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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
    —— 4-[(2E,3R)-2-benzylidene-5-nitro-3H-1-benzofuran-3-yl]morpholine —— C19H18N2O4
    4-[(2E,3R)-2-benzylidene-5-nitro-3H-1-benzofuran-3-yl]morpholine
    —— 5-chloro-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylimidazole-4-sulfonamide —— C13H14ClN3O3S
    5-chloro-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylimidazole-4-sulfonamide
    —— [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[[2-(4-methoxyphenyl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl]methanone —— C26H29N3O3S
    [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[[2-(4-methoxyphenyl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl]methanone
    —— [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[[2-(4-methoxyphenyl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl]methanone —— C26H29N3O3S
    [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-[[2-(4-methoxyphenyl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl]methanone
    —— (2S,3S)-2,3-dimethyl-N-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C19H24N4O2
    (2S,3S)-2,3-dimethyl-N-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-5-methyl-1-(6-oxo-1H-pyridazin-3-yl)pyrazole-4-carboxamide —— C20H21N5O4
    N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-5-methyl-1-(6-oxo-1H-pyridazin-3-yl)pyrazole-4-carboxamide
    —— (2R,3S)-2,3-dimethyl-N-[(2-phenyl-1,3-thiazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H20N2O2S
    (2R,3S)-2,3-dimethyl-N-[(2-phenyl-1,3-thiazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3R)-2,3-dimethyl-N-(2-phenylethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C19H21NO2
    (2R,3R)-2,3-dimethyl-N-(2-phenylethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3R)-N-[(2S)-2-(4-ethoxy-3-methoxyphenyl)-2-morpholin-4-ylethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C26H34N2O5
    (2R,3R)-N-[(2S)-2-(4-ethoxy-3-methoxyphenyl)-2-morpholin-4-ylethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3S)-2,3-dimethyl-N-[2-(N-methylanilino)ethyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C20H24N2O2
    (2S,3S)-2,3-dimethyl-N-[2-(N-methylanilino)ethyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3S)-2,3-dimethyl-N-[(2S)-2-morpholin-4-yl-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H26N2O3S
    (2S,3S)-2,3-dimethyl-N-[(2S)-2-morpholin-4-yl-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3S)-2,3-dimethyl-N-(3-phenylprop-2-ynyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C20H19NO2
    (2S,3S)-2,3-dimethyl-N-(3-phenylprop-2-ynyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-2,3-dimethyl-N-(3-phenylprop-2-ynyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C20H19NO2
    (2R,3S)-2,3-dimethyl-N-(3-phenylprop-2-ynyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— [(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(2-propan-2-yliminopyridin-1-yl)methanone —— C19H22N2O2
    [(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(2-propan-2-yliminopyridin-1-yl)methanone
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-oxopyridin-1-yl)acetamide —— C19H22N2O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-oxopyridin-1-yl)acetamide
    —— (2R)-N-[5-[1-(difluoromethyl)imidazol-2-yl]-4-methyl-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H14F2N4O2S
    (2R)-N-[5-[1-(difluoromethyl)imidazol-2-yl]-4-methyl-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R,3S)-2,3-dimethyl-N-[(S)-(1-methylimidazol-2-yl)-phenylmethyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C22H23N3O2
    (2R,3S)-2,3-dimethyl-N-[(S)-(1-methylimidazol-2-yl)-phenylmethyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R)-5-chloro-N-[5-[1-(difluoromethyl)imidazol-2-yl]-4-methyl-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H13ClF2N4O2S
    (2R)-5-chloro-N-[5-[1-(difluoromethyl)imidazol-2-yl]-4-methyl-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S,3S)-2,3-dimethyl-N-[(S)-(1-methylimidazol-2-yl)-phenylmethyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C22H23N3O2
    (2S,3S)-2,3-dimethyl-N-[(S)-(1-methylimidazol-2-yl)-phenylmethyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-N-[(S)-(4-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C23H25N3O3
    (2R,3S)-N-[(S)-(4-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— 1,7-dicyclopropyl-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]pyrimido[4,5-d]pyrimidine-2,4-dione —— C24H26N4O4S
    1,7-dicyclopropyl-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]pyrimido[4,5-d]pyrimidine-2,4-dione
    —— (2S,3R)-N-[2-(5-bromothiophen-2-yl)ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C17H18BrNO2S
    (2S,3R)-N-[2-(5-bromothiophen-2-yl)ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-N-[2-(5-bromothiophen-2-yl)ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C17H18BrNO2S
    (2R,3S)-N-[2-(5-bromothiophen-2-yl)ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-morpholin-4-ylethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C24H26N2O5S
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-morpholin-4-ylethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 1-[4-cyclopropyl-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-3-yl]piperidine —— C22H30N4O2S
    1-[4-cyclopropyl-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-3-yl]piperidine
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1S)-1-(2-methoxyphenyl)ethyl]acetamide —— C21H25NO4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1S)-1-(2-methoxyphenyl)ethyl]acetamide
    —— (2S)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-6-methyl-2,3-dihydro-1-benzothiophene-2-carboxamide —— C21H23NO3S
    (2S)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-6-methyl-2,3-dihydro-1-benzothiophene-2-carboxamide
    —— (2S,3R)-N-[(6-methoxypyridin-3-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C18H20N2O3
    (2S,3R)-N-[(6-methoxypyridin-3-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— 5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1-(furan-2-ylmethyl)tetrazole —— C18H20N4O3S
    5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1-(furan-2-ylmethyl)tetrazole
    —— 3-(3,5-dimethylpyrazol-1-yl)-6-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]pyridazine —— C21H24N4O2S
    3-(3,5-dimethylpyrazol-1-yl)-6-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]pyridazine
    —— (2R)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-6-methyl-2,3-dihydro-1-benzothiophene-2-carboxamide —— C21H23NO3S
    (2R)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-6-methyl-2,3-dihydro-1-benzothiophene-2-carboxamide
    —— (E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methyl-1,3-thiazol-4-yl)prop-2-enamide —— C19H22N2O3S
    (E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methyl-1,3-thiazol-4-yl)prop-2-enamide
    —— 4-cyclopropyl-3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-propan-2-yl-1,2,4-triazole —— C20H27N3O2S
    4-cyclopropyl-3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-propan-2-yl-1,2,4-triazole
    —— [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone —— C25H29NO5
    [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(furan-2-ylmethyl)-5-propan-2-yl-1,2,4-triazole —— C22H27N3O3S
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(furan-2-ylmethyl)-5-propan-2-yl-1,2,4-triazole
    —— [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(prop-2-enylamino)-1,3-thiazole-4-carboxylate —— C19H22N2O4S
    [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(prop-2-enylamino)-1,3-thiazole-4-carboxylate
    —— 4-[4-benzyl-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-3-yl]morpholine —— C25H30N4O3S
    4-[4-benzyl-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-3-yl]morpholine
    —— 3-cyclopropyl-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-4-amine —— C17H22N4O2S
    3-cyclopropyl-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-4-amine
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(2-methylfuran-3-yl)-4-prop-2-enyl-1,2,4-triazole —— C22H25N3O3S
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(2-methylfuran-3-yl)-4-prop-2-enyl-1,2,4-triazole
    —— 5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-N-ethyl-1,3,4-thiadiazol-2-amine —— C16H21N3O2S2
    5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-N-ethyl-1,3,4-thiadiazol-2-amine
    —— 5-acetyl-2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-6-methylpyridine-3-carbonitrile —— C21H22N2O3S
    5-acetyl-2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-6-methylpyridine-3-carbonitrile
    —— 2-(2-bromophenyl)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,3,4-oxadiazole —— C20H19BrN2O3S
    2-(2-bromophenyl)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,3,4-oxadiazole
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2S)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole —— C23H27N3O3S2
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2S)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole
    —— [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(prop-2-enylamino)-1,3-thiazole-4-carboxylate —— C19H22N2O4S
    [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(prop-2-enylamino)-1,3-thiazole-4-carboxylate
    —— [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl (E)-3-(furan-2-yl)prop-2-enoate —— C19H20O5
    [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl (E)-3-(furan-2-yl)prop-2-enoate
    —— 2-(2-bromophenyl)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,3,4-oxadiazole —— C20H19BrN2O3S
    2-(2-bromophenyl)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,3,4-oxadiazole
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-methylphenyl)propanamide —— C22H27NO3
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-methylphenyl)propanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-methylphenyl)propanamide —— C22H27NO3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-methylphenyl)propanamide
    —— (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide —— C21H24FNO4
    (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide
    —— (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide —— C22H27NO4
    (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide