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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
    —— 2-(3,5-dimethylphenoxy)-N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C22H26N2O4
    2-(3,5-dimethylphenoxy)-N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(2-methoxyphenoxy)acetamide —— C21H24N2O5
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(2-methoxyphenoxy)acetamide
    —— 2-(3,4-dimethylphenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C22H26N2O4
    2-(3,4-dimethylphenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— (E)-3-[2-[(E)-2-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]ethenyl]-1,3-thiazol-5-yl]prop-2-enoic acid —— C18H17NO4S
    (E)-3-[2-[(E)-2-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]ethenyl]-1,3-thiazol-5-yl]prop-2-enoic acid
    —— (2S)-N-[1-(2-amino-2-oxoethyl)pyrazol-3-yl]-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18N4O3
    (2S)-N-[1-(2-amino-2-oxoethyl)pyrazol-3-yl]-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 4-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1,2,4-triazolidine-3,5-dithione —— C14H16N4O2S2
    4-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1,2,4-triazolidine-3,5-dithione
    —— (2S)-5-chloro-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H20ClNO3
    (2S)-5-chloro-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S,3R)-N-[(1-benzyl-3,5-dimethylpyrazol-4-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C24H27N3O2
    (2S,3R)-N-[(1-benzyl-3,5-dimethylpyrazol-4-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R)-5-chloro-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H20ClNO3
    (2R)-5-chloro-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R,3S)-N-[(1-benzyl-3,5-dimethylpyrazol-4-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C24H27N3O2
    (2R,3S)-N-[(1-benzyl-3,5-dimethylpyrazol-4-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— N-[(1-benzylpyrazol-4-yl)methyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methylacetamide —— C24H27N3O3
    N-[(1-benzylpyrazol-4-yl)methyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methylacetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(1-oxidopyridin-1-ium-2-yl)sulfanylacetamide —— C19H22N2O4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(1-oxidopyridin-1-ium-2-yl)sulfanylacetamide
    —— (2R)-N-(1-cyanocyclohexyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propanamide —— C20H26N2O3
    (2R)-N-(1-cyanocyclohexyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propanamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methyl-N-(1-methylpiperidin-1-ium-4-yl)acetamide —— C19H29N2O3+
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methyl-N-(1-methylpiperidin-1-ium-4-yl)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1S)-1-(2-methoxy-5-methylphenyl)ethyl]acetamide —— C22H27NO4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1S)-1-(2-methoxy-5-methylphenyl)ethyl]acetamide
    —— 1-(cyclopropylmethyl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]piperidine-4-carboxamide —— C21H30N2O3
    1-(cyclopropylmethyl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]piperidine-4-carboxamide
    —— 1-(cyclopropylmethyl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]piperidine-4-carboxamide —— C21H30N2O3
    1-(cyclopropylmethyl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]piperidine-4-carboxamide
    —— 4-bromo-N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-1H-pyrrole-2-carbohydrazide —— C17H18BrN3O4
    4-bromo-N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-1H-pyrrole-2-carbohydrazide
    —— (2S)-5-fluoro-N-[2-methyl-2-[(2S)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H24FNO3
    (2S)-5-fluoro-N-[2-methyl-2-[(2S)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-fluoro-N-[2-methyl-2-[(2S)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H24FNO3
    (2R)-5-fluoro-N-[2-methyl-2-[(2S)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-fluoro-N-[2-methyl-2-[(2R)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H24FNO3
    (2S)-5-fluoro-N-[2-methyl-2-[(2R)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-fluoro-N-[2-methyl-2-[(2R)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H24FNO3
    (2R)-5-fluoro-N-[2-methyl-2-[(2R)-oxan-2-yl]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C20H24N2O3S
    (5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
    —— (5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one —— C20H24N2O3S
    (5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one
    —— (Z)-N-[3-(3,5-dimethylpyrazol-1-yl)-1,2,4-triazol-4-yl]-1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methanimine —— C19H22N6O2
    (Z)-N-[3-(3,5-dimethylpyrazol-1-yl)-1,2,4-triazol-4-yl]-1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methanimine
    —— [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3S)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone —— C21H25NO4S
    [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3S)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone
    —— [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3S)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone —— C21H25NO4S
    [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3S)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone
    —— (2S)-2-[(2S)-1-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one —— C19H22FNO3
    (2S)-2-[(2S)-1-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one
    —— [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3R)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone —— C21H25NO4S
    [(2R)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3R)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone
    —— (2S)-2-[(2R)-1-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one —— C19H22FNO3
    (2S)-2-[(2R)-1-[(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one
    —— [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3R)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone —— C21H25NO4S
    [(2S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-2-yl]-[(3R)-3-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]morpholin-4-yl]methanone
    —— (2S)-2-[(2S)-1-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one —— C19H22FNO3
    (2S)-2-[(2S)-1-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one
    —— (2S)-2-[(2R)-1-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one —— C19H22FNO3
    (2S)-2-[(2R)-1-[(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-carbonyl]pyrrolidin-2-yl]cyclohexan-1-one
    —— N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]cyclopropanecarboxamide —— C16H20N2O3
    N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]cyclopropanecarboxamide
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]cyclopropanecarboxamide —— C16H20N2O3
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]cyclopropanecarboxamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[4-(pyridin-4-ylmethyl)piperazin-4-ium-1-yl]ethanone —— C22H28N3O3+
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[4-(pyridin-4-ylmethyl)piperazin-4-ium-1-yl]ethanone
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[4-(pyridin-4-ylmethyl)piperazin-1-yl]ethanone —— C22H27N3O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[4-(pyridin-4-ylmethyl)piperazin-1-yl]ethanone
    —— (3S)-5-chloro-2,3-dihydro-1-benzofuran-3-ol —— C8H7ClO2
    (3S)-5-chloro-2,3-dihydro-1-benzofuran-3-ol
    —— (3R)-5-chloro-2,3-dihydro-1-benzofuran-3-ol —— C8H7ClO2
    (3R)-5-chloro-2,3-dihydro-1-benzofuran-3-ol
    —— (1R,2S)-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide —— C20H26N2O3
    (1R,2S)-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide
    —— (1S,2S)-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide —— C20H26N2O3
    (1S,2S)-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide
    —— (1S,2S)-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide —— C20H26N2O3
    (1S,2S)-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide
    —— (3R)-N-[(1S)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H28N2O3
    (3R)-N-[(1S)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(1S)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H28N2O3
    (3S)-N-[(1S)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(1R)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H28N2O3
    (3R)-N-[(1R)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (1R,2S)-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide —— C20H26N2O3
    (1R,2S)-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-2-(pyrrolidine-1-carbonyl)cyclohexane-1-carboxamide
    —— (3S)-N-[(1R)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C20H28N2O3
    (3S)-N-[(1R)-1-(1-morpholin-4-ylcyclopentyl)ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-(3,5-dimethyl-1,2-oxazol-4-yl)-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H16N2O3
    (3R)-N-(3,5-dimethyl-1,2-oxazol-4-yl)-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-(3,5-dimethyl-1,2-oxazol-4-yl)-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H16N2O3
    (3S)-N-(3,5-dimethyl-1,2-oxazol-4-yl)-N-methyl-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (E)-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)prop-2-enenitrile —— C20H17N3O3S
    (E)-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)prop-2-enenitrile