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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
    —— 2-chloro-1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone —— C11H11ClO2
    2-chloro-1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone
    —— (2S)-5-methoxy-2-methyl-6,7-dinitro-2,3-dihydro-1-benzofuran —— C10H10N2O6
    (2S)-5-methoxy-2-methyl-6,7-dinitro-2,3-dihydro-1-benzofuran
    —— N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-2-amine —— C13H19NO
    N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-2-amine
    —— N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-1-amine —— C13H19NO
    N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]propan-1-amine
    —— [(Z)-[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]thiourea —— C12H15N3O2S
    [(Z)-[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]thiourea
    —— [(Z)-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]thiourea —— C12H15N3O2S
    [(Z)-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]thiourea
    —— (2R)-2,3-dihydro-1-benzofuran-2-carboxylate —— C9H7O3-
    (2R)-2,3-dihydro-1-benzofuran-2-carboxylate
    —— (2R)-5-methoxy-2-methyl-6-[(E)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran —— C13H15NO4
    (2R)-5-methoxy-2-methyl-6-[(E)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran
    —— (2S)-5-methoxy-2-methyl-6-[(E)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran —— C13H15NO4
    (2S)-5-methoxy-2-methyl-6-[(E)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran
    —— [(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl carbamimidothioate —— C11H14N2OS
    [(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl carbamimidothioate
    —— (3aR,8bS)-3a-morpholin-4-ium-4-yl-1,2,3,8b-tetrahydrocyclopenta[b][1]benzofuran-7-ol —— C15H20NO3+
    (3aR,8bS)-3a-morpholin-4-ium-4-yl-1,2,3,8b-tetrahydrocyclopenta[b][1]benzofuran-7-ol
    —— 1-[(3R)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]piperidine —— C16H22N2O3
    1-[(3R)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]piperidine
    —— (2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate —— C11H11O3-
    (2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate
    —— 1-[(3R)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]piperidin-1-ium —— C16H23N2O3+
    1-[(3R)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]piperidin-1-ium
    —— 1-[(3S)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]piperidin-1-ium —— C16H23N2O3+
    1-[(3S)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]piperidin-1-ium
    —— (2R,6R)-2,6-dimethyl-4-[(3S)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]morpholine —— C17H24N2O4
    (2R,6R)-2,6-dimethyl-4-[(3S)-2,2,4-trimethyl-7-nitro-3H-1-benzofuran-3-yl]morpholine
    —— (2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate —— C11H11O3-
    (2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate
    —— (3S,3aR,8bR)-3,3a-dimethyl-3,8b-dihydrocyclopenta[b][1]benzofuran —— C13H14O
    (3S,3aR,8bR)-3,3a-dimethyl-3,8b-dihydrocyclopenta[b][1]benzofuran
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperazine —— C13H18N2O
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperazine
    —— 1-[(2R,3R)-5-bromo-3-hydroxy-2-(1,2,4-triazol-1-yl)-3H-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one —— C15H16BrN3O3
    1-[(2R,3R)-5-bromo-3-hydroxy-2-(1,2,4-triazol-1-yl)-3H-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one
    —— 2,3-Dihydro-1-benzofuran-7-carboxylate —— C9H7O3-
    2,3-Dihydro-1-benzofuran-7-carboxylate
    —— (5aR,9aR)-5a-morpholin-4-ium-4-yl-7,8,9,9a-tetrahydro-6H-dibenzofuran-2-ol —— C16H22NO3+
    (5aR,9aR)-5a-morpholin-4-ium-4-yl-7,8,9,9a-tetrahydro-6H-dibenzofuran-2-ol
    —— (5aS,9aR)-5a-morpholin-4-ium-4-yl-7,8,9,9a-tetrahydro-6H-dibenzofuran-2-ol —— C16H22NO3+
    (5aS,9aR)-5a-morpholin-4-ium-4-yl-7,8,9,9a-tetrahydro-6H-dibenzofuran-2-ol
    —— (3R)-5-bromo-3-phenyl-3H-1-benzofuran-2-one —— C14H9BrO2
    (3R)-5-bromo-3-phenyl-3H-1-benzofuran-2-one
    —— 4-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]morpholin-4-ium —— C13H18NO2+
    4-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]morpholin-4-ium
    —— 4-[(2Z,3R)-2-benzylidene-5-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium —— C19H19N2O4+
    4-[(2Z,3R)-2-benzylidene-5-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium
    —— 3-(2,3-Dihydro-1-benzofuran-5-yl)propanoate —— C11H11O3-
    3-(2,3-Dihydro-1-benzofuran-5-yl)propanoate
    —— (5S)-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-5-(trifluoromethyl)-1,4-dihydropyrazol-5-ol —— C13H13F3N2O2
    (5S)-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-5-(trifluoromethyl)-1,4-dihydropyrazol-5-ol
    —— 2-(2,3-Dihydro-1-benzofuran-5-yl)-1,3-thiazole-4-carboxylate —— C12H8NO3S-
    2-(2,3-Dihydro-1-benzofuran-5-yl)-1,3-thiazole-4-carboxylate
    —— 2-[(benzylamino)methylidene]-1-benzofuran-3-thione —— C16H13NOS
    2-[(benzylamino)methylidene]-1-benzofuran-3-thione
    —— (1S,2S)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]cyclopropane-1-carboxylic acid —— C15H18O4
    (1S,2S)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]cyclopropane-1-carboxylic acid
    —— (1S,2R)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]cyclopropan-1-amine —— C14H19NO2
    (1S,2R)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]cyclopropan-1-amine
    —— (1S,2R)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]cyclopropane-1-carboxylic acid —— C15H18O4
    (1S,2R)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]cyclopropane-1-carboxylic acid
    —— (Z)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-thiophen-3-ylprop-2-enamide —— C19H22N2O2S
    (Z)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-thiophen-3-ylprop-2-enamide
    —— (Z)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(furan-2-yl)prop-2-enamide —— C17H17NO4
    (Z)-N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(furan-2-yl)prop-2-enamide
    —— (Z)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-thiophen-3-ylprop-2-enamide —— C19H22N2O2S
    (Z)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-thiophen-3-ylprop-2-enamide
    —— (Z)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(furan-2-yl)prop-2-enamide —— C17H17NO4
    (Z)-N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(furan-2-yl)prop-2-enamide
    —— methyl 2-[(3S)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]acetate —— C17H14O4
    methyl 2-[(3S)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]acetate
    —— 2-[(3R)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]acetic acid —— C16H12O4
    2-[(3R)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]acetic acid
    —— 2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazin-1-yl]ethyl N-(2,3-dihydro-1-benzofuran-5-ylmethyl)carbamate —— C26H35N3O4
    2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazin-1-yl]ethyl N-(2,3-dihydro-1-benzofuran-5-ylmethyl)carbamate
    —— 3-phenylprop-2-ynyl N-[[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]amino]carbamate —— C22H22N2O5
    3-phenylprop-2-ynyl N-[[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]amino]carbamate
    —— [4-(4-chlorophenyl)-1,3-thiazol-2-yl]methyl N-(2,3-dihydro-1-benzofuran-5-ylmethyl)carbamate —— C20H17ClN2O3S
    [4-(4-chlorophenyl)-1,3-thiazol-2-yl]methyl N-(2,3-dihydro-1-benzofuran-5-ylmethyl)carbamate
    —— (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-octanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H43FN2O7
    (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-octanoylamino]-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-octanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H46N2O8
    (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-octanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H33FN2O7
    (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H42N2O8
    (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[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-[cyclobutanecarbonyl-[(2,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H32Cl2N2O7
    (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl-[(2,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H33ClN2O7
    (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H31ClN2O7
    (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H44N2O8
    (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide