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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-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylamino]propanenitrile —— C12H14N2O
    (2S)-2-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylamino]propanenitrile
    —— (2R)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-amine —— C13H19NO2
    (2R)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-amine
    —— 3-[cyclohexyl(cyclopentanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H38N2O7
    3-[cyclohexyl(cyclopentanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentanecarbonyl(3-ethoxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O6
    3-[cyclopentanecarbonyl(3-ethoxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2S)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-amine —— C13H19NO2
    (2S)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-amine
    —— 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-[(2,3,4-trifluorophenyl)methyl]-1,3-thiazolidin-4-one —— C18H14F3NO2S
    2-(2,3-Dihydro-1-benzofuran-5-yl)-3-[(2,3,4-trifluorophenyl)methyl]-1,3-thiazolidin-4-one
    —— 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-[(3-methoxyphenyl)methyl]-1,3-thiazinan-4-one —— C20H21NO3S
    2-(2,3-Dihydro-1-benzofuran-5-yl)-3-[(3-methoxyphenyl)methyl]-1,3-thiazinan-4-one
    —— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[oxolane-2-carbonyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O9
    4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[oxolane-2-carbonyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2,5-dimethylpyrazol-3-yl)urea —— C15H18N4O2
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2,5-dimethylpyrazol-3-yl)urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2,5-dimethylpyrazol-3-yl)urea —— C15H18N4O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2,5-dimethylpyrazol-3-yl)urea
    —— N-[2-(2-chlorophenoxy)ethyl]-2-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]acetamide —— C20H22ClNO4
    N-[2-(2-chlorophenoxy)ethyl]-2-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]acetamide
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2-imidazol-1-ylethyl)urea —— C15H18N4O2
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2-imidazol-1-ylethyl)urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2-imidazol-1-ylethyl)urea —— C15H18N4O2
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2-imidazol-1-ylethyl)urea
    —— 5-[(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-3-(2-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C21H19NO2S2
    5-[(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-3-(2-phenylethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (3R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-pyrimidin-2-ylpiperidin-3-amine —— C18H22N4O
    (3R)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-pyrimidin-2-ylpiperidin-3-amine
    —— N-[(2-fluorophenyl)methyl]-3-imidazol-1-yl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-1-amine —— C23H26FN3O
    N-[(2-fluorophenyl)methyl]-3-imidazol-1-yl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-1-amine
    —— (3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-pyrimidin-2-ylpiperidin-3-amine —— C18H22N4O
    (3S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-pyrimidin-2-ylpiperidin-3-amine
    —— 3-imidazol-1-yl-N-[(2-methoxyphenyl)methyl]-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-1-amine —— C24H29N3O2
    3-imidazol-1-yl-N-[(2-methoxyphenyl)methyl]-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-1-amine
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(4-methyl-1,3-thiazol-2-yl)urea —— C14H15N3O2S
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(4-methyl-1,3-thiazol-2-yl)urea
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(4-methyl-1,3-thiazol-2-yl)urea —— C14H15N3O2S
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(4-methyl-1,3-thiazol-2-yl)urea
    —— (2R)-5-chloro-N-[(4-cyanophenyl)methyl]-N-(2,2,2-trifluoroethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H14ClF3N2O2
    (2R)-5-chloro-N-[(4-cyanophenyl)methyl]-N-(2,2,2-trifluoroethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-[(5-Ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]propanedinitrile —— C15H14N2O2
    2-[(5-Ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)methylidene]propanedinitrile
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1,3-thiazol-2-yl)urea —— C13H13N3O2S
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1,3-thiazol-2-yl)urea
    —— 3-[dodecanoyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C32H44N2O6
    3-[dodecanoyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[dodecanoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C38H54N2O8
    3-[dodecanoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopropanecarbonyl(oxolan-2-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H30N2O6
    3-[cyclopropanecarbonyl(oxolan-2-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (E)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-pyridin-2-ylprop-2-enenitrile —— C19H18N2O2
    (E)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-pyridin-2-ylprop-2-enenitrile
    —— 3-[1-adamantylmethyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H42N2O7
    3-[1-adamantylmethyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-ethoxyacetyl)-(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H40N2O9
    3-[(2-ethoxyacetyl)-(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H44N2O7
    3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[butanoyl(oxolan-2-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H32N2O6
    3-[butanoyl(oxolan-2-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 2-(2,3-Dihydro-1-benzofuran-5-yl)benzoic acid —— C15H12O3
    2-(2,3-Dihydro-1-benzofuran-5-yl)benzoic acid
    —— 3-[1-adamantylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H46N2O8
    3-[1-adamantylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O7
    3-[cyclopentyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(4-chlorophenyl)methyl-(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H31ClN2O5
    3-[(4-chlorophenyl)methyl-(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopropylmethyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H42N2O7
    3-[cyclopropylmethyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-cyclopentylacetyl)-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H38N2O6
    3-[(2-cyclopentylacetyl)-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-ethoxypropyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O6
    3-[3-ethoxypropyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-cyclopentylacetyl)-(cyclopropylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H36N2O7
    3-[(2-cyclopentylacetyl)-(cyclopropylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[1-adamantylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H46N2O7
    3-[1-adamantylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-[3-(1H-imidazol-3-ium-3-yl)propyl]-5-thiophen-2-ylpyrrolidine-2,3-dione —— C24H24N3O4S+
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-[3-(1H-imidazol-3-ium-3-yl)propyl]-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— (2S)-5-ethoxy-2-methyl-6-[(Z)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran —— C14H17NO4
    (2S)-5-ethoxy-2-methyl-6-[(Z)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran
    —— (2R)-5-ethoxy-2-methyl-6-[(Z)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran —— C14H17NO4
    (2R)-5-ethoxy-2-methyl-6-[(Z)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran
    —— (2R)-5-ethoxy-2-methyl-6-[(E)-2-nitroethenyl]-2,3-dihydro-1-benzofuran —— C13H15NO4
    (2R)-5-ethoxy-2-methyl-6-[(E)-2-nitroethenyl]-2,3-dihydro-1-benzofuran
    —— (2S)-5-ethoxy-2-methyl-6-[(E)-2-nitroethenyl]-2,3-dihydro-1-benzofuran —— C13H15NO4
    (2S)-5-ethoxy-2-methyl-6-[(E)-2-nitroethenyl]-2,3-dihydro-1-benzofuran
    —— 1-(1-adamantyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-one —— C23H30O3
    1-(1-adamantyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-one
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1S,2R)-2-methylcyclohexyl]methanamine —— C17H25NO
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1S,2R)-2-methylcyclohexyl]methanamine
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1S,2S)-2-methylcyclohexyl]methanamine —— C17H25NO
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1S,2S)-2-methylcyclohexyl]methanamine
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1R,2S)-2-methylcyclohexyl]methanamine —— C17H25NO
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1R,2S)-2-methylcyclohexyl]methanamine
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1R,2R)-2-methylcyclohexyl]methanamine —— C17H25NO
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(1R,2R)-2-methylcyclohexyl]methanamine