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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
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methylpyrrole-2-carboxamide —— C18H22N2O3
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methylpyrrole-2-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methylpyrrole-2-carboxamide —— C18H22N2O3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methylpyrrole-2-carboxamide
    —— (2R)-5-chloro-N-methyl-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H18ClNO2
    (2R)-5-chloro-N-methyl-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-methyl-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H18ClNO2
    (2R)-5-chloro-N-methyl-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[[4-(dimethylamino)phenyl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H21ClN2O2
    (2S)-5-chloro-N-[[4-(dimethylamino)phenyl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methanone —— C17H21ClN2O4S
    [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methanone
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3S)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methanone —— C17H21ClN2O4S
    [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3S)-1,1-dioxothiolan-3-yl]piperazin-1-yl]methanone
    —— [(2S)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-4-ium-1-yl]methanone —— C17H22ClN2O4S+
    [(2S)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-4-ium-1-yl]methanone
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-4-ium-1-yl]methanone —— C17H22ClN2O4S+
    [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3R)-1,1-dioxothiolan-3-yl]piperazin-4-ium-1-yl]methanone
    —— (Z)-1-(2,3-dihydro-1-benzofuran-5-yl)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)prop-2-en-1-one —— C18H16N2O2S
    (Z)-1-(2,3-dihydro-1-benzofuran-5-yl)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)prop-2-en-1-one
    —— (Z)-1-(2,3-dihydro-1-benzofuran-5-yl)-3-thiophen-3-ylprop-2-en-1-one —— C15H12O2S
    (Z)-1-(2,3-dihydro-1-benzofuran-5-yl)-3-thiophen-3-ylprop-2-en-1-one
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[4-[(Z)-2-phenylethenyl]sulfonylpiperazin-1-yl]ethanone —— C22H24N2O4S
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[4-[(Z)-2-phenylethenyl]sulfonylpiperazin-1-yl]ethanone
    —— (Z)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-3-thiophen-3-ylprop-2-enamide —— C18H14N2O2S2
    (Z)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-3-thiophen-3-ylprop-2-enamide
    —— (Z)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-3-(furan-2-yl)prop-2-enamide —— C18H14N2O3S
    (Z)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-3-(furan-2-yl)prop-2-enamide
    —— 5-[(Z)-3-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-oxoprop-1-enyl]-1,3-dimethylpyrimidine-2,4-dione —— C22H26N4O4
    5-[(Z)-3-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-oxoprop-1-enyl]-1,3-dimethylpyrimidine-2,4-dione
    —— (2S,3S)-2,3-dimethyl-N-[[2-(pyrrolidin-1-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C23H28N2O2
    (2S,3S)-2,3-dimethyl-N-[[2-(pyrrolidin-1-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (5E)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C22H28N2O4S2
    (5E)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (5E)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C22H28N2O4S2
    (5E)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (2S,3S)-2,3-dimethyl-N-[[2-(pyrrolidin-1-ium-1-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C23H29N2O2+
    (2S,3S)-2,3-dimethyl-N-[[2-(pyrrolidin-1-ium-1-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]prop-2-enamide —— C21H23N3O3S
    (Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]prop-2-enamide
    —— (Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]prop-2-enamide —— C21H23N3O3S
    (Z)-3-(2,6-dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]prop-2-enamide
    —— (2E,4Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]hexa-2,4-dienamide —— C17H21NO3
    (2E,4Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]hexa-2,4-dienamide
    —— (2Z,4Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]hexa-2,4-dienamide —— C17H21NO3
    (2Z,4Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]hexa-2,4-dienamide
    —— (2Z,4E)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]hexa-2,4-dienamide —— C17H21NO3
    (2Z,4E)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]hexa-2,4-dienamide
    —— (Z)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylfuran-2-yl)prop-2-enamide —— C19H21NO4
    (Z)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylfuran-2-yl)prop-2-enamide
    —— (Z)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylthiophen-2-yl)prop-2-enamide —— C19H21NO3S
    (Z)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylthiophen-2-yl)prop-2-enamide
    —— (Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]prop-2-enamide —— C23H21FN2O3S
    (Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]prop-2-enamide
    —— (Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylthiophen-2-yl)prop-2-enamide —— C19H21NO3S
    (Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylthiophen-2-yl)prop-2-enamide
    —— (Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylfuran-2-yl)prop-2-enamide —— C19H21NO4
    (Z)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(5-methylfuran-2-yl)prop-2-enamide
    —— (Z)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]prop-2-enamide —— C23H21FN2O3S
    (Z)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]prop-2-enamide
    —— [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-2-phenylethenyl]sulfonylpiperazin-1-yl]methanone —— C23H26N2O4S
    [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-2-phenylethenyl]sulfonylpiperazin-1-yl]methanone
    —— [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methanone —— C24H28N2O2
    [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methanone
    —— [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-2-phenylethenyl]sulfonylpiperazin-1-yl]methanone —— C23H26N2O4S
    [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-2-phenylethenyl]sulfonylpiperazin-1-yl]methanone
    —— [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methanone —— C24H28N2O2
    [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methanone
    —— 3-[(Z)-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile —— C19H19N3O3
    3-[(Z)-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile
    —— 3-[(Z)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile —— C19H19N3O3
    3-[(Z)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile
    —— N-[[4-(difluoromethoxy)-3-methoxyphenyl]methyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C21H23F2NO5
    N-[[4-(difluoromethoxy)-3-methoxyphenyl]methyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-(2-fluorophenyl)ethyl]acetamide —— C20H22FNO3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-(2-fluorophenyl)ethyl]acetamide
    —— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(3,4,5-trimethoxybenzyl)acetamide —— C22H27NO6
    2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(3,4,5-trimethoxybenzyl)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)ethanone —— C23H25NO3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)ethanone
    —— [2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl] N,N-diethylcarbamodithioate —— C19H28N2O3S2
    [2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl] N,N-diethylcarbamodithioate
    —— [2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl] N,N-diethylcarbamodithioate —— C19H28N2O3S2
    [2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl] N,N-diethylcarbamodithioate
    —— (2R)-N-(2-benzylsulfanylethyl)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H18ClNO2S
    (2R)-N-(2-benzylsulfanylethyl)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[2-[(2-fluorophenyl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H17ClFNO2S
    (2R)-5-chloro-N-[2-[(2-fluorophenyl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[2-[(2-fluorophenyl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H17ClFNO2S
    (2S)-5-chloro-N-[2-[(2-fluorophenyl)methylsulfanyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[2-(3-methylphenoxy)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H18ClNO3
    (2S)-5-chloro-N-[2-(3-methylphenoxy)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[(2-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16ClNO2
    (2R)-5-chloro-N-[(2-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[2-(3-methylphenoxy)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H18ClNO3
    (2R)-5-chloro-N-[2-(3-methylphenoxy)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3R)-3-(4-chloro-2,3-dihydro-1-benzofuran-5-yl)-3-hydroxypropanoic acid —— C11H11ClO4
    (3R)-3-(4-chloro-2,3-dihydro-1-benzofuran-5-yl)-3-hydroxypropanoic acid
    —— (1R,2S)-2-amino-1-(4-chloro-2,3-dihydro-1-benzofuran-5-yl)butan-1-ol —— C12H16ClNO2
    (1R,2S)-2-amino-1-(4-chloro-2,3-dihydro-1-benzofuran-5-yl)butan-1-ol