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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
    —— (2R)-5-chloro-N-[3-(thiophene-2-carbonylamino)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H17ClN2O3S
    (2R)-5-chloro-N-[3-(thiophene-2-carbonylamino)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(S)-cyclopentyl(thiophen-2-yl)methyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C18H21NO3S2
    N-[(S)-cyclopentyl(thiophen-2-yl)methyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(R)-cyclopentyl(thiophen-2-yl)methyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C18H21NO3S2
    N-[(R)-cyclopentyl(thiophen-2-yl)methyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (3R)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-3-hydroxypiperidine-1-carboxamide —— C21H24N2O3
    (3R)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-3-hydroxypiperidine-1-carboxamide
    —— (3S)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-3-(hydroxymethyl)piperidine-1-carboxamide —— C22H26N2O3
    (3S)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-3-(hydroxymethyl)piperidine-1-carboxamide
    —— (2S)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-1,4-dioxane-2-carboxamide —— C20H21NO4
    (2S)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-1,4-dioxane-2-carboxamide
    —— 2-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethanimidamide —— C10H12N2O
    2-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethanimidamide
    —— 2-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethanimidamide —— C10H12N2O
    2-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethanimidamide
    —— (2R)-7-fluoro-N-(5-hydroxy-4,4-dimethylpentyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H22FNO3
    (2R)-7-fluoro-N-(5-hydroxy-4,4-dimethylpentyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-7-fluoro-N-(5-hydroxy-4,4-dimethylpentyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H22FNO3
    (2S)-7-fluoro-N-(5-hydroxy-4,4-dimethylpentyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 5-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylsulfanyl]-1-methyltetrazole —— C11H12N4OS
    5-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylsulfanyl]-1-methyltetrazole
    —— 5-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methylsulfanyl]-1-methyltetrazole —— C11H12N4OS
    5-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methylsulfanyl]-1-methyltetrazole
    —— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[[2-(2-methylimidazol-1-yl)pyridin-4-yl]methyl]urea —— C19H19N5O2
    1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[[2-(2-methylimidazol-1-yl)pyridin-4-yl]methyl]urea
    —— (3S)-1-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-N-(3-methylpyridin-2-yl)piperidine-1,3-dicarboxamide —— C21H24N4O3
    (3S)-1-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-N-(3-methylpyridin-2-yl)piperidine-1,3-dicarboxamide
    —— (3R)-1-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-N-(3-methylpyridin-2-yl)piperidine-1,3-dicarboxamide —— C21H24N4O3
    (3R)-1-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-N-(3-methylpyridin-2-yl)piperidine-1,3-dicarboxamide
    —— (3R)-1-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-N-(3-methylpyridin-2-yl)piperidine-1,3-dicarboxamide —— C21H24N4O3
    (3R)-1-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-N-(3-methylpyridin-2-yl)piperidine-1,3-dicarboxamide
    —— (3R)-N-(cyclopropylmethyl)-N-(3,3,3-trifluoropropyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H18F3NO2
    (3R)-N-(cyclopropylmethyl)-N-(3,3,3-trifluoropropyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-(cyclopropylmethyl)-N-(3,3,3-trifluoropropyl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H18F3NO2
    (3S)-N-(cyclopropylmethyl)-N-(3,3,3-trifluoropropyl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— tert-butyl N-[1-[5-[(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]cyclobutyl]carbamate —— C19H22ClN3O4
    tert-butyl N-[1-[5-[(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]cyclobutyl]carbamate
    —— tert-butyl N-[1-[5-[(2S)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]cyclobutyl]carbamate —— C19H22ClN3O4
    tert-butyl N-[1-[5-[(2S)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]cyclobutyl]carbamate
    —— N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-5-(2,5-dimethylpyrrol-1-yl)-1-methylpyrazole-4-carboxamide —— C19H20N4O2
    N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-5-(2,5-dimethylpyrrol-1-yl)-1-methylpyrazole-4-carboxamide
    —— N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-1-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methanesulfonamide —— C21H22N2O4S
    N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-1-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methanesulfonamide
    —— (2S)-2-[(2-methoxy-5-methylphenyl)methylsulfonylmethyl]-2,3-dihydro-1-benzofuran —— C18H20O4S
    (2S)-2-[(2-methoxy-5-methylphenyl)methylsulfonylmethyl]-2,3-dihydro-1-benzofuran
    —— (2R)-2-[(2-methoxy-5-methylphenyl)methylsulfonylmethyl]-2,3-dihydro-1-benzofuran —— C18H20O4S
    (2R)-2-[(2-methoxy-5-methylphenyl)methylsulfonylmethyl]-2,3-dihydro-1-benzofuran
    —— N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-4-(2,5-dimethylthiophen-3-yl)-4-oxobutanamide —— C18H19NO3S
    N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-4-(2,5-dimethylthiophen-3-yl)-4-oxobutanamide
    —— 1-cyclopropyl-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-2,5-dimethylpyrrole-3-carboxamide —— C18H20N2O2
    1-cyclopropyl-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-2,5-dimethylpyrrole-3-carboxamide
    —— N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-4-methyl-2-pyrimidin-2-yl-1,3-thiazole-5-carboxamide —— C17H14N4O2S
    N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-4-methyl-2-pyrimidin-2-yl-1,3-thiazole-5-carboxamide
    —— 2-[(4-chlorophenoxy)methyl]-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-4-methyl-1,3-thiazole-5-carboxamide —— C20H17ClN2O3S
    2-[(4-chlorophenoxy)methyl]-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-4-methyl-1,3-thiazole-5-carboxamide
    —— N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-5-methyl-4-pyrrolidin-1-ylsulfonylfuran-2-carboxamide —— C18H20N2O5S
    N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-5-methyl-4-pyrrolidin-1-ylsulfonylfuran-2-carboxamide
    —— (2S)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-2-imidazol-1-ylpropanamide —— C21H21N3O2
    (2S)-N-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-2-imidazol-1-ylpropanamide
    —— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-(1-methylsulfonylpiperidin-4-yl)urea —— C15H21N3O4S
    1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-(1-methylsulfonylpiperidin-4-yl)urea
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-imidazol-1-ylpropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione —— C25H24N4O4
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-imidazol-1-ylpropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— 6-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C19H21NO4S2
    6-[(5Z)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
    —— (E)-3-(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile —— C21H24N4O2
    (E)-3-(5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile
    —— 4-[(2Z)-5-nitro-2-(2-phenoxyethylidene)-3H-1-benzofuran-3-yl]morpholine —— C20H20N2O5
    4-[(2Z)-5-nitro-2-(2-phenoxyethylidene)-3H-1-benzofuran-3-yl]morpholine
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione —— C25H21N3O4
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-4-ylmethyl)pyrrolidine-2,3-dione
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-4-ylmethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C24H20N2O4S
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-4-ylmethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— ethyl 2-[(3E)-2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C25H22N2O7S
    ethyl 2-[(3E)-2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— methyl 2-[(3E)-2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C24H20N2O7S
    methyl 2-[(3E)-2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
    —— 1-[2-(diethylamino)ethyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(pyridin-4-yl)-1,5-dihydro-2H-pyrrol-2-one —— C25H29N3O4
    1-[2-(diethylamino)ethyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(pyridin-4-yl)-1,5-dihydro-2H-pyrrol-2-one
    —— (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-morpholin-4-ylethyl)pyrrolidine-2,3-dione —— C24H26N2O6
    (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-morpholin-4-ylethyl)pyrrolidine-2,3-dione
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-pyridin-2-yl-5-thiophen-2-ylpyrrolidine-2,3-dione —— C23H18N2O4S
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-pyridin-2-yl-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 1-benzyl-3-hydroxy-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-5-(pyridin-4-yl)-2,5-dihydro-1H-pyrrol-2-one —— C26H22N2O4
    1-benzyl-3-hydroxy-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-5-(pyridin-4-yl)-2,5-dihydro-1H-pyrrol-2-one
    —— 1-[3-(dimethylamino)propyl]-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 —— C24H28N2O5
    1-[3-(dimethylamino)propyl]-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
    —— (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-imidazol-1-ylpropyl)pyrrolidine-2,3-dione —— C24H23N3O5
    (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-imidazol-1-ylpropyl)pyrrolidine-2,3-dione
    —— Carbamic acid, N-(2-methylphenyl)-, 1-(2,3-dihydro-5-benzofuryl)ethylidenamino ester —— C18H18N2O3
    Carbamic acid, N-(2-methylphenyl)-, 1-(2,3-dihydro-5-benzofuryl)ethylidenamino ester
    —— 3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methylfuran-2-yl)-1-(pyridin-3-ylmethyl)-1,5-dihydro-2H-pyrrol-2-one —— C25H22N2O5
    3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methylfuran-2-yl)-1-(pyridin-3-ylmethyl)-1,5-dihydro-2H-pyrrol-2-one
    —— 4-{(2Z)-5-chloro-2-[2-(2,4-dichlorophenoxy)ethylidene]-2,3-dihydro-1-benzofuran-3-yl}morpholine —— C20H18Cl3NO3
    4-{(2Z)-5-chloro-2-[2-(2,4-dichlorophenoxy)ethylidene]-2,3-dihydro-1-benzofuran-3-yl}morpholine
    —— [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(4-methylphenyl)carbamate —— C18H18N2O3
    [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(4-methylphenyl)carbamate
    —— (4E,5R)-1-[2-(diethylamino)ethyl]-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione —— C24H28N2O5
    (4E,5R)-1-[2-(diethylamino)ethyl]-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione