidin-4-yl)-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3S)-N-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H11F3N2O2S
    (3S)-N-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H11F3N2O2S
    (3R)-N-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C14H18N2O3
    N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— (2S)-N-(4-cyano-1-methylpiperidin-4-yl)-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18FN3O2
    (2S)-N-(4-cyano-1-methylpiperidin-4-yl)-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-fluoro-N-[2-(1-propan-2-ylpyrazol-3-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H20FN3O2
    (2R)-5-fluoro-N-[2-(1-propan-2-ylpyrazol-3-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-fluoro-N-[(3S)-1-pyrimidin-2-ylpiperidin-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H19FN4O2
    (2S)-5-fluoro-N-[(3S)-1-pyrimidin-2-ylpiperidin-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-fluoro-N-[(2-methoxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H15FN2O3
    (2S)-5-fluoro-N-[(2-methoxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (4-benzylpiperazin-4-ium-1-yl)-[(2R)-2,3-dihydro-1-benzofuran-2-yl]methanone —— C20H23N2O2+
    (4-benzylpiperazin-4-ium-1-yl)-[(2R)-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-thiophen-3-ylpyrrolidin-1-yl]methanone —— C17H16FNO2S
    [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-thiophen-3-ylpyrrolidin-1-yl]methanone
    —— (2R)-5-fluoro-N-[(2-methoxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H15FN2O3
    (2R)-5-fluoro-N-[(2-methoxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-benzyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H15NO2
    (2R)-N-benzyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-fluoro-N-[2-(1-propan-2-ylpyrazol-3-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H20FN3O2
    (2S)-5-fluoro-N-[2-(1-propan-2-ylpyrazol-3-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-thiophen-3-ylpyrrolidin-1-yl]methanone —— C17H16FNO2S
    [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-thiophen-3-ylpyrrolidin-1-yl]methanone
    —— (2R)-N-[2-(cyclohexanecarbonylamino)ethyl]-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H23FN2O3
    (2R)-N-[2-(cyclohexanecarbonylamino)ethyl]-5-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-thiophen-3-ylpyrrolidin-1-yl]methanone —— C17H16FNO2S
    [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-thiophen-3-ylpyrrolidin-1-yl]methanone
    —— 3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1R)-1-pyridin-4-ylpropyl]urea —— C20H25N3O2
    3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1R)-1-pyridin-4-ylpropyl]urea
    —— 3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1S)-1-pyridin-4-ylpropyl]urea —— C20H25N3O2
    3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1S)-1-pyridin-4-ylpropyl]urea
    —— 3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1S)-1-pyridin-4-ylpropyl]urea —— C20H25N3O2
    3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1S)-1-pyridin-4-ylpropyl]urea
    —— 3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1R)-1-pyridin-4-ylpropyl]urea —— C20H25N3O2
    3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(1R)-1-pyridin-4-ylpropyl]urea
    —— (2S)-N-[3-[(3-methylfuran-2-carbonyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H20N2O4
    (2S)-N-[3-[(3-methylfuran-2-carbonyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[3-[(3-methylfuran-2-carbonyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H20N2O4
    (2R)-N-[3-[(3-methylfuran-2-carbonyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-methylsulfanylbutan-2-yl]urea —— C14H20N2O2S
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-methylsulfanylbutan-2-yl]urea
    —— 1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(3R)-4,4,4-trifluoro-3-hydroxybutyl]urea —— C15H19F3N2O3
    1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(3R)-4,4,4-trifluoro-3-hydroxybutyl]urea
    —— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(3S)-4,4,4-trifluoro-3-hydroxybutyl]urea —— C15H19F3N2O3
    1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(3S)-4,4,4-trifluoro-3-hydroxybutyl]urea
    —— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(3R)-4,4,4-trifluoro-3-hydroxybutyl]urea —— C15H19F3N2O3
    1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(3R)-4,4,4-trifluoro-3-hydroxybutyl]urea
    —— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-methylsulfanylbutan-2-yl]urea —— C14H20N2O2S
    1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-methylsulfanylbutan-2-yl]urea
    —— (2R)-7-chloro-2-methyl-N-(1,3-thiazol-4-ylmethyl)-2,3-dihydro-1-benzofuran-5-sulfonamide —— C13H13ClN2O3S2
    (2R)-7-chloro-2-methyl-N-(1,3-thiazol-4-ylmethyl)-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-methylsulfanylbutan-2-yl]urea —— C14H20N2O2S
    1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-methylsulfanylbutan-2-yl]urea
    —— (2S)-7-chloro-2-methyl-N-(1,3-thiazol-4-ylmethyl)-2,3-dihydro-1-benzofuran-5-sulfonamide —— C13H13ClN2O3S2
    (2S)-7-chloro-2-methyl-N-(1,3-thiazol-4-ylmethyl)-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-methylsulfanylbutan-2-yl]urea —— C14H20N2O2S
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-methylsulfanylbutan-2-yl]urea
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4-methylaniline —— C19H22N2O2
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4-methylaniline
    —— 3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(4-methyl-1,3-thiazol-2-yl)methyl]urea —— C17H21N3O2S
    3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(4-methyl-1,3-thiazol-2-yl)methyl]urea
    —— 3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(4-methyl-1,3-thiazol-2-yl)methyl]urea —— C17H21N3O2S
    3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-[(4-methyl-1,3-thiazol-2-yl)methyl]urea
    —— (2S,3R)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H18N4O2
    (2S,3R)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R,3S)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H18N4O2
    (2R,3S)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R,3R)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H18N4O2
    (2R,3R)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S,3S)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H18N4O2
    (2S,3S)-3-methyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[2-[(R)-tert-butylsulfinyl]ethyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea —— C15H22N2O3S
    1-[2-[(R)-tert-butylsulfinyl]ethyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(S)-methylsulfinyl]ethyl]urea —— C14H20N2O3S
    1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(S)-methylsulfinyl]ethyl]urea
    —— 1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(R)-methylsulfinyl]ethyl]urea —— C14H20N2O3S
    1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(R)-methylsulfinyl]ethyl]urea
    —— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(S)-methylsulfinyl]ethyl]urea —— C14H20N2O3S
    1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(S)-methylsulfinyl]ethyl]urea
    —— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(R)-methylsulfinyl]ethyl]urea —— C14H20N2O3S
    1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[2-[(R)-methylsulfinyl]ethyl]urea
    —— 1-[2-[(S)-tert-butylsulfinyl]ethyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea —— C15H22N2O3S
    1-[2-[(S)-tert-butylsulfinyl]ethyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[2-[(S)-tert-butylsulfinyl]ethyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea —— C15H22N2O3S
    1-[2-[(S)-tert-butylsulfinyl]ethyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[2-[(R)-tert-butylsulfinyl]ethyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea —— C15H22N2O3S
    1-[2-[(R)-tert-butylsulfinyl]ethyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— (2S)-N-[1-(6-methylpyridin-2-yl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H23N3O2
    (2S)-N-[1-(6-methylpyridin-2-yl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide