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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,N-dibutyl-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C20H31NO3
    N,N-dibutyl-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N,N-diethylacetamide —— C16H23NO3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N,N-diethylacetamide
    —— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N,N-bis(2-methoxyethyl)acetamide —— C18H27NO5
    2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N,N-bis(2-methoxyethyl)acetamide
    —— (2S)-N-[[1-[(3R)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H25N3O4S
    (2S)-N-[[1-[(3R)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[[1-[(3R)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H25N3O4S
    (2R)-N-[[1-[(3R)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[[1-[(3S)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H25N3O4S
    (2R)-N-[[1-[(3S)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-fluoro-2-methoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C21H24FN2O3+
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-fluoro-2-methoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-fluoro-2-methoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone —— C21H24FN2O3+
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-fluoro-2-methoxyphenyl)methyl]piperazin-4-ium-1-yl]methanone
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-fluoro-2-methoxyphenyl)methyl]piperazin-1-yl]methanone —— C21H23FN2O3
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-fluoro-2-methoxyphenyl)methyl]piperazin-1-yl]methanone
    —— (2R)-N-[(3,4,5-trimethoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H21NO5
    (2R)-N-[(3,4,5-trimethoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(2-phenylsulfanylethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H17NO2S
    (2R)-N-(2-phenylsulfanylethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2,5-dimethylfuran-3-carboxamide —— C19H22N2O4
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2,5-dimethylfuran-3-carboxamide
    —— N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2,5-dimethylfuran-3-carboxamide —— C19H22N2O4
    N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2,5-dimethylfuran-3-carboxamide
    —— 1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-2-(furan-2-yl)-2-hydroxyethyl]urea —— C18H22N2O5
    1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-2-(furan-2-yl)-2-hydroxyethyl]urea
    —— 1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-2-(furan-2-yl)-2-hydroxyethyl]urea —— C18H22N2O5
    1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-2-(furan-2-yl)-2-hydroxyethyl]urea
    —— 1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2S)-2-(furan-2-yl)-2-hydroxyethyl]urea —— C18H22N2O5
    1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2S)-2-(furan-2-yl)-2-hydroxyethyl]urea
    —— 1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2S)-2-(furan-2-yl)-2-hydroxyethyl]urea —— C18H22N2O5
    1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2S)-2-(furan-2-yl)-2-hydroxyethyl]urea
    —— 3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-[(4-methoxyphenyl)methyl]-1-methylurea —— C21H26N2O4
    3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-[(4-methoxyphenyl)methyl]-1-methylurea
    —— (3R)-N-[(1R,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H21N3O2
    (3R)-N-[(1R,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1R,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H21N3O2
    (3S)-N-[(1R,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(1S,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H21N3O2
    (3R)-N-[(1S,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1S,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H21N3O2
    (3S)-N-[(1S,2S)-2-pyrazol-1-ylcyclohexyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]urea —— C18H23N3O4
    3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]urea
    —— 1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylurea —— C19H25N3O4
    1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylurea
    —— 3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]urea —— C18H23N3O4
    3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]urea
    —— 1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylurea —— C19H25N3O4
    1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methylurea
    —— (2S)-5,6-dimethyl-N-pyridazin-3-yl-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H15N3O2
    (2S)-5,6-dimethyl-N-pyridazin-3-yl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5,6-dimethyl-N-pyridazin-3-yl-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H15N3O2
    (2R)-5,6-dimethyl-N-pyridazin-3-yl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-methylsulfanylethyl (2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C13H16O3S
    2-methylsulfanylethyl (2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— 2-methylsulfanylethyl (2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C13H16O3S
    2-methylsulfanylethyl (2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— 2-methylsulfanylethyl (2S,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C13H16O3S
    2-methylsulfanylethyl (2S,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— 1-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea —— C16H17N3O2S
    1-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea —— C18H23N3O2
    1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea
    —— (2S)-N-[(2R)-2-hydroxy-2-thiophen-3-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17NO3S
    (2S)-N-[(2R)-2-hydroxy-2-thiophen-3-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea —— C16H17N3O2S
    1-[(S)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea —— C18H23N3O2
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea
    —— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea —— C19H26N4O2
    1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea
    —— (2R)-N-[(2R)-2-(2,6-difluorophenyl)-2-hydroxyethyl]-7-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H14F3NO3
    (2R)-N-[(2R)-2-(2,6-difluorophenyl)-2-hydroxyethyl]-7-fluoro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea —— C18H23N3O2
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea
    —— 1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea —— C19H26N4O2
    1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea
    —— 1-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea —— C16H17N3O2S
    1-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea —— C18H23N3O2
    1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-4-(1-methylpyrrol-2-yl)butan-2-yl]urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(4S)-4-hydroxy-2,2-dimethylpentyl]urea —— C16H24N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(4S)-4-hydroxy-2,2-dimethylpentyl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(2R)-1-(1,3,5-trimethylpyrazol-4-yl)propan-2-yl]urea —— C19H26N4O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(2R)-1-(1,3,5-trimethylpyrazol-4-yl)propan-2-yl]urea
    —— 1-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea —— C16H17N3O2S
    1-[(R)-cyclopropyl(1,3-thiazol-2-yl)methyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— (2S)-N-[(2S)-2-hydroxy-2-thiophen-3-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17NO3S
    (2S)-N-[(2S)-2-hydroxy-2-thiophen-3-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(2S)-1-(1,3,5-trimethylpyrazol-4-yl)propan-2-yl]urea —— C19H26N4O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(2S)-1-(1,3,5-trimethylpyrazol-4-yl)propan-2-yl]urea
    —— 1-[(2R)-2-(5-chlorothiophen-2-yl)-2-hydroxyethyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea —— C15H15ClN2O3S
    1-[(2R)-2-(5-chlorothiophen-2-yl)-2-hydroxyethyl]-3-[(3S)-2,3-dihydro-1-benzofuran-3-yl]urea
    —— (2R)-N-[(2S)-2-hydroxy-2-thiophen-3-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17NO3S
    (2R)-N-[(2S)-2-hydroxy-2-thiophen-3-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(4R)-4-hydroxy-2,2-dimethylpentyl]urea —— C16H24N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(4R)-4-hydroxy-2,2-dimethylpentyl]urea