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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
    —— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methoxypropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H40N2O9
    4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methoxypropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentanecarbonyl(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H42N2O8
    3-[cyclopentanecarbonyl(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[2-(3-fluorophenyl)ethyl-(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H33FN2O7
    3-[2-(3-fluorophenyl)ethyl-(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[acetyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H31FN2O7
    3-[acetyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H34N2O9
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentanecarbonyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O5
    3-[cyclopentanecarbonyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclobutanecarbonyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H38N2O8
    3-[cyclobutanecarbonyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-ethoxypropyl(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H40N2O8
    3-[3-ethoxypropyl(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— [(2R)-7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H14N2O
    [(2R)-7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— (2S)-2-ethyl-3H-1-benzofuran-2-carbonitrile —— C11H11NO
    (2S)-2-ethyl-3H-1-benzofuran-2-carbonitrile
    —— [(2R)-7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H16ClNO
    [(2R)-7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— [(2S)-7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H16ClNO
    [(2S)-7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— (3aR,8bR)-8b-methoxy-1,3a-dihydrofuro[2,3-b][1]benzofuran-2-one —— C11H10O4
    (3aR,8bR)-8b-methoxy-1,3a-dihydrofuro[2,3-b][1]benzofuran-2-one
    —— (3aS,8bR)-8b-methoxy-1,3a-dihydrofuro[2,3-b][1]benzofuran-2-one —— C11H10O4
    (3aS,8bR)-8b-methoxy-1,3a-dihydrofuro[2,3-b][1]benzofuran-2-one
    —— (3S)-3-methyl-2,3-dihydro-1-benzofuran-6-ol —— C9H10O2
    (3S)-3-methyl-2,3-dihydro-1-benzofuran-6-ol
    —— 2-[(2S,3S)-2-ethenyl-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C12H12O3
    2-[(2S,3S)-2-ethenyl-2,3-dihydro-1-benzofuran-3-yl]acetic acid
    —— 2-[(2R,3R)-2-ethenyl-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C12H12O3
    2-[(2R,3R)-2-ethenyl-2,3-dihydro-1-benzofuran-3-yl]acetic acid
    —— 3-[1-adamantylmethyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H46N2O7
    3-[1-adamantylmethyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[3-methylbutanoyl(2-morpholin-4-ylethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H37N3O6
    4-hydroxy-N-(2-hydroxyethyl)-3-[3-methylbutanoyl(2-morpholin-4-ylethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3S)-2,2-dimethyl-3-piperidin-1-yl-3H-1-benzofuran-7-ol —— C15H21NO2
    (3S)-2,2-dimethyl-3-piperidin-1-yl-3H-1-benzofuran-7-ol
    —— 3-[cyclohexylmethyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H38N2O5
    3-[cyclohexylmethyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol —— C10H12O2
    (2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol
    —— (2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol —— C10H12O2
    (2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol
    —— (2S)-5-ethylsulfonyl-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylic acid —— C12H14O5S
    (2S)-5-ethylsulfonyl-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylic acid
    —— (2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol —— C10H12O2
    (2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol
    —— (2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol —— C10H12O2
    (2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-6-ol
    —— (2S)-6,7-dimethyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid —— C11H13NO5S
    (2S)-6,7-dimethyl-5-sulfamoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid
    —— 3-[1-adamantylmethyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H38N2O6
    3-[1-adamantylmethyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2,4-dichlorophenyl)methyl-(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H30Cl2N2O5
    3-[(2,4-dichlorophenyl)methyl-(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2R)-2-methyl-5-(methylsulfamoyl)-2,3-dihydro-1-benzofuran-7-carboxylic acid —— C11H13NO5S
    (2R)-2-methyl-5-(methylsulfamoyl)-2,3-dihydro-1-benzofuran-7-carboxylic acid
    —— 3-[benzyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H36N2O8
    3-[benzyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[hept-6-enoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H38N2O8
    3-[hept-6-enoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methoxypropanoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O9
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methoxypropanoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-fluorophenyl)methyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H29FN2O8
    3-[(2-fluorophenyl)methyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[1-adamantylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C32H42N2O6
    3-[1-adamantylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-pent-2-enoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H34N2O6
    4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-pent-2-enoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2R)-7-chloro-6-hydroxy-5-propanoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid —— C12H11ClO5
    (2R)-7-chloro-6-hydroxy-5-propanoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid
    —— ethyl (3S)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylate —— C11H11BrO3
    ethyl (3S)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylate
    —— ethyl (3R)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylate —— C11H11BrO3
    ethyl (3R)-5-bromo-2,3-dihydro-1-benzofuran-3-carboxylate
    —— (2S)-7-chloro-6-hydroxy-5-propanoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid —— C12H11ClO5
    (2S)-7-chloro-6-hydroxy-5-propanoyl-2,3-dihydro-1-benzofuran-2-carboxylic acid
    —— (2S)-2,4-dimethyl-2,3-dihydro-1-benzofuran-7-amine —— C10H13NO
    (2S)-2,4-dimethyl-2,3-dihydro-1-benzofuran-7-amine
    —— [(2S)-2,4-dimethyl-2,3-dihydro-1-benzofuran-7-yl]hydrazine —— C10H14N2O
    [(2S)-2,4-dimethyl-2,3-dihydro-1-benzofuran-7-yl]hydrazine
    —— 3-[dodecanoyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H48N2O8
    3-[dodecanoyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— [(2S)-2-methyl-2,3-dihydro-1-benzofuran-7-yl]hydrazine —— C9H12N2O
    [(2S)-2-methyl-2,3-dihydro-1-benzofuran-7-yl]hydrazine
    —— (2R)-2,4-dimethyl-2,3-dihydro-1-benzofuran-7-amine —— C10H13NO
    (2R)-2,4-dimethyl-2,3-dihydro-1-benzofuran-7-amine
    —— 1-[2-(Diethylamino)ethyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione —— C25H30N2O5
    1-[2-(Diethylamino)ethyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione
    —— [1-[2-(Diethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate —— C25H30N2O5
    [1-[2-(Diethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate
    —— N-(4,5-dihydro-1,3-thiazol-2-yl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C15H18N2O3S
    N-(4,5-dihydro-1,3-thiazol-2-yl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— methyl 2-[(3R)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]acetate —— C17H14O4
    methyl 2-[(3R)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]acetate
    —— (2S)-2-[(3R)-3-(4-bromophenyl)-2-oxo-3H-1-benzofuran-5-yl]propanoic acid —— C17H13BrO4
    (2S)-2-[(3R)-3-(4-bromophenyl)-2-oxo-3H-1-benzofuran-5-yl]propanoic acid