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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
    —— (3S)-N-[(2S)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H24N2O2S
    (3S)-N-[(2S)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(2R)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H24N2O2
    (3S)-N-[(2R)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(2S)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H23ClN2O2
    (3S)-N-[(2S)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2R)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H23ClN2O2
    (3R)-N-[(2R)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[3-(4-ethylpiperazin-1-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H27N3O2
    (3R)-N-[3-(4-ethylpiperazin-1-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethyl]-5-thiophen-2-yl-1,3,4-oxadiazole —— C21H24N4O2S
    2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethyl]-5-thiophen-2-yl-1,3,4-oxadiazole
    —— 3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-(4-fluorophenyl)-4-methyl-1,2-oxazole —— C24H26FN3O2
    3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-(4-fluorophenyl)-4-methyl-1,2-oxazole
    —— 2-[(1R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethyl]-5-(4-methoxyphenyl)-1,3,4-oxadiazole —— C24H28N4O3
    2-[(1R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethyl]-5-(4-methoxyphenyl)-1,3,4-oxadiazole
    —— 2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethyl]-5-(4-methoxyphenyl)-1,3,4-oxadiazole —— C24H30N4O3+2
    2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethyl]-5-(4-methoxyphenyl)-1,3,4-oxadiazole
    —— 7-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-2-ethyl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one —— C21H25N5O2S
    7-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-2-ethyl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
    —— 2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-[1-[(2S)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]ethanone —— C25H37N3O3+2
    2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-[1-[(2S)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]ethanone
    —— 2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethyl]-5-(3-methylphenyl)-1,3,4-oxadiazole —— C24H30N4O2+2
    2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethyl]-5-(3-methylphenyl)-1,3,4-oxadiazole
    —— 2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-7-methyl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one —— C20H23N5O2S
    2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-7-methyl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
    —— (2R)-1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]propan-1-one —— C24H33N3O3+2
    (2R)-1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]propan-1-one
    —— 2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazole —— C22H26N4O3
    2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazole
    —— 3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-phenyl-1,2-oxazole —— C23H27N3O2+2
    3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-phenyl-1,2-oxazole
    —— 2-[(1R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethyl]-5-(3-methylphenyl)-1,3,4-oxadiazole —— C24H28N4O2
    2-[(1R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethyl]-5-(3-methylphenyl)-1,3,4-oxadiazole
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-(1-ethyl-2,5-dimethylpyrrol-3-yl)ethanone —— C23H31N3O2
    2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-(1-ethyl-2,5-dimethylpyrrol-3-yl)ethanone
    —— methyl 5-[2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]acetyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate —— C23H29N3O4
    methyl 5-[2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]acetyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate
    —— (2S)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]propanenitrile —— C16H21N3O
    (2S)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]propanenitrile
    —— 3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]benzonitrile —— C21H23N3O
    3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]benzonitrile
    —— (4-methyl-2-phenyl-1,3-thiazol-5-yl)methyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate —— C20H17NO3S
    (4-methyl-2-phenyl-1,3-thiazol-5-yl)methyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— (3S)-N-[3-(cyclohexylmethoxy)pyridin-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H24N2O3
    (3S)-N-[3-(cyclohexylmethoxy)pyridin-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[2-(2-phenylethyl)pyrazol-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H19N3O2
    (3R)-N-[2-(2-phenylethyl)pyrazol-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[2-(3-chlorophenyl)-2-methylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H20ClNO2
    (3S)-N-[2-(3-chlorophenyl)-2-methylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-(2,2-difluoroethyl)-N-propyl-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H17F2NO2
    (3R)-N-(2,2-difluoroethyl)-N-propyl-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-(furan-2-yl)-1,3,4-oxadiazole —— C20H24N4O3+2
    2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-(furan-2-yl)-1,3,4-oxadiazole
    —— (3S)-N-[2-(2-fluorophenyl)-2-methylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H20FNO2
    (3S)-N-[2-(2-fluorophenyl)-2-methylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2-cyclohexyloxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H24N2O3
    (3R)-N-[(2-cyclohexyloxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[2-(2-phenylethyl)pyrazol-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H19N3O2
    (3S)-N-[2-(2-phenylethyl)pyrazol-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethanone —— C23H31N3O3+2
    1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethanone
    —— (3R)-N-[3-(thiophene-2-carbonylamino)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H18N2O3S
    (3R)-N-[3-(thiophene-2-carbonylamino)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-[1-(2-methoxyethyl)-2,5-dimethylpyrrol-3-yl]ethanone —— C24H35N3O3+2
    2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-[1-(2-methoxyethyl)-2,5-dimethylpyrrol-3-yl]ethanone
    —— (3S)-N-methyl-N-[3-(3-phenyl-1,2-oxazol-5-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C22H22N2O3
    (3S)-N-methyl-N-[3-(3-phenyl-1,2-oxazol-5-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(2-cyclohexyloxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H24N2O3
    (3S)-N-[(2-cyclohexyloxypyridin-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[2-methyl-2-(3-methylphenyl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H23NO2
    (3S)-N-[2-methyl-2-(3-methylphenyl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[2-(3-methylphenyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H19NO2
    (3S)-N-[2-(3-methylphenyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[[1-(2,6-difluorophenyl)cyclopentyl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H21F2NO2
    (3R)-N-[[1-(2,6-difluorophenyl)cyclopentyl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-methyl-N-[3-(3-phenyl-1,2-oxazol-5-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C22H22N2O3
    (3R)-N-methyl-N-[3-(3-phenyl-1,2-oxazol-5-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 4-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]benzonitrile —— C21H25N3O+2
    4-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]benzonitrile
    —— (5-phenyl-1,3,4-oxadiazol-2-yl)methyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate —— C18H14N2O4
    (5-phenyl-1,3,4-oxadiazol-2-yl)methyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— (3R)-N-[[6-(cyclopropylmethoxy)pyridin-3-yl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H20N2O3
    (3R)-N-[[6-(cyclopropylmethoxy)pyridin-3-yl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(4R)-4-methylazepan-1-yl]methanone —— C16H21NO2
    [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(4R)-4-methylazepan-1-yl]methanone
    —— (3R)-N-[1-(2-pyridin-4-ylethyl)pyrazol-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H18N4O2
    (3R)-N-[1-(2-pyridin-4-ylethyl)pyrazol-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[1-[2-(cyclopentylamino)-2-oxoethyl]pyrazol-4-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H22N4O3
    (3S)-N-[1-[2-(cyclopentylamino)-2-oxoethyl]pyrazol-4-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[2-methyl-2-(3-methylphenyl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H23NO2
    (3R)-N-[2-methyl-2-(3-methylphenyl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[[1-(2-methylphenyl)cyclopropyl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H21NO2
    (3R)-N-[[1-(2-methylphenyl)cyclopropyl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(3-chloro-4-fluorophenyl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H13ClFNO2
    (3S)-N-[(3-chloro-4-fluorophenyl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[[1-(2-methylphenyl)cyclopropyl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H21NO2
    (3S)-N-[[1-(2-methylphenyl)cyclopropyl]methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1R)-1-(3-ethoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H21NO3
    (3S)-N-[(1R)-1-(3-ethoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide