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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)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine —— C16H23NO4S
    (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolan-3-amine
    —— 1-[(5-chlorothiophen-2-yl)methyl]-3-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]urea —— C16H17ClN2O2S
    1-[(5-chlorothiophen-2-yl)methyl]-3-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]urea
    —— (2R)-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-thiophen-2-ylpyrrolidine-1-carboxamide —— C19H22N2O2S
    (2R)-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-thiophen-2-ylpyrrolidine-1-carboxamide
    —— 1-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-(2,2,2-trifluoroethyl)urea —— C13H15F3N2O2
    1-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-(2,2,2-trifluoroethyl)urea
    —— N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-1-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methanesulfonamide —— C21H22N2O4S
    N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-1-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methanesulfonamide
    —— N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]azepane-1-sulfonamide —— C16H24N2O3S
    N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]azepane-1-sulfonamide
    —— 6-chloro-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrazin-2-amine —— C14H14ClN3O
    6-chloro-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrazin-2-amine
    —— N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-4-(trifluoromethyl)pyrimidin-2-amine —— C20H16F3N3O
    N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-4-(trifluoromethyl)pyrimidin-2-amine
    —— 4-chloro-5-[[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]amino]-2-phenylpyridazin-3-one —— C20H18ClN3O2
    4-chloro-5-[[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]amino]-2-phenylpyridazin-3-one
    —— N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-5-nitroimidazo[2,1-b][1,3]thiazol-6-amine —— C15H14N4O3S
    N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-5-nitroimidazo[2,1-b][1,3]thiazol-6-amine
    —— (2S)-5-ethoxy-2-methyl-6-[[[methyl(propan-2-yl)sulfamoyl]amino]methyl]-2,3-dihydro-1-benzofuran —— C16H26N2O4S
    (2S)-5-ethoxy-2-methyl-6-[[[methyl(propan-2-yl)sulfamoyl]amino]methyl]-2,3-dihydro-1-benzofuran
    —— 1-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-[(1S)-1-phenylethyl]thiourea —— C19H22N2OS
    1-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-[(1S)-1-phenylethyl]thiourea
    —— [(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylideneamino]urea —— C13H17N3O3
    [(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylideneamino]urea
    —— (E)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]prop-2-enenitrile —— C20H16ClF3N2O2
    (E)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]prop-2-enenitrile
    —— 1-cyclohexyl-3-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]thiourea —— C17H24N2OS
    1-cyclohexyl-3-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]thiourea
    —— 1-amino-3-[(Z)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino]thiourea —— C11H14N4OS
    1-amino-3-[(Z)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino]thiourea
    —— 3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]urea —— C21H24N2O4
    3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-[(2-hydroxyphenyl)methyl]-1-[[(2S)-oxolan-2-yl]methyl]urea
    —— 3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-ethyl-1-(2-methylprop-2-enyl)urea —— C15H20N2O2
    3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-ethyl-1-(2-methylprop-2-enyl)urea
    —— 3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-[[(2R)-oxolan-2-yl]methyl]-1-[[(2S)-oxolan-2-yl]methyl]urea —— C19H26N2O4
    3-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-1-[[(2R)-oxolan-2-yl]methyl]-1-[[(2S)-oxolan-2-yl]methyl]urea
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2,2,2-trifluoroethoxy)acetamide —— C16H20F3NO4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2,2,2-trifluoroethoxy)acetamide
    —— 5-(furan-2-yl)-3-hydroxy-1-[3-(1H-imidazol-1-yl)propyl]-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1,5-dihydro-2H-pyrrol-2-one —— C24H23N3O5
    5-(furan-2-yl)-3-hydroxy-1-[3-(1H-imidazol-1-yl)propyl]-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1,5-dihydro-2H-pyrrol-2-one
    —— (E)-{1-[3-(diethylammonio)propyl]-4,5-dioxo-2-(pyridin-4-yl)pyrrolidin-3-ylidene}(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate —— C26H31N3O4
    (E)-{1-[3-(diethylammonio)propyl]-4,5-dioxo-2-(pyridin-4-yl)pyrrolidin-3-ylidene}(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate
    —— N-[(2R)-2-methyl-3-piperidin-1-ylpropyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C18H26N2O2
    N-[(2R)-2-methyl-3-piperidin-1-ylpropyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— (1E)-2-methyl-1-(3-piperidin-1-yl-3H-1-benzofuran-2-ylidene)propan-2-ol —— C17H23NO2
    (1E)-2-methyl-1-(3-piperidin-1-yl-3H-1-benzofuran-2-ylidene)propan-2-ol
    —— ethyl (2E)-2-(3-hydroxy-3-methyl-1-benzofuran-2-ylidene)acetate —— C13H14O4
    ethyl (2E)-2-(3-hydroxy-3-methyl-1-benzofuran-2-ylidene)acetate
    —— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(thiophen-3-ylmethyl)ethanamine —— C15H17NOS
    (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(thiophen-3-ylmethyl)ethanamine
    —— (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(thiophen-3-ylmethyl)ethanamine —— C15H17NOS
    (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(thiophen-3-ylmethyl)ethanamine
    —— (3S)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylic acid —— C9H7BrO3
    (3S)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylic acid
    —— (3R)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylic acid —— C9H7BrO3
    (3R)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylic acid
    —— (3S)-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid —— C9H7FO3
    (3S)-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid
    —— (3R)-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid —— C9H7FO3
    (3R)-5-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid
    —— [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(2-methylphenyl)carbamate —— C18H18N2O3
    [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(2-methylphenyl)carbamate
    —— (E)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methoxyethanimine —— C11H13NO2
    (E)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methoxyethanimine
    —— (E)-1-(2,3-dihydrobenzofuran-5-yl)-3-(dimethylamino)prop-2-en-1-one —— C13H15NO2
    (E)-1-(2,3-dihydrobenzofuran-5-yl)-3-(dimethylamino)prop-2-en-1-one
    —— [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(3-methylphenyl)carbamate —— C18H18N2O3
    [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(3-methylphenyl)carbamate
    —— N-[(2S)-nonan-2-yl]-2,3-dihydro-1-benzofuran-5-amine —— C17H27NO
    N-[(2S)-nonan-2-yl]-2,3-dihydro-1-benzofuran-5-amine
    —— (Z)-N-[(4-chlorophenyl)methoxy]-1-(2,3-dihydro-1-benzofuran-5-yl)methanimine —— C16H14ClNO2
    (Z)-N-[(4-chlorophenyl)methoxy]-1-(2,3-dihydro-1-benzofuran-5-yl)methanimine
    —— N-[(2R)-nonan-2-yl]-2,3-dihydro-1-benzofuran-5-amine —— C17H27NO
    N-[(2R)-nonan-2-yl]-2,3-dihydro-1-benzofuran-5-amine
    —— (2R)-2-[(2R)-oxiran-2-yl]-2,3-dihydro-1-benzofuran —— C10H10O2
    (2R)-2-[(2R)-oxiran-2-yl]-2,3-dihydro-1-benzofuran
    —— (2R)-2-[(2S)-oxiran-2-yl]-2,3-dihydro-1-benzofuran —— C10H10O2
    (2R)-2-[(2S)-oxiran-2-yl]-2,3-dihydro-1-benzofuran
    —— (2S)-2-[(2S)-oxiran-2-yl]-2,3-dihydro-1-benzofuran —— C10H10O2
    (2S)-2-[(2S)-oxiran-2-yl]-2,3-dihydro-1-benzofuran
    —— (2S)-2-[(2R)-oxiran-2-yl]-2,3-dihydro-1-benzofuran —— C10H10O2
    (2S)-2-[(2R)-oxiran-2-yl]-2,3-dihydro-1-benzofuran
    —— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methyloctan-1-amine —— C17H27NO
    (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methyloctan-1-amine
    —— (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methyloctan-1-amine —— C17H27NO
    (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methyloctan-1-amine
    —— (2R)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile —— C13H15NO3
    (2R)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile
    —— (2S)-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile —— C13H15NO3
    (2S)-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile
    —— (2R)-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile —— C13H15NO3
    (2R)-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile
    —— (2S)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile —— C13H15NO3
    (2S)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-hydroxyacetonitrile
    —— (1S)-1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]octan-1-amine —— C17H27NO
    (1S)-1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]octan-1-amine
    —— (1S)-1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]octan-1-amine —— C17H27NO
    (1S)-1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]octan-1-amine