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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
    —— N-[(1S,3R)-3-methylcyclohexyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C16H21NO2
    N-[(1S,3R)-3-methylcyclohexyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[3-[[(2R)-oxolan-2-yl]methoxy]propyl]urea —— C18H26N2O4
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[3-[[(2R)-oxolan-2-yl]methoxy]propyl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[3-[[(2S)-oxolan-2-yl]methoxy]propyl]urea —— C18H26N2O4
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[3-[[(2S)-oxolan-2-yl]methoxy]propyl]urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[3-[[(2R)-oxolan-2-yl]methoxy]propyl]urea —— C18H26N2O4
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[3-[[(2R)-oxolan-2-yl]methoxy]propyl]urea
    —— N-[[(3R)-1,1-dioxothiolan-3-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C14H17NO4S
    N-[[(3R)-1,1-dioxothiolan-3-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[[(3S)-1,1-dioxothiolan-3-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C14H17NO4S
    N-[[(3S)-1,1-dioxothiolan-3-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— [(2S)-2-benzylpyrrolidin-1-yl]-(2,3-dihydro-1-benzofuran-5-yl)methanone —— C20H21NO2
    [(2S)-2-benzylpyrrolidin-1-yl]-(2,3-dihydro-1-benzofuran-5-yl)methanone
    —— [4-(2,3-dihydro-1-benzofuran-5-carbonyl)piperazin-1-yl]-[(2R)-oxolan-2-yl]methanone —— C18H22N2O4
    [4-(2,3-dihydro-1-benzofuran-5-carbonyl)piperazin-1-yl]-[(2R)-oxolan-2-yl]methanone
    —— [4-(2,3-dihydro-1-benzofuran-5-carbonyl)piperazin-1-yl]-[(2S)-oxolan-2-yl]methanone —— C18H22N2O4
    [4-(2,3-dihydro-1-benzofuran-5-carbonyl)piperazin-1-yl]-[(2S)-oxolan-2-yl]methanone
    —— 2-[[4-ethyl-5-[(2-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C23H26N4O4S
    2-[[4-ethyl-5-[(2-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
    —— 2-[[5-[(1R)-1-(3-chlorophenoxy)ethyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C23H25ClN4O4S
    2-[[5-[(1R)-1-(3-chlorophenoxy)ethyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
    —— N-[(3S)-5-chloro-2,3-dihydro-1-benzofuran-3-yl]-2-[[4-ethyl-5-[(2-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]acetamide —— C22H23ClN4O3S
    N-[(3S)-5-chloro-2,3-dihydro-1-benzofuran-3-yl]-2-[[4-ethyl-5-[(2-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]acetamide
    —— 2-[[4-ethyl-5-[(1R)-1-phenylethyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C23H26N4O3S
    2-[[4-ethyl-5-[(1R)-1-phenylethyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
    —— 2-[[4-ethyl-5-[(1S)-1-phenylethyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C23H26N4O3S
    2-[[4-ethyl-5-[(1S)-1-phenylethyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
    —— 2-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C14H16N2O3S2
    2-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
    —— 2-[[4-ethyl-5-[(4-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C23H26N4O4S
    2-[[4-ethyl-5-[(4-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]-N-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
    —— N-[(3S)-5-chloro-2,3-dihydro-1-benzofuran-3-yl]-2-[[4-ethyl-5-[(4-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]acetamide —— C22H23ClN4O3S
    N-[(3S)-5-chloro-2,3-dihydro-1-benzofuran-3-yl]-2-[[4-ethyl-5-[(4-methylphenoxy)methyl]-1,2,4-triazol-3-yl]sulfanyl]acetamide
    —— 2-[[5-[(1R)-1-(3-chlorophenoxy)ethyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]-N-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C23H25ClN4O4S
    2-[[5-[(1R)-1-(3-chlorophenoxy)ethyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]-N-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
    —— [2-[[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]amino]-2-oxoethyl] N,N-diethylcarbamodithioate —— C16H22N2O3S2
    [2-[[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]amino]-2-oxoethyl] N,N-diethylcarbamodithioate
    —— N-[(3R)-5-chloro-2,3-dihydro-1-benzofuran-3-yl]-2-[[5-[(2-chlorophenoxy)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetamide —— C21H20Cl2N4O3S
    N-[(3R)-5-chloro-2,3-dihydro-1-benzofuran-3-yl]-2-[[5-[(2-chlorophenoxy)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]acetamide
    —— [2-[[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]amino]-2-oxoethyl] N,N-diethylcarbamodithioate —— C16H22N2O3S2
    [2-[[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]amino]-2-oxoethyl] N,N-diethylcarbamodithioate
    —— (5Z)-3-(2-methoxyethyl)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H17NO3S2
    (5Z)-3-(2-methoxyethyl)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (2R)-5-chloro-N-[(4-ethyl-1,2,4-triazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H15ClN4O2
    (2R)-5-chloro-N-[(4-ethyl-1,2,4-triazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(2R)-1-morpholin-4-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C15H22N2O4S
    N-[(2R)-1-morpholin-4-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(2R)-1-pyrazol-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C14H17N3O3S
    N-[(2R)-1-pyrazol-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(2S)-2-morpholin-4-yl-2-[(3S)-oxolan-3-yl]ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C19H26N2O4
    N-[(2S)-2-morpholin-4-yl-2-[(3S)-oxolan-3-yl]ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[(2R)-2-morpholin-4-yl-2-[(3R)-oxolan-3-yl]ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C19H26N2O4
    N-[(2R)-2-morpholin-4-yl-2-[(3R)-oxolan-3-yl]ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 3-[(5Z)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C16H14NO4S2-
    3-[(5Z)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
    —— (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide —— C18H24N2O4
    (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide
    —— (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide —— C18H24N2O4
    (3R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide
    —— (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide —— C18H24N2O4
    (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide
    —— (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide —— C18H24N2O4
    (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methyl-5-oxopyrrolidine-3-carboxamide
    —— 1-[(2R,3S)-3-hydroxy-2-(1,2,4-triazol-1-yl)-3H-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one —— C15H17N3O3
    1-[(2R,3S)-3-hydroxy-2-(1,2,4-triazol-1-yl)-3H-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one
    —— 1-[(2S,3R)-3-hydroxy-2-(1,2,4-triazol-1-yl)-3H-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one —— C15H17N3O3
    1-[(2S,3R)-3-hydroxy-2-(1,2,4-triazol-1-yl)-3H-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one
    —— (1R,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(trifluoromethyl)cyclohexane-1-carboxamide —— C20H26F3NO3
    (1R,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(trifluoromethyl)cyclohexane-1-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-ethylsulfanylpropanamide —— C17H25NO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-ethylsulfanylpropanamide
    —— (5E)-3-benzyl-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H17NO2S2
    (5E)-3-benzyl-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (1S,2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(trifluoromethyl)cyclohexane-1-carboxamide —— C20H26F3NO3
    (1S,2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(trifluoromethyl)cyclohexane-1-carboxamide
    —— (5Z)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[(1S)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C21H19NO2S2
    (5Z)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[(1S)-1-phenylethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— N-[2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylcarbamoylamino]ethyl]acetamide —— C17H25N3O4
    N-[2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylcarbamoylamino]ethyl]acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-hydroxypiperidine-1-carboxamide —— C18H26N2O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-hydroxypiperidine-1-carboxamide
    —— (2S)-5-chloro-N-(2-imidazol-1-ylethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H14ClN3O2
    (2S)-5-chloro-N-(2-imidazol-1-ylethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(pyridin-2-ylmethyl)urea —— C19H23N3O3
    1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(pyridin-2-ylmethyl)urea
    —— 1-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(pyridin-2-ylmethyl)urea —— C19H23N3O3
    1-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(pyridin-2-ylmethyl)urea
    —— 2-(3,5-dimethylpyrazol-1-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C19H25N3O3
    2-(3,5-dimethylpyrazol-1-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— N-[(1R)-1-pyridin-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C15H16N2O3S
    N-[(1R)-1-pyridin-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(1S)-1-pyridin-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C15H16N2O3S
    N-[(1S)-1-pyridin-3-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— 1-[(3S)-1,1-dioxothiolan-3-yl]-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine —— C16H23NO4S
    1-[(3S)-1,1-dioxothiolan-3-yl]-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine
    —— N-[(1S)-1-pyridin-4-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C15H16N2O3S
    N-[(1S)-1-pyridin-4-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— 1-[(3R)-1,1-dioxothiolan-3-yl]-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine —— C16H23NO4S
    1-[(3R)-1,1-dioxothiolan-3-yl]-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine