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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
    —— 5-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate —— C20H22NO5S2-
    5-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate
    —— 5-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C20H23NO5S2
    5-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
    —— 5-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C20H23NO5S2
    5-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
    —— 5-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate —— C20H22NO5S2-
    5-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoate
    —— (2S)-N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]oxolane-2-carboxamide —— C26H33N3O3
    (2S)-N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]oxolane-2-carboxamide
    —— N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]cyclobutanecarboxamide —— C26H33N3O2
    N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]cyclobutanecarboxamide
    —— (2S)-N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]oxolane-2-carboxamide —— C26H33N3O3
    (2S)-N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]oxolane-2-carboxamide
    —— 3-methoxy-N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide —— C25H33N3O3
    3-methoxy-N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide
    —— N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]cyclobutanecarboxamide —— C26H33N3O2
    N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]cyclobutanecarboxamide
    —— 2-[(3S,8aR)-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-3-yl]ethanol —— C21H32N2O3
    2-[(3S,8aR)-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-3-yl]ethanol
    —— (2R,3R)-2,3-dimethyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C17H18N2O2
    (2R,3R)-2,3-dimethyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-2,3-dimethyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C17H18N2O2
    (2R,3S)-2,3-dimethyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-2,3-dimethyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C17H18N2O2
    (2S,3R)-2,3-dimethyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— 1-(4-cyano-1-methylpyrazol-3-yl)-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]urea —— C15H15N5O2
    1-(4-cyano-1-methylpyrazol-3-yl)-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]urea
    —— 1-(4-cyano-1-methylpyrazol-3-yl)-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]urea —— C15H15N5O2
    1-(4-cyano-1-methylpyrazol-3-yl)-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]urea
    —— (3R)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-(1H-1,2,4-triazol-5-yl)piperidine-1-carboxamide —— C16H19N5O2
    (3R)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-(1H-1,2,4-triazol-5-yl)piperidine-1-carboxamide
    —— 3-[cyclopropylmethyl-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]amino]propanenitrile —— C19H26N2O2
    3-[cyclopropylmethyl-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]amino]propanenitrile
    —— 3-[cyclopropylmethyl-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]amino]propanenitrile —— C19H26N2O2
    3-[cyclopropylmethyl-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]amino]propanenitrile
    —— (2R)-7-chloro-N,2-dimethyl-N-(1-oxothian-4-yl)-2,3-dihydro-1-benzofuran-5-sulfonamide —— C15H20ClNO4S2
    (2R)-7-chloro-N,2-dimethyl-N-(1-oxothian-4-yl)-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (2S)-7-chloro-N,2-dimethyl-N-(1-oxothian-4-yl)-2,3-dihydro-1-benzofuran-5-sulfonamide —— C15H20ClNO4S2
    (2S)-7-chloro-N,2-dimethyl-N-(1-oxothian-4-yl)-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (3S)-N-(4,5-dicyano-1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H9N5O2
    (3S)-N-(4,5-dicyano-1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-(4,5-dicyano-1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H9N5O2
    (3R)-N-(4,5-dicyano-1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (2S)-N-(4,5-dicyano-1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H9N5O2
    (2S)-N-(4,5-dicyano-1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3S)-N-(5-ethyl-1H-pyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H15N3O2
    (3S)-N-(5-ethyl-1H-pyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-(5-ethyl-1H-pyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H15N3O2
    (3R)-N-(5-ethyl-1H-pyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (2S)-N-[5-(furan-3-yl)-1H-1,2,4-triazol-3-yl]-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16N4O3
    (2S)-N-[5-(furan-3-yl)-1H-1,2,4-triazol-3-yl]-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(3S)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(tetrazol-1-yl)acetamide —— C11H9Cl2N5O2
    N-[(3S)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(tetrazol-1-yl)acetamide
    —— (2R)-5,6-dimethyl-N-[2-[(6-methylpyridazin-3-yl)amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H22N4O2
    (2R)-5,6-dimethyl-N-[2-[(6-methylpyridazin-3-yl)amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[5-(furan-3-yl)-1H-1,2,4-triazol-3-yl]-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16N4O3
    (2R)-N-[5-(furan-3-yl)-1H-1,2,4-triazol-3-yl]-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5,6-dimethyl-N-[2-[(6-methylpyridazin-3-yl)amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H22N4O2
    (2S)-5,6-dimethyl-N-[2-[(6-methylpyridazin-3-yl)amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5,6-dimethyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H20N4O2
    (2R)-5,6-dimethyl-N-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(3R)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(tetrazol-1-yl)acetamide —— C11H9Cl2N5O2
    N-[(3R)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-2-(tetrazol-1-yl)acetamide
    —— [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(3S,4R)-3-methyl-4-morpholin-4-ylpyrrolidin-1-yl]methanone —— C18H23FN2O3
    [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(3S,4R)-3-methyl-4-morpholin-4-ylpyrrolidin-1-yl]methanone
    —— [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(3S,4S)-3-methyl-4-morpholin-4-ylpyrrolidin-1-yl]methanone —— C18H23FN2O3
    [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(3S,4S)-3-methyl-4-morpholin-4-ylpyrrolidin-1-yl]methanone
    —— 1-[[(2S)-1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)pyrrolidin-2-yl]methyl]-2-methylimidazole —— C17H21N3O3S
    1-[[(2S)-1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)pyrrolidin-2-yl]methyl]-2-methylimidazole
    —— [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(3R,4S)-3-methyl-4-morpholin-4-ylpyrrolidin-1-yl]methanone —— C18H23FN2O3
    [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(3R,4S)-3-methyl-4-morpholin-4-ylpyrrolidin-1-yl]methanone
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1H-1,2,4-triazol-3-yl)morpholin-4-yl]methanone —— C16H17ClN4O3
    [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1H-1,2,4-triazol-3-yl)morpholin-4-yl]methanone
    —— [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C19H23N3O3
    [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C19H23N3O3
    [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C19H23N3O3
    [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(5-methyl-1H-1,2,4-triazol-3-yl)morpholin-4-yl]ethanone —— C17H20N4O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(5-methyl-1H-1,2,4-triazol-3-yl)morpholin-4-yl]ethanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(5-methyl-1H-1,2,4-triazol-3-yl)morpholin-4-yl]ethanone —— C17H20N4O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(5-methyl-1H-1,2,4-triazol-3-yl)morpholin-4-yl]ethanone
    —— [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C19H23N3O3
    [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C17H18FN3O3
    [(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C19H23N3O3
    [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C19H23N3O3
    [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C17H18FN3O3
    [(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C19H23N3O3
    [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C17H18FN3O3
    [(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C17H18FN3O3
    [(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone