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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-[[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-phenoxyacetamide —— C17H16FNO3
    N-[[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-phenoxyacetamide
    —— methyl (2S)-2-[[[(E)-but-2-enoyl]amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate —— C15H17NO4
    methyl (2S)-2-[[[(E)-but-2-enoyl]amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate
    —— methyl (2S)-2-[[(3-methoxy-3-oxopropanoyl)amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate —— C15H17NO6
    methyl (2S)-2-[[(3-methoxy-3-oxopropanoyl)amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate
    —— N-[[(2S)-5-tert-butyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-cyclopentylpropanamide —— C21H31NO2
    N-[[(2S)-5-tert-butyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-cyclopentylpropanamide
    —— methyl (2S)-2-[[[(2S)-2-chloropropanoyl]amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate —— C14H16ClNO4
    methyl (2S)-2-[[[(2S)-2-chloropropanoyl]amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate
    —— 5-chloro-N-[[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]pentanamide —— C14H17ClFNO2
    5-chloro-N-[[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]pentanamide
    —— methyl 5-[[(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methylamino]-5-oxopentanoate —— C15H18FNO4
    methyl 5-[[(2R)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methylamino]-5-oxopentanoate
    —— methyl (2S)-2-[[[(2R)-2-ethylhexanoyl]amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate —— C19H27NO4
    methyl (2S)-2-[[[(2R)-2-ethylhexanoyl]amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate
    —— 5-chloro-N-[[(2S)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl]pentanamide —— C15H20ClNO3
    5-chloro-N-[[(2S)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl]pentanamide
    —— methyl (2R)-2-[[(2-methoxyacetyl)amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate —— C14H17NO5
    methyl (2R)-2-[[(2-methoxyacetyl)amino]methyl]-2,3-dihydro-1-benzofuran-5-carboxylate
    —— N-[[(2R)-5-tert-butyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-cyclopentylpropanamide —— C21H31NO2
    N-[[(2R)-5-tert-butyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-cyclopentylpropanamide
    —— 3-hydroxy-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-1-(2-phenylethyl)-5-(pyridin-4-yl)-2,5-dihydro-1H-pyrrol-2-one —— C27H24N2O4
    3-hydroxy-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-1-(2-phenylethyl)-5-(pyridin-4-yl)-2,5-dihydro-1H-pyrrol-2-one
    —— 3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1-(2-phenylethyl)-5-(pyridin-4-yl)-1,5-dihydro-2H-pyrrol-2-one —— C27H24N2O4
    3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-1-(2-phenylethyl)-5-(pyridin-4-yl)-1,5-dihydro-2H-pyrrol-2-one
    —— (4E)-1-benzyl-5-(furan-2-yl)-4-[hydroxy(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione —— C25H21NO5
    (4E)-1-benzyl-5-(furan-2-yl)-4-[hydroxy(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione
    —— (S)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl-[(2R)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H19NO3
    (S)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl-[(2R)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— (S)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl-[(2S)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H19NO3
    (S)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl-[(2S)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— 1-[2-(dimethylamino)ethyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methylfuran-2-yl)-1,5-dihydro-2H-pyrrol-2-one —— C23H26N2O5
    1-[2-(dimethylamino)ethyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methylfuran-2-yl)-1,5-dihydro-2H-pyrrol-2-one
    —— 3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methyl-2-furyl)-1-(2-phenylethyl)-1,5-dihydro-2H-pyrrol-2-one —— C27H25NO5
    3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methyl-2-furyl)-1-(2-phenylethyl)-1,5-dihydro-2H-pyrrol-2-one
    —— (5Z)-3-methyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H13NO2S2
    (5Z)-3-methyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (3R)-3-[3-(N-methylanilino)propylamino]-2,3-dihydro-1-benzofuran-6-ol —— C18H22N2O2
    (3R)-3-[3-(N-methylanilino)propylamino]-2,3-dihydro-1-benzofuran-6-ol
    —— 5-[(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methylene]-3-(tetrahydro-2-furanylmethyl)-2-thioxo-1,3-thiazolidin-4-one —— C18H19NO3S2
    5-[(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methylene]-3-(tetrahydro-2-furanylmethyl)-2-thioxo-1,3-thiazolidin-4-one
    —— 3-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C16H15NO4S2
    3-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
    —— (5Z)-3-cyclopentyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H19NO2S2
    (5Z)-3-cyclopentyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (5Z)-3-benzyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H17NO2S2
    (5Z)-3-benzyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (5Z)-3-(furan-2-ylmethyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
    (5Z)-3-(furan-2-ylmethyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-3-(1-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C21H19NO2S2
    (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-3-(1-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
    —— 2-{5-[(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methylene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}ethanesulfonic acid —— C15H15NO5S3
    2-{5-[(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methylene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}ethanesulfonic acid
    —— (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-3-(2-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C21H19NO2S2
    (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-3-(2-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (4E)-1-benzyl-4-[hydroxy(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione —— C26H23NO5
    (4E)-1-benzyl-4-[hydroxy(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione
    —— (5Z)-3-(2-methoxyethyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H17NO3S2
    (5Z)-3-(2-methoxyethyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— 1-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperidine-4-carboxamide —— C19H21N3O3S
    1-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperidine-4-carboxamide
    —— 3-Isobutyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylene]-2-thioxo-1,3-thiazolidin-4-one —— C17H19NO2S2
    3-Isobutyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylene]-2-thioxo-1,3-thiazolidin-4-one
    —— (5Z)-3-[2-(4-methoxyphenyl)ethyl]-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one —— C22H21NO3S2
    (5Z)-3-[2-(4-methoxyphenyl)ethyl]-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one
    —— (5Z)-3-(4-methoxybenzyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one —— C21H19NO3S2
    (5Z)-3-(4-methoxybenzyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one
    —— (5Z)-3-(4-fluorobenzyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one —— C20H16FNO2S2
    (5Z)-3-(4-fluorobenzyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one
    —— (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one —— C17H18N2O3S
    (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one
    —— (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanyl-1,3-thiazol-4(5H)-one —— C13H11NO2S2
    (5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanyl-1,3-thiazol-4(5H)-one
    —— 4-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C17H17NO4S2
    4-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
    —— (5Z)-2-(4-benzylpiperazin-1-yl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1,3-thiazol-4-one —— C24H25N3O2S
    (5Z)-2-(4-benzylpiperazin-1-yl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1,3-thiazol-4-one
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-phenylmethanamine —— C19H23NO2
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-phenylmethanamine
    —— (5Z)-3-(3-methoxypropyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H19NO3S2
    (5Z)-3-(3-methoxypropyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— 4-[(5Z)-5-[(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C19H21NO5S2
    4-[(5Z)-5-[(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
    —— 5-[(5Z)-5-[(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C20H23NO5S2
    5-[(5Z)-5-[(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
    —— 3-[(5Z)-5-[(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C18H19NO5S2
    3-[(5Z)-5-[(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
    —— [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C9H10FNO
    [(2S)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— (3R)-N-cyclopentyl-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]pyrrolidine-3-carboxamide —— C21H30N2O2
    (3R)-N-cyclopentyl-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]pyrrolidine-3-carboxamide
    —— (3R)-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]-N-pyridin-2-ylpyrrolidine-3-carboxamide —— C21H25N3O2
    (3R)-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]-N-pyridin-2-ylpyrrolidine-3-carboxamide
    —— (3S)-N-[2-[5-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]ethyl]-1,1-dioxothiolan-3-amine —— C19H25N3O3S
    (3S)-N-[2-[5-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]ethyl]-1,1-dioxothiolan-3-amine
    —— 5-(1-ethylpyrazol-4-yl)-N-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-1,2-oxazole-3-carboxamide —— C20H22N4O3
    5-(1-ethylpyrazol-4-yl)-N-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-1,2-oxazole-3-carboxamide
    —— 4-[(2R)-2-[5-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]propyl]morpholine —— C20H27N3O2
    4-[(2R)-2-[5-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]propyl]morpholine