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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
    —— (2S)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-1-morpholin-4-ylethanone —— C14H16ClNO3
    (2S)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-1-morpholin-4-ylethanone
    —— (2R)-2-chloro-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-N-methylacetamide —— C14H18ClNO3
    (2R)-2-chloro-2-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-N-methylacetamide
    —— (2S)-5-[(S)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19BrO2
    (2S)-5-[(S)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
    —— (2R)-2-chloro-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-N-methylacetamide —— C14H18ClNO3
    (2R)-2-chloro-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-N-methylacetamide
    —— (2S)-5-[(S)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19ClO2
    (2S)-5-[(S)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
    —— (2S)-5-[(R)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19BrO2
    (2S)-5-[(R)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
    —— (2R)-5-[(R)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19ClO2
    (2R)-5-[(R)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
    —— 5-[(S)-bromo-[(2S)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran —— C14H17BrO2
    5-[(S)-bromo-[(2S)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran
    —— (2R)-5-[(S)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19ClO2
    (2R)-5-[(S)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
    —— (S)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanol —— C14H18O3
    (S)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanol
    —— (R)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanamine —— C14H19NO2
    (R)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanamine
    —— (S)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanamine —— C14H19NO2
    (S)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanamine
    —— (R)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanamine —— C14H19NO2
    (R)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanamine
    —— (S)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanol —— C14H18O3
    (S)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanol
    —— (1R)-1-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-N-methylethanamine —— C13H15N3O2
    (1R)-1-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-N-methylethanamine
    —— N-[(3S,4S)-4-methoxypyrrolidin-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C14H18N2O3
    N-[(3S,4S)-4-methoxypyrrolidin-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[(3R,4S)-4-methoxypyrrolidin-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C14H18N2O3
    N-[(3R,4S)-4-methoxypyrrolidin-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— (S)-cyclopropyl-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]methanamine —— C14H15N3O2
    (S)-cyclopropyl-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]methanamine
    —— (R)-(2,5-difluorophenyl)-(2,3-dihydro-1-benzofuran-5-yl)methanol —— C15H12F2O2
    (R)-(2,5-difluorophenyl)-(2,3-dihydro-1-benzofuran-5-yl)methanol
    —— N-[(S)-(5-chlorothiophen-2-yl)-(2,3-dihydro-1-benzofuran-5-yl)methyl]ethanamine —— C15H16ClNOS
    N-[(S)-(5-chlorothiophen-2-yl)-(2,3-dihydro-1-benzofuran-5-yl)methyl]ethanamine
    —— N-[(2S)-1-amino-1-sulfanylidenepropan-2-yl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C12H14N2O2S
    N-[(2S)-1-amino-1-sulfanylidenepropan-2-yl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— (1R)-1-(5-chlorothiophen-2-yl)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methylmethanamine —— C14H14ClNOS
    (1R)-1-(5-chlorothiophen-2-yl)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methylmethanamine
    —— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine —— C14H15NOS
    (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine
    —— (R)-(2,5-dibromothiophen-3-yl)-(2,3-dihydro-1-benzofuran-5-yl)methanol —— C13H10Br2O2S
    (R)-(2,5-dibromothiophen-3-yl)-(2,3-dihydro-1-benzofuran-5-yl)methanol
    —— N-[(1E,2S)-1-amino-1-hydroxyiminopropan-2-yl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C12H15N3O3
    N-[(1E,2S)-1-amino-1-hydroxyiminopropan-2-yl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— (3S)-3-[[(2R)-hexan-2-yl]amino]-2,3-dihydro-1-benzofuran-6-ol —— C14H21NO2
    (3S)-3-[[(2R)-hexan-2-yl]amino]-2,3-dihydro-1-benzofuran-6-ol
    —— (3R)-3-[[(2S)-hexan-2-yl]amino]-2,3-dihydro-1-benzofuran-6-ol —— C14H21NO2
    (3R)-3-[[(2S)-hexan-2-yl]amino]-2,3-dihydro-1-benzofuran-6-ol
    —— (2S)-5-chloro-N-[[3-(difluoromethoxy)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H14ClF2NO3
    (2S)-5-chloro-N-[[3-(difluoromethoxy)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (1R)-1-(cyclohepten-1-yl)-1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-methylmethanamine —— C17H23NO
    (1R)-1-(cyclohepten-1-yl)-1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-methylmethanamine
    —— N-[(S)-cyclohexen-1-yl-[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]ethanamine —— C17H23NO
    N-[(S)-cyclohexen-1-yl-[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]ethanamine
    —— [1-(furan-2-ylmethyl)piperidin-2-yl]methyl N-(2,3-dihydro-1-benzofuran-5-ylmethyl)carbamate —— C21H26N2O4
    [1-(furan-2-ylmethyl)piperidin-2-yl]methyl N-(2,3-dihydro-1-benzofuran-5-ylmethyl)carbamate
    —— (3R)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]pyrrolidine —— C15H21NO2
    (3R)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]pyrrolidine
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(2R)-3,4-dihydro-2H-pyran-2-yl]methanamine —— C15H19NO2
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(2R)-3,4-dihydro-2H-pyran-2-yl]methanamine
    —— 2-(2,4,6-trimethylphenyl)ethyl N-[[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]amino]carbamate —— C24H30N2O5
    2-(2,4,6-trimethylphenyl)ethyl N-[[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]amino]carbamate
    —— N-[(2R)-2-(dimethylamino)-2-(furan-2-yl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C20H26N2O4
    N-[(2R)-2-(dimethylamino)-2-(furan-2-yl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H36N2O8
    (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H35FN2O8
    (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[butanoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H38N2O8
    (3R,4S,4aS,9bS)-3-[butanoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[(3,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H36Cl2N2O7
    (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[(3,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(2,4-dichlorophenyl)methyl-pent-4-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H32Cl2N2O7
    (3R,4S,4aS,9bS)-3-[(2,4-dichlorophenyl)methyl-pent-4-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H30Cl2N2O8
    (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H32Cl2N2O7
    (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[dodecanoyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C38H54N2O8
    (3R,4S,4aS,9bS)-3-[dodecanoyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(3-methoxyphenyl)ethyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H36N2O8
    (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(3-methoxyphenyl)ethyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H32Cl2N2O8
    (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C32H39FN2O7
    (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H31ClN2O7
    (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H34Cl2N2O7
    (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(oxolane-2-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H38N2O9
    (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(oxolane-2-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-pent-4-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H35FN2O7
    (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-pent-4-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide