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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
    —— (3R)-5-bromo-N-methyl-N-[(1-methylpyrrol-2-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H17BrN2O2
    (3R)-5-bromo-N-methyl-N-[(1-methylpyrrol-2-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-[(1R)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H17BrN2O2
    (3S)-5-bromo-N-[(1R)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-(3-methyl-1,2,4-thiadiazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C12H10BrN3O2S
    (3R)-5-bromo-N-(3-methyl-1,2,4-thiadiazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 5-(difluoromethyl)-N-[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]-1-(2-methylpropyl)pyrazole-4-carboxamide —— C18H21F2N3O2
    5-(difluoromethyl)-N-[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]-1-(2-methylpropyl)pyrazole-4-carboxamide
    —— (3S)-5-bromo-N-[2-[(S)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C12H14BrNO3S
    (3S)-5-bromo-N-[2-[(S)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-[(1R)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H17BrN2O2
    (3R)-5-bromo-N-[(1R)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-methyl-N-(pyrazin-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H14BrN3O2
    (3S)-5-bromo-N-methyl-N-(pyrazin-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-methyl-N-[(1-methylpyrrol-2-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H17BrN2O2
    (3S)-5-bromo-N-methyl-N-[(1-methylpyrrol-2-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-[2-(1H-1,2,4-triazol-5-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C13H13BrN4O2
    (3S)-5-bromo-N-[2-(1H-1,2,4-triazol-5-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-(2H-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C10H8BrN5O2
    (3R)-5-bromo-N-(2H-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-[(1-methylpyrrol-3-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H15BrN2O2
    (3S)-5-bromo-N-[(1-methylpyrrol-3-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-[(1S)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H17BrN2O2
    (3S)-5-bromo-N-[(1S)-1-cyano-2,2-dimethylpropyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-(4-methylsulfanylbutyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H18BrNO2S
    (3S)-5-bromo-N-(4-methylsulfanylbutyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-(4-methylsulfanylbutyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H18BrNO2S
    (3R)-5-bromo-N-(4-methylsulfanylbutyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-methyl-N-(pyrazin-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H14BrN3O2
    (3R)-5-bromo-N-methyl-N-(pyrazin-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-[2-(1H-1,2,4-triazol-5-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C13H13BrN4O2
    (3R)-5-bromo-N-[2-(1H-1,2,4-triazol-5-yl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-(2H-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C10H8BrN5O2
    (3S)-5-bromo-N-(2H-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-[2-[(R)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C12H14BrNO3S
    (3R)-5-bromo-N-[2-[(R)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-(1H-imidazol-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C13H12BrN3O2
    (3S)-5-bromo-N-(1H-imidazol-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-[2-[(R)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C12H14BrNO3S
    (3S)-5-bromo-N-[2-[(R)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-[2-[(S)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C12H14BrNO3S
    (3R)-5-bromo-N-[2-[(S)-methylsulfinyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-(1H-imidazol-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C13H12BrN3O2
    (3R)-5-bromo-N-(1H-imidazol-2-ylmethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-5-bromo-N-methoxy-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide —— C11H12BrNO3
    (3S)-5-bromo-N-methoxy-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide
    —— [(3R)-5-bromo-2,3-dihydro-1-benzofuran-3-yl]-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methanone —— C15H14BrN3O2
    [(3R)-5-bromo-2,3-dihydro-1-benzofuran-3-yl]-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methanone
    —— (3S)-5-bromo-N-(2-pyridin-3-ylethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H15BrN2O2
    (3S)-5-bromo-N-(2-pyridin-3-ylethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— [(3S)-5-bromo-2,3-dihydro-1-benzofuran-3-yl]-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methanone —— C15H14BrN3O2
    [(3S)-5-bromo-2,3-dihydro-1-benzofuran-3-yl]-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methanone
    —— (3R)-5-bromo-N-methoxy-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide —— C11H12BrNO3
    (3R)-5-bromo-N-methoxy-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-5-bromo-N-(2-pyridin-3-ylethyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H15BrN2O2
    (3R)-5-bromo-N-(2-pyridin-3-ylethyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 1-[(1S)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea —— C18H23N3O3
    1-[(1S)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(1S)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea —— C18H23N3O3
    1-[(1S)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(1R)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea —— C18H23N3O3
    1-[(1R)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(1R)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea —— C18H23N3O3
    1-[(1R)-1-(3,5-dimethyl-1,2-oxazol-4-yl)propyl]-3-[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1R)-1-[(2S)-oxolan-2-yl]propyl]urea —— C16H22N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1R)-1-[(2S)-oxolan-2-yl]propyl]urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1R)-1-[(2R)-oxolan-2-yl]propyl]urea —— C16H22N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1R)-1-[(2R)-oxolan-2-yl]propyl]urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1S)-1-[(2R)-oxolan-2-yl]propyl]urea —— C16H22N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1S)-1-[(2R)-oxolan-2-yl]propyl]urea
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1S)-1-[(2S)-oxolan-2-yl]propyl]urea —— C16H22N2O3
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[(1S)-1-[(2S)-oxolan-2-yl]propyl]urea
    —— 4-acetyl-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thiophene-2-carboxamide —— C17H17NO3S
    4-acetyl-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thiophene-2-carboxamide
    —— 4-acetyl-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thiophene-2-carboxamide —— C17H17NO3S
    4-acetyl-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thiophene-2-carboxamide
    —— N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide —— C19H24N4O2
    N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide
    —— (3R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[[ethyl(methyl)amino]methyl]pyrrolidine-1-carboxamide —— C19H29N3O2
    (3R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[[ethyl(methyl)amino]methyl]pyrrolidine-1-carboxamide
    —— N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide —— C16H19N3O2S
    N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide
    —— N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide —— C19H24N4O2
    N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide
    —— 1-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[2-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)ethyl]urea —— C18H23N5O2
    1-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[2-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)ethyl]urea
    —— 4-acetyl-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thiophene-2-carboxamide —— C17H17NO3S
    4-acetyl-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thiophene-2-carboxamide
    —— N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide —— C16H19N3O2S
    N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide
    —— N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide —— C16H19N3O2S
    N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide
    —— N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide —— C16H19N3O2S
    N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-methyl-5-(methylamino)-1,2-thiazole-4-carboxamide
    —— N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide —— C19H24N4O2
    N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide
    —— N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide —— C19H24N4O2
    N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-4-(1H-pyrazol-5-yl)piperidine-1-carboxamide
    —— (3S)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[[ethyl(methyl)amino]methyl]pyrrolidine-1-carboxamide —— C19H29N3O2
    (3S)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]-3-[[ethyl(methyl)amino]methyl]pyrrolidine-1-carboxamide