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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,3R)-N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-N-benzyl-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C26H30N4O4
    (2S,3R)-N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-N-benzyl-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— methyl 5-[[(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]amino]thiophene-2-carboxylate —— C17H17NO4S
    methyl 5-[[(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]amino]thiophene-2-carboxylate
    —— (2R,3R)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H27NO2
    (2R,3R)-N-(2-adamantyl)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H22N2O2S
    (2S,3R)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H22N2O2S
    (2R,3S)-N-[2-[(2-cyanophenyl)methylsulfanyl]ethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— methyl 5-[[(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]amino]thiophene-2-carboxylate —— C17H17NO4S
    methyl 5-[[(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]amino]thiophene-2-carboxylate
    —— (2R,3R)-N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-N-benzyl-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C26H30N4O4
    (2R,3R)-N-(6-amino-1-butyl-2,4-dioxopyrimidin-5-yl)-N-benzyl-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-2,3-dimethyl-N-prop-2-enyl-N-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H24N2O2S
    (2S,3R)-2,3-dimethyl-N-prop-2-enyl-N-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-2,3-dimethyl-N-(pyridin-2-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C17H18N2O2
    (2S,3R)-2,3-dimethyl-N-(pyridin-2-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3R)-2,3-dimethyl-N-(pyridin-2-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C17H18N2O2
    (2R,3R)-2,3-dimethyl-N-(pyridin-2-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R,3S)-2,3-dimethyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C14H15N3O2S
    (2R,3S)-2,3-dimethyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— [(3S)-2,3-dihydro-1-benzofuran-3-yl]methanamine —— C9H11NO
    [(3S)-2,3-dihydro-1-benzofuran-3-yl]methanamine
    —— [(3R)-2,3-dihydro-1-benzofuran-3-yl]methanamine —— C9H11NO
    [(3R)-2,3-dihydro-1-benzofuran-3-yl]methanamine
    —— (3R)-3-methoxy-2,3-dihydro-1-benzofuran —— C9H10O2
    (3R)-3-methoxy-2,3-dihydro-1-benzofuran
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(2-methoxyacetyl)-[(4-methylphenyl)methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H32N2O8
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(2-methoxyacetyl)-[(4-methylphenyl)methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[furan-3-ylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H30N2O7
    3-[furan-3-ylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3S)-3-methoxy-2,3-dihydro-1-benzofuran —— C9H10O2
    (3S)-3-methoxy-2,3-dihydro-1-benzofuran
    —— 1-(2-chlorophenyl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-methyl-4-oxopyridazine-3-carboxamide —— C24H24ClN3O4
    1-(2-chlorophenyl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-methyl-4-oxopyridazine-3-carboxamide
    —— 3-[1-adamantylmethyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H44N2O7
    3-[1-adamantylmethyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentyl(hept-6-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H38N2O7
    3-[cyclopentyl(hept-6-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2R)-5-chloro-N-cyclopropyl-N-[[4-(difluoromethoxy)-3-ethoxyphenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H22ClF2NO4
    (2R)-5-chloro-N-cyclopropyl-N-[[4-(difluoromethoxy)-3-ethoxyphenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-cyclopropyl-N-[[4-(difluoromethoxy)-3-ethoxyphenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H23F2NO4
    (2R)-N-cyclopropyl-N-[[4-(difluoromethoxy)-3-ethoxyphenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-(2-adamantyl)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H22ClNO2
    (2S)-N-(2-adamantyl)-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 3-[cyclohexylmethyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O5
    3-[cyclohexylmethyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2S)-N-(2-adamantyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H23NO2
    (2S)-N-(2-adamantyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-cyclopropyl-N-[[4-(difluoromethoxy)-3-ethoxyphenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H23F2NO4
    (2S)-N-cyclopropyl-N-[[4-(difluoromethoxy)-3-ethoxyphenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(S)-phenyl(pyridin-2-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H18N2O2
    (2S)-N-[(S)-phenyl(pyridin-2-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(R)-phenyl(pyridin-2-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H18N2O2
    (2R)-N-[(R)-phenyl(pyridin-2-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(1S)-1-[4-(2-methylpropyl)phenyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H25NO2
    (2S)-N-[(1S)-1-[4-(2-methylpropyl)phenyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H13BrN2O2S
    (2R)-N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(4-pyridin-2-yl-1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H13N3O2S
    (2R)-N-(4-pyridin-2-yl-1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[4-(2,5-dimethyl-1-prop-2-enylpyrrol-3-yl)-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H21N3O2S
    (2R)-N-[4-(2,5-dimethyl-1-prop-2-enylpyrrol-3-yl)-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-(4-pyridin-2-yl-1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H13N3O2S
    (2S)-N-(4-pyridin-2-yl-1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carboxamide —— C24H28F3N3O3
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carboxamide —— C24H28F3N3O3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanamide —— C23H25N3O4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanamide
    —— 3-[benzyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H30N2O6
    3-[benzyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanamide —— C23H25N3O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanamide
    —— 3-[(2-fluorophenyl)methyl-(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H33FN2O8
    3-[(2-fluorophenyl)methyl-(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2,4-dichlorophenyl)methyl-(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H30Cl2N2O7
    3-[(2,4-dichlorophenyl)methyl-(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O8
    4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclohexylmethyl-(2-ethoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H38N2O8
    3-[cyclohexylmethyl-(2-ethoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclohexyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O8
    3-[cyclohexyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-cyclopentylpropanoyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H41N3O6
    3-[3-cyclopentylpropanoyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 1-[5-(2,3-Dihydro-1-benzofuran-5-yl)thiophen-2-yl]ethanone —— C14H12O2S
    1-[5-(2,3-Dihydro-1-benzofuran-5-yl)thiophen-2-yl]ethanone
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methylpropanoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O8
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methylpropanoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[1-adamantylmethyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C35H48N2O7
    3-[1-adamantylmethyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-(3-methoxypropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H34N2O7
    4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-(3-methoxypropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[1-adamantylmethyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H40N2O5
    3-[1-adamantylmethyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[benzyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H34N2O7
    3-[benzyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide