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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
    —— 1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile —— C20H21N3O3
    1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile
    —— (2S)-2-methyl-2,3-dihydro-1-benzofuran-4-ol —— C9H10O2
    (2S)-2-methyl-2,3-dihydro-1-benzofuran-4-ol
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylsulfanyl)acetamide —— C21H28N4O3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylsulfanyl)acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylsulfanyl)acetamide —— C21H28N4O3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-ylsulfanyl)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2,4,5-trimethoxyphenyl)methyl]acetamide —— C22H27NO6
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2,4,5-trimethoxyphenyl)methyl]acetamide
    —— (2R)-5,6-dimethyl-N-[2-(3-propan-2-yl-5-sulfanylidene-1H-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H24N4O2S
    (2R)-5,6-dimethyl-N-[2-(3-propan-2-yl-5-sulfanylidene-1H-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5,6-dimethyl-N-[2-(3-propan-2-yl-5-sulfanylidene-1H-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H24N4O2S
    (2S)-5,6-dimethyl-N-[2-(3-propan-2-yl-5-sulfanylidene-1H-1,2,4-triazol-4-yl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-3-(2-ethyl-6-methylphenyl)thiourea —— C19H21N3O2S
    1-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-3-(2-ethyl-6-methylphenyl)thiourea
    —— 2-[4-[(3R)-5-hydroxy-2-oxo-3H-1-benzofuran-3-yl]phenoxy]acetic acid —— C16H12O6
    2-[4-[(3R)-5-hydroxy-2-oxo-3H-1-benzofuran-3-yl]phenoxy]acetic acid
    —— N-[(E)-[(4-chlorophenyl)-(2,2-dimethyl-3H-1-benzofuran-5-yl)methylidene]amino]acetamide —— C19H19ClN2O2
    N-[(E)-[(4-chlorophenyl)-(2,2-dimethyl-3H-1-benzofuran-5-yl)methylidene]amino]acetamide
    —— (2R)-4-chloro-2-pyridin-2-yl-2,3-dihydro-1-benzofuran-7-amine —— C13H11ClN2O
    (2R)-4-chloro-2-pyridin-2-yl-2,3-dihydro-1-benzofuran-7-amine
    —— (2S)-4-chloro-2-pyridin-2-yl-2,3-dihydro-1-benzofuran-7-amine —— C13H11ClN2O
    (2S)-4-chloro-2-pyridin-2-yl-2,3-dihydro-1-benzofuran-7-amine
    —— N-[(Z)-[(2,2-dimethyl-3H-1-benzofuran-5-yl)-(4-fluorophenyl)methylidene]amino]cyclopropanecarboxamide —— C21H21FN2O2
    N-[(Z)-[(2,2-dimethyl-3H-1-benzofuran-5-yl)-(4-fluorophenyl)methylidene]amino]cyclopropanecarboxamide
    —— (2R)-2-pyridin-3-yl-2,3-dihydro-1-benzofuran-4-carboxylic acid —— C14H11NO3
    (2R)-2-pyridin-3-yl-2,3-dihydro-1-benzofuran-4-carboxylic acid
    —— (2S)-2-pyridin-3-yl-2,3-dihydro-1-benzofuran-4-carboxylic acid —— C14H11NO3
    (2S)-2-pyridin-3-yl-2,3-dihydro-1-benzofuran-4-carboxylic acid
    —— (1R,4aS,9bS)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile —— C15H15NO2
    (1R,4aS,9bS)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile
    —— (1R,4aS,9bR)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile —— C15H15NO2
    (1R,4aS,9bR)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile
    —— (1S,4aS,9bS)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile —— C15H15NO2
    (1S,4aS,9bS)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile
    —— (1S,4aS,9bR)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile —— C15H15NO2
    (1S,4aS,9bR)-8,9b-dimethyl-3-oxo-1,2,4,4a-tetrahydrodibenzofuran-1-carbonitrile
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2R)-2-(furan-2-yl)-2-hydroxypropyl]acetamide —— C19H23NO5
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2R)-2-(furan-2-yl)-2-hydroxypropyl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2S)-2-(furan-2-yl)-2-hydroxypropyl]acetamide —— C19H23NO5
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2S)-2-(furan-2-yl)-2-hydroxypropyl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2R)-2-hydroxy-2-thiophen-2-ylethyl]acetamide —— C18H21NO4S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2R)-2-hydroxy-2-thiophen-2-ylethyl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]acetamide —— C18H21NO4S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(ethylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C18H24N4O3S2
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(ethylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
    —— 4-bromo-N-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1H-pyrazole-5-carboxamide —— C14H14BrN3O2
    4-bromo-N-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1H-pyrazole-5-carboxamide
    —— methyl 3-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-5-methyl-1H-pyrrole-2-carboxylate —— C16H16N2O4
    methyl 3-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-5-methyl-1H-pyrrole-2-carboxylate
    —— 4-bromo-N-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1H-pyrazole-5-carboxamide —— C14H14BrN3O2
    4-bromo-N-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1H-pyrazole-5-carboxamide
    —— (2S)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-2-imidazol-1-ylpropanamide —— C17H16N4O2S
    (2S)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-2-imidazol-1-ylpropanamide
    —— methyl 3-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-5-methyl-1H-pyrrole-2-carboxylate —— C16H16N2O4
    methyl 3-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-5-methyl-1H-pyrrole-2-carboxylate
    —— 5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-3-(1-methylpyrazol-4-yl)-1,2,4-oxadiazole —— C14H12N4O2
    5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-3-(1-methylpyrazol-4-yl)-1,2,4-oxadiazole
    —— 5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-3-(1-methylpyrazol-4-yl)-1,2,4-oxadiazole —— C14H12N4O2
    5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-3-(1-methylpyrazol-4-yl)-1,2,4-oxadiazole
    —— (2R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-2-imidazol-1-ylpropanamide —— C17H16N4O2S
    (2R)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-2-imidazol-1-ylpropanamide
    —— (2S)-N-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H24N2O3
    (2S)-N-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H25N2O3+
    (2R)-N-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[(2S)-4-ethylmorpholin-2-yl]-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine —— C18H28N2O3
    1-[(2S)-4-ethylmorpholin-2-yl]-N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine
    —— (2R)-N-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H24N2O3
    (2R)-N-[[2-(morpholin-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2S)-1-pyridazin-3-ylpyrrolidin-2-yl]methanamine —— C18H22N4O
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2S)-1-pyridazin-3-ylpyrrolidin-2-yl]methanamine
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2R)-1-pyridazin-3-ylpyrrolidin-2-yl]methanamine —— C18H22N4O
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-[(2R)-1-pyridazin-3-ylpyrrolidin-2-yl]methanamine
    —— (2S)-N-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H25N2O3+
    (2S)-N-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[[4-(dimethylamino)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H20N2O2
    (2R)-N-[[4-(dimethylamino)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]ethanone —— C20H25N3O2
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]ethanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]ethanone —— C20H25N3O2
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]ethanone
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone —— C19H23N3O2
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone —— C19H23N3O2
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone —— C19H23N3O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone —— C19H23N3O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methanone
    —— 1-cyclopropyl-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(pyridin-2-ylmethyl)guanidine —— C19H22N4O
    1-cyclopropyl-3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(pyridin-2-ylmethyl)guanidine
    —— 1-cyclopropyl-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(pyridin-2-ylmethyl)guanidine —— C19H22N4O
    1-cyclopropyl-3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(pyridin-2-ylmethyl)guanidine
    —— (2S)-N-[6-(trifluoromethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H11F3N2O2
    (2S)-N-[6-(trifluoromethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[6-(trifluoromethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H11F3N2O2
    (2R)-N-[6-(trifluoromethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide