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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
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[2-(1-methylpyrazol-4-yl)ethyl]urea —— C16H20N4O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[2-(1-methylpyrazol-4-yl)ethyl]urea
    —— (2R)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-ethylpiperidine-1-carboxamide —— C17H24N2O2
    (2R)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-ethylpiperidine-1-carboxamide
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[1-(2-methoxyethyl)pyrazol-4-yl]urea —— C16H20N4O3
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[1-(2-methoxyethyl)pyrazol-4-yl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(3-methylpyridin-2-yl)urea —— C16H17N3O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(3-methylpyridin-2-yl)urea
    —— 1-[(4-bromothiophen-2-yl)methyl]-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylurea —— C16H17BrN2O2S
    1-[(4-bromothiophen-2-yl)methyl]-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylurea
    —— 3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-1-methylurea —— C17H21N3O3
    3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-1-methylurea
    —— 1-(cyclopropylmethyl)-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-propylurea —— C17H24N2O2
    1-(cyclopropylmethyl)-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-propylurea
    —— 1-[(4-cyanophenyl)methyl]-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[2-(dimethylamino)ethyl]urea —— C22H26N4O2
    1-[(4-cyanophenyl)methyl]-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[2-(dimethylamino)ethyl]urea
    —— 1-cyclohexyl-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylurea —— C17H24N2O2
    1-cyclohexyl-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylurea
    —— 3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[2-(dimethylamino)ethyl]-1-(2-methylpropyl)urea —— C18H29N3O2
    3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[2-(dimethylamino)ethyl]-1-(2-methylpropyl)urea
    —— 3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[2-(dimethylamino)ethyl]-1-(2-methylpropyl)urea —— C18H29N3O2
    3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[2-(dimethylamino)ethyl]-1-(2-methylpropyl)urea
    —— (2S)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide —— C19H21N3O2
    (2S)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide
    —— (2R)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide —— C19H21N3O2
    (2R)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(1S)-1-(4-methyl-1,2,4-triazol-3-yl)ethyl]urea —— C15H19N5O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(1S)-1-(4-methyl-1,2,4-triazol-3-yl)ethyl]urea
    —— (2S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide —— C19H21N3O2
    (2S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide
    —— 1-[(4-bromothiophen-2-yl)methyl]-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylurea —— C16H17BrN2O2S
    1-[(4-bromothiophen-2-yl)methyl]-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylurea
    —— 3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]urea —— C16H19N3O3
    3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]urea
    —— (2R)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide —— C19H21N3O2
    (2R)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-pyridin-4-ylpyrrolidine-1-carboxamide
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[2-(1-methylpyrazol-4-yl)ethyl]urea —— C16H20N4O2
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[2-(1-methylpyrazol-4-yl)ethyl]urea
    —— 2-[4-[[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylamino]methyl]-2-methoxyphenoxy]-N-ethylacetamide —— C21H26N2O4
    2-[4-[[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylamino]methyl]-2-methoxyphenoxy]-N-ethylacetamide
    —— (2S)-5-chloro-N-[[3-methoxy-4-[[(2R)-oxolan-2-yl]methoxy]phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H24ClNO5
    (2S)-5-chloro-N-[[3-methoxy-4-[[(2R)-oxolan-2-yl]methoxy]phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[[3-methoxy-4-[[(2R)-oxolan-2-yl]methoxy]phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H24ClNO5
    (2R)-5-chloro-N-[[3-methoxy-4-[[(2R)-oxolan-2-yl]methoxy]phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[3-[methyl(2,2,2-trifluoroethyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H18ClF3N2O2
    (2S)-5-chloro-N-[3-[methyl(2,2,2-trifluoroethyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S,6S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,6-dimethylmorpholine-4-sulfonamide —— C15H22N2O4S
    (2S,6S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,6-dimethylmorpholine-4-sulfonamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]methanesulfonamide —— C10H13NO3S
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]methanesulfonamide
    —— 2-methoxyethyl 5-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamoyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate —— C20H24N2O5
    2-methoxyethyl 5-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamoyl]-2,4-dimethyl-1H-pyrrole-3-carboxylate
    —— (2R,6S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,6-dimethylmorpholine-4-sulfonamide —— C15H22N2O4S
    (2R,6S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,6-dimethylmorpholine-4-sulfonamide
    —— (2R,6R)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,6-dimethylmorpholine-4-sulfonamide —— C15H22N2O4S
    (2R,6R)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,6-dimethylmorpholine-4-sulfonamide
    —— N-[1-(5-methyl-1,2,4-oxadiazol-3-yl)cyclohexyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C17H21N3O4S
    N-[1-(5-methyl-1,2,4-oxadiazol-3-yl)cyclohexyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)butanamide —— C16H19N3O3
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)butanamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)butanamide —— C18H23N3O3
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)butanamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)butanamide —— C18H23N3O3
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)butanamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)butanamide —— C16H19N3O3
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)butanamide
    —— (2R)-5-chloro-N-[(2-cyclopentyloxypyridin-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H21ClN2O3
    (2R)-5-chloro-N-[(2-cyclopentyloxypyridin-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-imidazol-1-ylpropan-1-one —— C19H24N4O2
    (2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-imidazol-1-ylpropan-1-one
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methoxyphenyl)methoxy]acetamide —— C22H27NO5
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methoxyphenyl)methoxy]acetamide
    —— (2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-imidazol-1-ylpropan-1-one —— C19H24N4O2
    (2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-imidazol-1-ylpropan-1-one
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methoxyphenyl)methoxy]acetamide —— C22H27NO5
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methoxyphenyl)methoxy]acetamide
    —— N-[(2S)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C18H24N2O3S2
    N-[(2S)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(2R)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C18H24N2O3S2
    N-[(2R)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[(1S)-1-(3,4,5-trimethoxyphenyl)ethyl]acetamide —— C21H25NO5
    2-(2,3-dihydro-1-benzofuran-5-yl)-N-[(1S)-1-(3,4,5-trimethoxyphenyl)ethyl]acetamide
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[[4-[2-(dimethylamino)-2-oxoethoxy]-3-methoxyphenyl]methyl]acetamide —— C22H26N2O5
    2-(2,3-dihydro-1-benzofuran-5-yl)-N-[[4-[2-(dimethylamino)-2-oxoethoxy]-3-methoxyphenyl]methyl]acetamide
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]methyl]acetamide —— C22H27N3O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-N-[[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]methyl]acetamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)propanamide —— C17H19N3O4
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)propanamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)propanamide —— C17H19N3O4
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)propanamide
    —— (2S)-5-chloro-N-(1-pyridin-2-ylpiperidin-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H20ClN3O2
    (2S)-5-chloro-N-(1-pyridin-2-ylpiperidin-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-(1-pyridin-2-ylpiperidin-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H20ClN3O2
    (2R)-5-chloro-N-(1-pyridin-2-ylpiperidin-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N'-pyrimidin-2-yl-2,3-dihydro-1-benzofuran-2-carbohydrazide —— C13H11ClN4O2
    (2R)-5-chloro-N'-pyrimidin-2-yl-2,3-dihydro-1-benzofuran-2-carbohydrazide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-nitroimidazo[2,1-b][1,3]thiazol-6-amine —— C14H12N4O3S
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-nitroimidazo[2,1-b][1,3]thiazol-6-amine
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-[(5Z)-2,4-dioxo-5-(pyridin-3-ylmethylidene)-1,3-thiazolidin-3-yl]ethyl]acetamide —— C23H23N3O5S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-[(5Z)-2,4-dioxo-5-(pyridin-3-ylmethylidene)-1,3-thiazolidin-3-yl]ethyl]acetamide