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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
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C17H18ClN3O3
    [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C17H18ClN3O3
    [(2S)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-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]-[(2S)-2-(5-methyl-1H-1,2,4-triazol-3-yl)morpholin-4-yl]methanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone —— C18H21N3O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone
    —— [(2R)-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
    [(2R)-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)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C17H18FN3O3
    [(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C16H16FN3O3
    [(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone —— C18H21N3O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone
    —— [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C16H16FN3O3
    [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C18H21N3O3
    [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C17H18FN3O3
    [(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C18H21N3O3
    [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C16H16FN3O3
    [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C17H19N3O3
    [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C16H16FN3O3
    [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C16H16FN3O3
    [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C17H19N3O3
    [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C18H21N3O3
    [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C17H19N3O3
    [(3S)-2,3-dihydro-1-benzofuran-3-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)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone —— C17H18FN3O3
    [(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanone
    —— [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C17H19N3O3
    [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2S)-2-(5-ethyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C16H16FN3O3
    [(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone —— C17H19N3O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone
    —— [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone —— C16H16FN3O3
    [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]methanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone —— C17H19N3O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]ethanone
    —— (4R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-ethyl-4,5,6,7-tetrahydroindazol-4-amine —— C18H23N3O
    (4R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-ethyl-4,5,6,7-tetrahydroindazol-4-amine
    —— (4R)-1-ethyl-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,5,6,7-tetrahydroindazol-4-amine —— C20H27N3O2
    (4R)-1-ethyl-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,5,6,7-tetrahydroindazol-4-amine
    —— (4S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-ethyl-4,5,6,7-tetrahydroindazol-4-amine —— C18H23N3O
    (4S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-ethyl-4,5,6,7-tetrahydroindazol-4-amine
    —— (1R)-1-[(2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C11H15NO
    (1R)-1-[(2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— (1R)-1-[(2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C11H15NO
    (1R)-1-[(2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— (1R)-1-[(2R,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-yl]ethanamine —— C11H15NO
    (1R)-1-[(2R,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-yl]ethanamine
    —— (2R)-5-fluoro-N-[1-(pyridin-3-ylmethyl)-1,2,4-triazol-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H14FN5O2
    (2R)-5-fluoro-N-[1-(pyridin-3-ylmethyl)-1,2,4-triazol-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-fluoro-N-(5-pyridin-2-yl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H11FN4O2S
    (2S)-5-fluoro-N-(5-pyridin-2-yl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-fluoro-N-[1-(pyridin-3-ylmethyl)-1,2,4-triazol-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H14FN5O2
    (2S)-5-fluoro-N-[1-(pyridin-3-ylmethyl)-1,2,4-triazol-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-fluoro-N-(5-pyridin-2-yl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H11FN4O2S
    (2R)-5-fluoro-N-(5-pyridin-2-yl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole —— C14H17N3O2
    1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole
    —— 1-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole —— C14H17N3O2
    1-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole
    —— (2S)-N-[(2R)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18N2O2S
    (2S)-N-[(2R)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2R)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18N2O2S
    (2R)-N-[(2R)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(2S)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18N2O2S
    (2S)-N-[(2S)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2S)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18N2O2S
    (2R)-N-[(2S)-2-(1,3-thiazol-2-yl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(1-pyrimidin-2-ylpyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H13N5O2
    (2R)-N-(1-pyrimidin-2-ylpyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-(1-pyrimidin-2-ylpyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H13N5O2
    (2S)-N-(1-pyrimidin-2-ylpyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-methylphenoxy)acetamide —— C21H25NO4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-methylphenoxy)acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-methylphenoxy)acetamide —— C21H25NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-methylphenoxy)acetamide
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-2-(dimethylamino)-2-(1-methylpyrazol-4-yl)ethyl]urea —— C17H23N5O2
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-2-(dimethylamino)-2-(1-methylpyrazol-4-yl)ethyl]urea
    —— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-2-(dimethylamino)-2-(1-methylpyrazol-4-yl)ethyl]urea —— C17H23N5O2
    1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-2-(dimethylamino)-2-(1-methylpyrazol-4-yl)ethyl]urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-2-(dimethylamino)-2-(1-methylpyrazol-4-yl)ethyl]urea —— C17H23N5O2
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-2-(dimethylamino)-2-(1-methylpyrazol-4-yl)ethyl]urea
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-[(S)-methylsulfinyl]ethanamine —— C12H17NO2S
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-[(S)-methylsulfinyl]ethanamine
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-[(R)-methylsulfinyl]ethanamine —— C12H17NO2S
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-[(R)-methylsulfinyl]ethanamine