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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-[(1R)-1-phenylethyl]-N-(pyridin-2-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide —— C23H22N2O2
    N-[(1R)-1-phenylethyl]-N-(pyridin-2-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide
    —— ethyl (1S,2S)-2-[[cyclohexyl(2,3-dihydro-1-benzofuran-5-carbonyl)amino]methyl]cyclopropane-1-carboxylate —— C22H29NO4
    ethyl (1S,2S)-2-[[cyclohexyl(2,3-dihydro-1-benzofuran-5-carbonyl)amino]methyl]cyclopropane-1-carboxylate
    —— ethyl (1R,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate —— C25H29NO4
    ethyl (1R,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate
    —— N-benzyl-N-(1,3-thiazol-2-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide —— C20H18N2O2S
    N-benzyl-N-(1,3-thiazol-2-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-(furan-3-ylmethyl)-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C22H21NO3
    N-(furan-3-ylmethyl)-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— ethyl (1R,2R)-2-[[butyl(2,3-dihydro-1-benzofuran-7-carbonyl)amino]methyl]cyclopropane-1-carboxylate —— C20H27NO4
    ethyl (1R,2R)-2-[[butyl(2,3-dihydro-1-benzofuran-7-carbonyl)amino]methyl]cyclopropane-1-carboxylate
    —— N-(furan-2-ylmethyl)-N-[(2R)-4-phenylbutan-2-yl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C24H25NO3
    N-(furan-2-ylmethyl)-N-[(2R)-4-phenylbutan-2-yl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R)-2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl chloride —— C10H9ClO2
    (2R)-2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl chloride
    —— N-[(1-methylimidazol-2-yl)methyl]-N-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C23H25N3O2
    N-[(1-methylimidazol-2-yl)methyl]-N-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— N-(2-methylpropyl)-N-(pyridin-4-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide —— C19H22N2O2
    N-(2-methylpropyl)-N-(pyridin-4-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide
    —— [(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylazanium —— C10H14NO+
    [(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylazanium
    —— N-[(2-methylphenyl)methyl]-N-[(2R)-4-phenylbutan-2-yl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C27H29NO2
    N-[(2-methylphenyl)methyl]-N-[(2R)-4-phenylbutan-2-yl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— [(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine —— C10H13NO
    [(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine
    —— N-[(1S)-1-phenylethyl]-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C23H22N2O2
    N-[(1S)-1-phenylethyl]-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (4E,5S)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione —— C23H25NO6
    (4E,5S)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(4-pyridin-3-yl-1,3-thiazol-2-yl)acetamide —— C20H19N3O3S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(4-pyridin-3-yl-1,3-thiazol-2-yl)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[4-(2,4,5-trimethylphenyl)-1,3-thiazol-2-yl]acetamide —— C24H26N2O3S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[4-(2,4,5-trimethylphenyl)-1,3-thiazol-2-yl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[4-(3,4-dimethylphenyl)-1,3-thiazol-2-yl]acetamide —— C23H24N2O3S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[4-(3,4-dimethylphenyl)-1,3-thiazol-2-yl]acetamide
    —— 2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]propanedinitrile —— C15H14N2O2
    2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]propanedinitrile
    —— 2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]propanedinitrile —— C15H14N2O2
    2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]propanedinitrile
    —— (4E,5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-imidazol-1-ylpropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C24H23N3O4S
    (4E,5S)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-imidazol-1-ylpropyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— (4E,5S)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-imidazol-1-ylpropyl)pyrrolidine-2,3-dione —— C24H23N3O5
    (4E,5S)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-imidazol-1-ylpropyl)pyrrolidine-2,3-dione
    —— (4E,5R)-1-benzyl-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-5-pyridin-4-ylpyrrolidine-2,3-dione —— C26H22N2O4
    (4E,5R)-1-benzyl-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— (4E,5R)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione —— C25H21NO5
    (4E,5R)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione
    —— 6-[[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methylidene]-4-nitrocyclohexa-2,4-dien-1-one —— C19H20N2O5
    6-[[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methylidene]-4-nitrocyclohexa-2,4-dien-1-one
    —— 6-[[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methylidene]-2-methoxycyclohexa-2,4-dien-1-one —— C20H23NO4
    6-[[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]methylidene]-2-methoxycyclohexa-2,4-dien-1-one
    —— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-phenethylacetamide —— C20H23NO3
    2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-phenethylacetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(furan-2-ylmethyl)acetamide —— C17H19NO4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(furan-2-ylmethyl)acetamide
    —— (5R)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione —— C23H25NO6
    (5R)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-(3-methoxypropyl)-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione
    —— (5S)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione —— C25H21NO5
    (5S)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione
    —— (5R)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione —— C25H21NO5
    (5R)-1-benzyl-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrrolidine-2,3-dione
    —— (5E)-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H19NO3S2
    (5E)-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— 4-(4-tert-butylphenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]butanamide —— C26H35NO4
    4-(4-tert-butylphenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]butanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-methoxyphenyl)propanamide —— C22H27NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-methoxyphenyl)propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(2-ethoxyphenoxy)butanamide —— C24H31NO5
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(2-ethoxyphenoxy)butanamide
    —— 2-(2-chlorophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H22ClNO4
    2-(2-chlorophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— [(2R)-1-[2-(dimethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate —— C23H26N2O5
    [(2R)-1-[2-(dimethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate
    —— (5E)-3-[(3R)-1,1-dioxothiolan-3-yl]-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H17NO4S3
    (5E)-3-[(3R)-1,1-dioxothiolan-3-yl]-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— 3-[(2R)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]propyl-dimethylazanium —— C24H29N2O5+
    3-[(2R)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]propyl-dimethylazanium
    —— 3-[(2S)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]propyl-dimethylazanium —— C24H29N2O5+
    3-[(2S)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]propyl-dimethylazanium
    —— (5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H19NO3S2
    (5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H19NO3S2
    (5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-prop-2-enyl-2-sulfanylidene-1,3-thiazolidin-4-one
    —— 6-[(E)-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-5-nitro-1H-pyrimidine-2,4-dione —— C15H13N3O5
    6-[(E)-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-5-nitro-1H-pyrimidine-2,4-dione
    —— (S)-2-Methyl-2,3-dihydrobenzofuran-5-carbaldehyde —— C10H10O2
    (S)-2-Methyl-2,3-dihydrobenzofuran-5-carbaldehyde
    —— 3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propanoate —— C12H13O3-
    3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propanoate
    —— (2R)-2-methyl-2,3-dihydro-1-benzofuran-5-carbaldehyde —— C10H10O2
    (2R)-2-methyl-2,3-dihydro-1-benzofuran-5-carbaldehyde
    —— (2S)-2-methyl-5-[(E)-2-nitroethenyl]-2,3-dihydro-1-benzofuran —— C11H11NO3
    (2S)-2-methyl-5-[(E)-2-nitroethenyl]-2,3-dihydro-1-benzofuran
    —— (2Z,3S)-2-[(3-bromo-5-chloro-2-methoxyphenyl)methylidene]-3H-1-benzofuran-3-ol —— C16H12BrClO3
    (2Z,3S)-2-[(3-bromo-5-chloro-2-methoxyphenyl)methylidene]-3H-1-benzofuran-3-ol
    —— (1E,2R)-2-methyl-1-[(3R)-3-piperidin-1-ium-1-yl-3H-1-benzofuran-2-ylidene]butan-2-ol —— C18H26NO2+
    (1E,2R)-2-methyl-1-[(3R)-3-piperidin-1-ium-1-yl-3H-1-benzofuran-2-ylidene]butan-2-ol
    —— (1E,2S)-2-methyl-1-[(3R)-3-piperidin-1-ium-1-yl-3H-1-benzofuran-2-ylidene]butan-2-ol —— C18H26NO2+
    (1E,2S)-2-methyl-1-[(3R)-3-piperidin-1-ium-1-yl-3H-1-benzofuran-2-ylidene]butan-2-ol