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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)-6-hydroxy-3-(3-hydroxypropylamino)-2H-1-benzofuran-3-carbonitrile —— C12H14N2O3
    (3S)-6-hydroxy-3-(3-hydroxypropylamino)-2H-1-benzofuran-3-carbonitrile
    —— (R)-cycloheptyl-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine —— C17H25NO
    (R)-cycloheptyl-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine
    —— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-hydroxyethylamino)acetonitrile —— C12H14N2O2
    (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-hydroxyethylamino)acetonitrile
    —— (3R)-6-hydroxy-3-(3-hydroxypropylamino)-2H-1-benzofuran-3-carbonitrile —— C12H14N2O3
    (3R)-6-hydroxy-3-(3-hydroxypropylamino)-2H-1-benzofuran-3-carbonitrile
    —— (S)-cycloheptyl-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine —— C17H25NO
    (S)-cycloheptyl-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine
    —— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-hydroxyethylamino)acetonitrile —— C12H14N2O2
    (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-hydroxyethylamino)acetonitrile
    —— (3R)-6-hydroxy-3-(2-hydroxyethylamino)-2H-1-benzofuran-3-carbonitrile —— C11H12N2O3
    (3R)-6-hydroxy-3-(2-hydroxyethylamino)-2H-1-benzofuran-3-carbonitrile
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-ethyl-1H-1,2,4-triazol-3-yl)sulfanyl]acetamide —— C15H18N4O2S
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-ethyl-1H-1,2,4-triazol-3-yl)sulfanyl]acetamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-ethyl-1H-1,2,4-triazol-3-yl)sulfanyl]acetamide —— C15H18N4O2S
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-ethyl-1H-1,2,4-triazol-3-yl)sulfanyl]acetamide
    —— (3R,6R)-1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-N-(2-methoxyethyl)-6-methylpiperidine-3-carboxamide —— C18H26N2O5S
    (3R,6R)-1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-N-(2-methoxyethyl)-6-methylpiperidine-3-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-pyridin-2-ylethanesulfonamide —— C19H24N2O4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-pyridin-2-ylethanesulfonamide
    —— 2-(3-cyano-1,2,4-triazol-1-yl)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C14H13N5O2
    2-(3-cyano-1,2,4-triazol-1-yl)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[[5-(2-methylpropylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C17H22N4O2S2
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[[5-(2-methylpropylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
    —— 2-(3-cyano-1,2,4-triazol-1-yl)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C14H13N5O2
    2-(3-cyano-1,2,4-triazol-1-yl)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[[5-(propylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C16H20N4O2S2
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[[5-(propylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[[5-(propylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C16H20N4O2S2
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[[5-(propylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
    —— 2-[(3-cyano-4-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C21H21N3O2S
    2-[(3-cyano-4-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetamide —— C14H15N3O2S3
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetamide
    —— 2-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]thiophene-2,4-dicarboxamide —— C15H14N2O3S
    2-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]thiophene-2,4-dicarboxamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]acetamide —— C15H16N2O2S2
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]acetamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-methyl-4-prop-2-enyl-1,2,4-triazol-3-yl)sulfanyl]acetamide —— C17H20N4O2S
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-[(5-methyl-4-prop-2-enyl-1,2,4-triazol-3-yl)sulfanyl]acetamide
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]ethanone —— C18H20N2O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]ethanone
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methanone —— C17H17ClN2O3
    [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methanone —— C17H17ClN2O3
    [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methanone
    —— (2S)-N-[2-methyl-2-[(3S)-3-methylpiperidin-1-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H28N2O2
    (2S)-N-[2-methyl-2-[(3S)-3-methylpiperidin-1-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]ethanone —— C18H20N2O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]ethanone
    —— (2S,3R)-2-methyl-5-propyl-2,3-dihydro-1-benzofuran-3-amine —— C12H17NO
    (2S,3R)-2-methyl-5-propyl-2,3-dihydro-1-benzofuran-3-amine
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(4-formylphenoxy)acetamide —— C18H17NO4
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(4-formylphenoxy)acetamide
    —— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-methoxyethylamino)ethanol —— C13H19NO3
    (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-methoxyethylamino)ethanol
    —— (3S)-3-[(3S)-3-(methylamino)piperidin-1-yl]-2,3-dihydro-1-benzofuran-6-ol —— C14H20N2O2
    (3S)-3-[(3S)-3-(methylamino)piperidin-1-yl]-2,3-dihydro-1-benzofuran-6-ol
    —— (2R)-N-[(2-ethoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H19NO3
    (2R)-N-[(2-ethoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 4-bromo-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-1H-pyrazole-3-carboxamide —— C17H20BrN3O3
    4-bromo-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-1H-pyrazole-3-carboxamide
    —— 4-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-1H-pyrazole-3-carboxamide —— C17H20BrN3O3
    4-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-1H-pyrazole-3-carboxamide
    —— N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-1-phenylmethanamine —— C17H19NO
    N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-1-phenylmethanamine
    —— (2S)-N-(3-benzylsulfonylpropyl)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H20ClNO4S
    (2S)-N-(3-benzylsulfonylpropyl)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-chloro-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-6-methylpyrimidin-4-amine —— C14H14ClN3O
    2-chloro-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-6-methylpyrimidin-4-amine
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,3,5-trimethylpyrazole-4-sulfonamide —— C18H25N3O4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,3,5-trimethylpyrazole-4-sulfonamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,3,5-trimethylpyrazole-4-sulfonamide —— C18H25N3O4S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,3,5-trimethylpyrazole-4-sulfonamide
    —— (2R)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methylpropan-1-amine —— C14H21NO2
    (2R)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methylpropan-1-amine
    —— methyl 5-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamoyl]-2-methyl-4-propyl-1H-pyrrole-3-carboxylate —— C20H24N2O4
    methyl 5-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamoyl]-2-methyl-4-propyl-1H-pyrrole-3-carboxylate
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-1-[[(2R)-oxan-2-yl]methyl]urea —— C20H30N2O4
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-1-[[(2R)-oxan-2-yl]methyl]urea
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-1-[[(2R)-oxan-2-yl]methyl]urea —— C20H30N2O4
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-1-[[(2R)-oxan-2-yl]methyl]urea
    —— 1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(3S)-1-ethylpiperidin-3-yl]urea —— C20H31N3O3
    1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(3S)-1-ethylpiperidin-3-yl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-sulfanylidenepyrimidin-4-one —— C13H12N2O2S
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-sulfanylidenepyrimidin-4-one
    —— (2S)-2-[(3S)-3,6-dihydroxy-2H-1-benzofuran-3-yl]propanoic acid —— C11H12O5
    (2S)-2-[(3S)-3,6-dihydroxy-2H-1-benzofuran-3-yl]propanoic acid
    —— (2S,3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-hydroxy-2-methylpropanoic acid —— C12H14O4
    (2S,3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-hydroxy-2-methylpropanoic acid
    —— (2R)-2-[(3R)-3,6-dihydroxy-2H-1-benzofuran-3-yl]butanoic acid —— C12H14O5
    (2R)-2-[(3R)-3,6-dihydroxy-2H-1-benzofuran-3-yl]butanoic acid
    —— (2R)-2-[(3R)-3,6-dihydroxy-2H-1-benzofuran-3-yl]propanoic acid —— C11H12O5
    (2R)-2-[(3R)-3,6-dihydroxy-2H-1-benzofuran-3-yl]propanoic acid
    —— ethyl (3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-hydroxy-2,2-dimethylpropanoate —— C15H20O4
    ethyl (3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-hydroxy-2,2-dimethylpropanoate
    —— methyl (2R)-2-[(3S)-3,6-dihydroxy-2H-1-benzofuran-3-yl]butanoate —— C13H16O5
    methyl (2R)-2-[(3S)-3,6-dihydroxy-2H-1-benzofuran-3-yl]butanoate