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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-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-nitro-1,2,4-triazole —— C14H16N4O4
    1-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-nitro-1,2,4-triazole
    —— 4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(R)-methylsulfinyl]-1,2,4-triazole —— C15H19N3O3S
    4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(R)-methylsulfinyl]-1,2,4-triazole
    —— 4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(S)-methylsulfinyl]-1,2,4-triazole —— C15H19N3O3S
    4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(S)-methylsulfinyl]-1,2,4-triazole
    —— 4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(S)-methylsulfinyl]-1,2,4-triazole —— C15H19N3O3S
    4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(S)-methylsulfinyl]-1,2,4-triazole
    —— 1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-nitro-1,2,4-triazole —— C14H16N4O4
    1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-nitro-1,2,4-triazole
    —— 1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole-3-carbonitrile —— C15H16N4O2
    1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole-3-carbonitrile
    —— 1-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole-3-carbonitrile —— C15H16N4O2
    1-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,2,4-triazole-3-carbonitrile
    —— 5-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxymethyl]-3-[(1S)-1-ethoxyethyl]-1,2,4-oxadiazole —— C17H22N2O4
    5-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxymethyl]-3-[(1S)-1-ethoxyethyl]-1,2,4-oxadiazole
    —— 5-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxymethyl]-3-[(1R)-1-ethoxyethyl]-1,2,4-oxadiazole —— C17H22N2O4
    5-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxymethyl]-3-[(1R)-1-ethoxyethyl]-1,2,4-oxadiazole
    —— 3-(1,3-dimethylpyrazol-4-yl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide —— C19H25N3O3
    3-(1,3-dimethylpyrazol-4-yl)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide
    —— 3-(1,3-dimethylpyrazol-4-yl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide —— C19H25N3O3
    3-(1,3-dimethylpyrazol-4-yl)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide
    —— (3R)-N-[3-(cyclopropylcarbamoyl)thiophen-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H16N2O3S
    (3R)-N-[3-(cyclopropylcarbamoyl)thiophen-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[3-(cyclopropylcarbamoyl)thiophen-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H16N2O3S
    (3S)-N-[3-(cyclopropylcarbamoyl)thiophen-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— N-[(S)-2,3-dihydro-1-benzofuran-5-yl(pyridin-3-yl)methyl]-N-ethyl-2-methoxyacetamide —— C19H22N2O3
    N-[(S)-2,3-dihydro-1-benzofuran-5-yl(pyridin-3-yl)methyl]-N-ethyl-2-methoxyacetamide
    —— N-[(R)-2,3-dihydro-1-benzofuran-5-yl(pyridin-3-yl)methyl]-N-ethyl-2-methoxyacetamide —— C19H22N2O3
    N-[(R)-2,3-dihydro-1-benzofuran-5-yl(pyridin-3-yl)methyl]-N-ethyl-2-methoxyacetamide
    —— (Z)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-3-pyridin-2-ylprop-2-enamide —— C19H15N3O2S
    (Z)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-3-pyridin-2-ylprop-2-enamide
    —— (Z)-3-(5-chloro-1,3-dimethylpyrazol-4-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide —— C20H24ClN3O3
    (Z)-3-(5-chloro-1,3-dimethylpyrazol-4-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide
    —— (Z)-3-(5-chloro-1,3-dimethylpyrazol-4-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide —— C20H24ClN3O3
    (Z)-3-(5-chloro-1,3-dimethylpyrazol-4-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide
    —— N-[(2R)-2-(3-fluorophenyl)-2-methoxyethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C17H18FNO4S
    N-[(2R)-2-(3-fluorophenyl)-2-methoxyethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— N-[(2S)-2-(3-fluorophenyl)-2-methoxyethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C17H18FNO4S
    N-[(2S)-2-(3-fluorophenyl)-2-methoxyethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[4-(thiophene-2-carbonyl)piperazin-1-yl]ethanone —— C21H24N2O4S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[4-(thiophene-2-carbonyl)piperazin-1-yl]ethanone
    —— (2R,7R)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene —— C12H10O5
    (2R,7R)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene
    —— (2R,7S)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene —— C12H10O5
    (2R,7S)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene
    —— (2S,7R)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene —— C12H10O5
    (2S,7R)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene
    —— (2S,7S)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene —— C12H10O5
    (2S,7S)-11,13-dimethoxy-4,6,8-trioxatetracyclo[7.4.0.02,7.03,5]trideca-1(9),3(5),10,12-tetraene
    —— 2-[(5-amino-1H-1,2,4-triazol-3-yl)sulfanyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C16H21N5O3S
    2-[(5-amino-1H-1,2,4-triazol-3-yl)sulfanyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— (5aR,9aS)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1,2-diol —— C12H14O3
    (5aR,9aS)-5a,6,7,8,9,9a-hexahydrodibenzofuran-1,2-diol
    —— N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4,6-dimethylpyrimidin-2-amine —— C18H22N4O2
    N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4,6-dimethylpyrimidin-2-amine
    —— 2-[(2Z)-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one —— C17H20N4O3
    2-[(2Z)-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one
    —— 2-[(2Z)-2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one —— C17H20N4O3
    2-[(2Z)-2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one
    —— ethyl (5Z)-2-anilino-5-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylidene]-4-oxofuran-3-carboxylate —— C24H23NO6
    ethyl (5Z)-2-anilino-5-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylidene]-4-oxofuran-3-carboxylate
    —— (Z)-3-[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-pyridin-2-ylprop-2-enenitrile —— C18H16N2O2
    (Z)-3-[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-pyridin-2-ylprop-2-enenitrile
    —— ethyl (5Z)-2-anilino-5-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylidene]-4-oxofuran-3-carboxylate —— C24H23NO6
    ethyl (5Z)-2-anilino-5-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methylidene]-4-oxofuran-3-carboxylate
    —— (Z)-3-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-pyridin-2-ylprop-2-enenitrile —— C18H16N2O2
    (Z)-3-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-pyridin-2-ylprop-2-enenitrile
    —— (2E,5E)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(3,3-dimethyl-2-oxobutylidene)-3-methyl-1,3-thiazolidin-4-one —— C19H21NO3S
    (2E,5E)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(3,3-dimethyl-2-oxobutylidene)-3-methyl-1,3-thiazolidin-4-one
    —— (2E,5Z)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(3,3-dimethyl-2-oxobutylidene)-3-methyl-1,3-thiazolidin-4-one —— C19H21NO3S
    (2E,5Z)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(3,3-dimethyl-2-oxobutylidene)-3-methyl-1,3-thiazolidin-4-one
    —— (2S,3R)-3-methyl-N-[(Z)-2-phenylethenyl]sulfonyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H17NO4S
    (2S,3R)-3-methyl-N-[(Z)-2-phenylethenyl]sulfonyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S,3S)-3-methyl-N-[(Z)-2-phenylethenyl]sulfonyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H17NO4S
    (2S,3S)-3-methyl-N-[(Z)-2-phenylethenyl]sulfonyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (5E)-5-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one —— C18H20N2O3S
    (5E)-5-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one
    —— 2-chloro-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide —— C12H14ClNO2
    2-chloro-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide
    —— (Z)-3-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide —— C17H14ClN3O2S
    (Z)-3-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide
    —— (Z)-3-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide —— C17H14ClN3O2S
    (Z)-3-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]methanone —— C22H25N2O3+
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]methanone
    —— 4-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxymethyl]-2-thiophen-2-yl-1,3-oxazole —— C18H17NO3S
    4-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxymethyl]-2-thiophen-2-yl-1,3-oxazole
    —— methyl (3R)-3-[3-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxo-1,2-dihydropyrazol-4-yl]-3-pyridin-3-ylpropanoate —— C21H21N3O4
    methyl (3R)-3-[3-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxo-1,2-dihydropyrazol-4-yl]-3-pyridin-3-ylpropanoate
    —— methyl (3S)-3-[3-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxo-1,2-dihydropyrazol-4-yl]-3-(furan-2-yl)propanoate —— C20H20N2O5
    methyl (3S)-3-[3-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxo-1,2-dihydropyrazol-4-yl]-3-(furan-2-yl)propanoate
    —— 3-(3,5-dimethylpyrazol-1-yl)-4-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1H-1,2,4-triazole-5-thione —— C19H22N6O2S
    3-(3,5-dimethylpyrazol-1-yl)-4-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1H-1,2,4-triazole-5-thione
    —— (2R)-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H17NO2
    (2R)-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H17NO2
    (2R)-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H17NO2
    (2S)-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide