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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
    —— (1S,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylcyclopropane-1-carboxamide —— C17H23NO3
    (1S,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylcyclopropane-1-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(5-methylthiophen-2-yl)-4-oxobutanamide —— C21H25NO4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(5-methylthiophen-2-yl)-4-oxobutanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,5-dimethylthiophene-3-carboxamide —— C19H23NO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,5-dimethylthiophene-3-carboxamide
    —— (5S,7R)-3-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]adamantane-1-carboxamide —— C23H30BrNO3
    (5S,7R)-3-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]adamantane-1-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylpropanamide —— C16H23NO3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylpropanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-thiophen-2-ylpropanamide —— C19H23NO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-thiophen-2-ylpropanamide
    —— 2-cyclopentyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C19H27NO3
    2-cyclopentyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-thiophen-3-ylpropanamide —— C19H23NO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-thiophen-3-ylpropanamide
    —— 2-[2-(1,3-dithiolan-2-yl)phenoxy]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C23H27NO4S2
    2-[2-(1,3-dithiolan-2-yl)phenoxy]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-oxo-1-propylpyridazine-3-carboxamide —— C20H25N3O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-oxo-1-propylpyridazine-3-carboxamide
    —— (3S)-1-[(2-chlorophenyl)methyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-oxopyrrolidine-3-carboxamide —— C24H27ClN2O4
    (3S)-1-[(2-chlorophenyl)methyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-oxopyrrolidine-3-carboxamide
    —— (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide —— C21H24FNO4
    (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide
    —— (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide —— C22H27NO4
    (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide
    —— (2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide —— C21H24FNO4
    (2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(5-methylthiophen-2-yl)-4-oxobutanamide —— C21H25NO4S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(5-methylthiophen-2-yl)-4-oxobutanamide
    —— (3R)-1-[(2-chlorophenyl)methyl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-oxopyrrolidine-3-carboxamide —— C24H27ClN2O4
    (3R)-1-[(2-chlorophenyl)methyl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-oxopyrrolidine-3-carboxamide
    —— (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide —— C22H27NO4
    (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,5-dimethylthiophene-3-carboxamide —— C19H23NO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,5-dimethylthiophene-3-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1,4-dioxine-5-carboxamide —— C17H21NO5
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1,4-dioxine-5-carboxamide
    —— (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide —— C21H24FNO4
    (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)propanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(4-fluorophenyl)methylsulfanyl]acetamide —— C21H24FNO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(4-fluorophenyl)methylsulfanyl]acetamide
    —— 2-(6-chloro-3,4-dihydro-2H-1,5-benzodioxepin-8-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C23H26ClNO5
    2-(6-chloro-3,4-dihydro-2H-1,5-benzodioxepin-8-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(4-fluorophenyl)methylsulfanyl]acetamide —— C21H24FNO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(4-fluorophenyl)methylsulfanyl]acetamide
    —— 2-cyclopentyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C19H27NO3
    2-cyclopentyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— (2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide —— C22H27NO4
    (2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1,4-dioxine-5-carboxamide —— C17H21NO5
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1,4-dioxine-5-carboxamide
    —— (1R,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylcyclopropane-1-carboxamide —— C17H23NO3
    (1R,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylcyclopropane-1-carboxamide
    —— (3R)-1-[(2-chlorophenyl)methyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-oxopyrrolidine-3-carboxamide —— C24H27ClN2O4
    (3R)-1-[(2-chlorophenyl)methyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-oxopyrrolidine-3-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-methoxyphenyl)propanamide —— C22H27NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-methoxyphenyl)propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-methoxyphenyl)propanamide —— C22H27NO4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-methoxyphenyl)propanamide
    —— (2S,3S)-2,3-dimethyl-N-propyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C14H19NO2
    (2S,3S)-2,3-dimethyl-N-propyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— 3-[butanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C22H30N2O6
    3-[butanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(4-methylphenyl)methyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H32N2O7
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(4-methylphenyl)methyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-cyclopentylacetyl)-(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H32N2O6
    3-[(2-cyclopentylacetyl)-(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclobutanecarbonyl(cycloheptyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O5
    3-[cyclobutanecarbonyl(cycloheptyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-(4-acetyl-5-methylfuran-2-yl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide —— C21H25NO5
    3-(4-acetyl-5-methylfuran-2-yl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide
    —— (2R,3R)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C22H25NO4
    (2R,3R)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— 3-(4-acetyl-5-methylfuran-2-yl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide —— C21H25NO5
    3-(4-acetyl-5-methylfuran-2-yl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide
    —— 3-[(2-fluorophenyl)methyl-pent-2-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H31FN2O7
    3-[(2-fluorophenyl)methyl-pent-2-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-morpholin-4-ylethyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H33N3O6
    4-hydroxy-N-(2-hydroxyethyl)-3-[2-morpholin-4-ylethyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-fluorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H31FN2O7
    3-[(2-fluorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[butanoyl-[(4-chlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H33ClN2O7
    3-[butanoyl-[(4-chlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(4-fluorophenyl)methyl-(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H35FN2O8
    3-[(4-fluorophenyl)methyl-(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2R,3R)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H22N2O2S
    (2R,3R)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3S)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H27NO2
    (2S,3S)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3S)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H22N2O2S
    (2S,3S)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3R)-2,3-dimethyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C14H15N3O2S
    (2R,3R)-2,3-dimethyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H27NO2
    (2S,3R)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-N-benzyl-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C26H30N4O4
    (2R,3S)-N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-N-benzyl-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H27NO2
    (2R,3S)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide