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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
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-[1-(3-methoxypropyl)-2,5-dimethylpyrrol-3-yl]ethanone —— C25H35N3O3
    2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-[1-(3-methoxypropyl)-2,5-dimethylpyrrol-3-yl]ethanone
    —— methyl 5-[2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]acetyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate —— C23H31N3O4+2
    methyl 5-[2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]acetyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate
    —— 3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-phenyl-1,2-oxazole —— C23H25N3O2
    3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-phenyl-1,2-oxazole
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-(1-ethyl-2,5-dimethylpyrrol-3-yl)ethanone —— C23H33N3O2+2
    2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-(1-ethyl-2,5-dimethylpyrrol-3-yl)ethanone
    —— 2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]benzonitrile —— C21H25N3O+2
    2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]benzonitrile
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-(2,5-dimethyl-1-prop-2-enylpyrrol-3-yl)ethanone —— C24H33N3O2+2
    2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-(2,5-dimethyl-1-prop-2-enylpyrrol-3-yl)ethanone
    —— (2R)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]propanenitrile —— C16H21N3O
    (2R)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]propanenitrile
    —— 2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole —— C17H22N4O2
    2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-methyl-1,3,4-oxadiazole
    —— 2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-phenyl-1,3,4-oxadiazole —— C22H24N4O2
    2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-phenyl-1,3,4-oxadiazole
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-(1,2,5-trimethylpyrrol-3-yl)ethanone —— C22H31N3O2+2
    2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-(1,2,5-trimethylpyrrol-3-yl)ethanone
    —— 2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-[2,5-dimethyl-1-(1H-1,2,4-triazol-5-yl)pyrrol-3-yl]ethanone —— C23H28N6O2
    2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-[2,5-dimethyl-1-(1H-1,2,4-triazol-5-yl)pyrrol-3-yl]ethanone
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-[1-(3-methoxypropyl)-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-(3-methoxypropyl)-2,5-dimethylpyrrol-3-yl]ethanone
    —— (2S)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]propanenitrile —— C16H23N3O+2
    (2S)-2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]propanenitrile
    —— 1-(2,3-dihydro-1-benzofuran-5-yl)-2-[3-[(R)-methylsulfinyl]-1,2,4-triazol-4-yl]ethanone —— C13H13N3O3S
    1-(2,3-dihydro-1-benzofuran-5-yl)-2-[3-[(R)-methylsulfinyl]-1,2,4-triazol-4-yl]ethanone
    —— 1-(2,3-dihydro-1-benzofuran-5-yl)-2-[3-[(S)-methylsulfinyl]-1,2,4-triazol-4-yl]ethanone —— C13H13N3O3S
    1-(2,3-dihydro-1-benzofuran-5-yl)-2-[3-[(S)-methylsulfinyl]-1,2,4-triazol-4-yl]ethanone
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S,3S)-2-phenyloxolan-3-yl]urea —— C19H20N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S,3S)-2-phenyloxolan-3-yl]urea
    —— 3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylmethyl)urea —— C18H21N3O2S
    3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylmethyl)urea
    —— 3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylmethyl)urea —— C18H21N3O2S
    3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylmethyl)urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R,3R)-2-phenyloxolan-3-yl]urea —— C19H20N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R,3R)-2-phenyloxolan-3-yl]urea
    —— 3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea —— C16H19N3O2S
    3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R,3S)-2-phenyloxolan-3-yl]urea —— C19H20N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R,3S)-2-phenyloxolan-3-yl]urea
    —— 3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea —— C16H19N3O2S
    3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea
    —— (3R)-N-(2-phenylmethoxyethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H19NO3
    (3R)-N-(2-phenylmethoxyethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2R)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H16FNO3
    (3R)-N-[(2R)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(2S)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H16FNO3
    (3S)-N-[(2S)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(2R)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H16FNO3
    (3S)-N-[(2R)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2S)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H16FNO3
    (3R)-N-[(2S)-2-(2-fluorophenyl)-2-hydroxyethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1S)-2-[(S)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H19NO3S
    (3S)-N-[(1S)-2-[(S)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1S)-2-[(R)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H19NO3S
    (3S)-N-[(1S)-2-[(R)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1R)-2-[(R)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H19NO3S
    (3S)-N-[(1R)-2-[(R)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1R)-2-[(S)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H19NO3S
    (3S)-N-[(1R)-2-[(S)-methylsulfinyl]-1-phenylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-pyridin-3-ylpropanamide —— C20H24N2O3
    (2R)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-pyridin-3-ylpropanamide
    —— (2S)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-pyridin-3-ylpropanamide —— C20H24N2O3
    (2S)-N-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethyl]-2-pyridin-3-ylpropanamide
    —— N-[2-[(2-chlorophenyl)methyl]pyrazol-3-yl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C22H22ClN3O3
    N-[2-[(2-chlorophenyl)methyl]pyrazol-3-yl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(1R,6S)-9-propan-2-yl-3,9-diazabicyclo[4.2.1]nonan-3-yl]methanone —— C19H26N2O2
    [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(1R,6S)-9-propan-2-yl-3,9-diazabicyclo[4.2.1]nonan-3-yl]methanone
    —— (2R)-6-(chloromethyl)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran —— C12H15ClO2
    (2R)-6-(chloromethyl)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran
    —— N-[(3S)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(5-methyl-1,2-oxazol-3-yl)acetamide —— C14H12Cl2N2O3
    N-[(3S)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(5-methyl-1,2-oxazol-3-yl)acetamide
    —— N-[(3R)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(5-methyl-1,2-oxazol-3-yl)acetamide —— C14H12Cl2N2O3
    N-[(3R)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(5-methyl-1,2-oxazol-3-yl)acetamide
    —— (2S)-N-(2-cyanoethyl)-7-fluoro-N-(2-methoxyethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H17FN2O3
    (2S)-N-(2-cyanoethyl)-7-fluoro-N-(2-methoxyethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(2-cyanoethyl)-7-fluoro-N-(2-methoxyethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H17FN2O3
    (2R)-N-(2-cyanoethyl)-7-fluoro-N-(2-methoxyethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— thiophen-3-ylmethyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate —— C14H12O3S
    thiophen-3-ylmethyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— thiophen-3-ylmethyl (3S)-2,3-dihydro-1-benzofuran-3-carboxylate —— C14H12O3S
    thiophen-3-ylmethyl (3S)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— [(2R)-but-3-yn-2-yl] (3S)-2,3-dihydro-1-benzofuran-3-carboxylate —— C13H12O3
    [(2R)-but-3-yn-2-yl] (3S)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— [(2R)-but-3-yn-2-yl] (3R)-2,3-dihydro-1-benzofuran-3-carboxylate —— C13H12O3
    [(2R)-but-3-yn-2-yl] (3R)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— [(2S)-but-3-yn-2-yl] (3S)-2,3-dihydro-1-benzofuran-3-carboxylate —— C13H12O3
    [(2S)-but-3-yn-2-yl] (3S)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— [(2S)-but-3-yn-2-yl] (3R)-2,3-dihydro-1-benzofuran-3-carboxylate —— C13H12O3
    [(2S)-but-3-yn-2-yl] (3R)-2,3-dihydro-1-benzofuran-3-carboxylate
    —— [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[(1R)-1-(4-methylphenyl)-2-morpholin-4-ium-4-ylethyl]azanium —— C25H36N2O3+2
    [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[(1R)-1-(4-methylphenyl)-2-morpholin-4-ium-4-ylethyl]azanium
    —— [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[(1R)-1-(4-methylphenyl)-2-morpholin-4-ium-4-ylethyl]azanium —— C25H36N2O3+2
    [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[(1R)-1-(4-methylphenyl)-2-morpholin-4-ium-4-ylethyl]azanium
    —— (1R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methylphenyl)-2-morpholin-4-ylethanamine —— C25H34N2O3
    (1R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methylphenyl)-2-morpholin-4-ylethanamine
    —— (2S)-5-chloro-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H12ClNO3
    (2S)-5-chloro-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide