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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
    —— (3R)-1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]-3-(hydroxymethyl)piperidin-3-ol —— C17H25NO3
    (3R)-1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]-3-(hydroxymethyl)piperidin-3-ol
    —— 1-[2-(diethylamino)-2-oxoethyl]-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyltriazole-4-carboxamide —— C19H25N5O3
    1-[2-(diethylamino)-2-oxoethyl]-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyltriazole-4-carboxamide
    —— 1-[2-(diethylamino)-2-oxoethyl]-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyltriazole-4-carboxamide —— C19H25N5O3
    1-[2-(diethylamino)-2-oxoethyl]-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyltriazole-4-carboxamide
    —— 2-[(3S)-4-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]morpholin-3-yl]acetic acid —— C17H23NO4
    2-[(3S)-4-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]morpholin-3-yl]acetic acid
    —— 2,3-dihydro-1-benzofuran-5-yl-[(4S)-4-[(dimethylamino)methyl]-4-hydroxyazepan-1-yl]methanone —— C18H26N2O3
    2,3-dihydro-1-benzofuran-5-yl-[(4S)-4-[(dimethylamino)methyl]-4-hydroxyazepan-1-yl]methanone
    —— 2,3-dihydro-1-benzofuran-5-yl-[(4R)-4-[(dimethylamino)methyl]-4-hydroxyazepan-1-yl]methanone —— C18H26N2O3
    2,3-dihydro-1-benzofuran-5-yl-[(4R)-4-[(dimethylamino)methyl]-4-hydroxyazepan-1-yl]methanone
    —— (3S)-3-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-2,3-dihydrothiophene 1,1-dioxide —— C17H18N2O3S
    (3S)-3-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-2,3-dihydrothiophene 1,1-dioxide
    —— (3R)-3-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-2,3-dihydrothiophene 1,1-dioxide —— C17H18N2O3S
    (3R)-3-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-2,3-dihydrothiophene 1,1-dioxide
    —— 4-[(3R)-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-6-one —— C21H27N3O2
    4-[(3R)-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-6-one
    —— 4-[(3S)-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-6-one —— C21H27N3O2
    4-[(3S)-1-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]piperidin-3-yl]-2-methyl-1H-pyrimidin-6-one
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-(3-pyridin-4-ylazetidin-1-yl)methanone —— C17H16N2O2
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-(3-pyridin-4-ylazetidin-1-yl)methanone
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-(3-pyridin-4-ylazetidin-1-yl)methanone —— C17H16N2O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-(3-pyridin-4-ylazetidin-1-yl)methanone
    —— 2-cyclopentyl-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-amine —— C21H26N4O
    2-cyclopentyl-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-amine
    —— 2-cyclopentyl-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-amine —— C21H26N4O
    2-cyclopentyl-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-amine
    —— (2R)-5-chloro-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16ClNO3
    (2R)-5-chloro-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-cycloheptyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H20ClNO2
    (2S)-5-chloro-N-cycloheptyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-cycloheptyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H20ClNO2
    (2R)-5-chloro-N-cycloheptyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16ClNO3
    (2S)-5-chloro-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]acetamide —— C17H23NO5S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]acetamide
    —— 3-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C18H18NO5S2-
    3-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
    —— 4-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate —— C19H20NO5S2-
    4-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate
    —— 4-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate —— C19H20NO5S2-
    4-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate
    —— 3-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C18H19NO5S2
    3-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
    —— 4-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C19H21NO5S2
    4-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
    —— 3-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C18H19NO5S2
    3-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
    —— 4-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid —— C19H21NO5S2
    4-[(5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
    —— 3-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C18H18NO5S2-
    3-[(5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
    —— (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidin-4-one —— C21H25NO4S
    (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidin-4-one
    —— (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidin-4-one —— C21H25NO4S
    (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidin-4-one
    —— 2-[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide —— C20H19ClN2O3S2
    2-[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide
    —— 2-[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide —— C20H19ClN2O3S2
    2-[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide
    —— (2S)-N-[(R)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H16ClNO2S
    (2S)-N-[(R)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(R)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H16ClNO2S
    (2R)-N-[(R)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(S)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H16ClNO2S
    (2S)-N-[(S)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(S)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H16ClNO2S
    (2R)-N-[(S)-(4-chlorophenyl)-thiophen-3-ylmethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(4-methylthiazol-2-yl)acetamide —— C16H18N2O3S
    2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(4-methylthiazol-2-yl)acetamide
    —— N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethoxyphenyl)propanamide —— C22H27NO4
    N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethoxyphenyl)propanamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-methyl-2-[(3R)-3-methylpiperidin-1-yl]propyl]acetamide —— C22H34N2O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-methyl-2-[(3R)-3-methylpiperidin-1-yl]propyl]acetamide
    —— (2R)-N-[[1-(2-methoxyphenyl)cyclopentyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C22H25NO3
    (2R)-N-[[1-(2-methoxyphenyl)cyclopentyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(2S)-4-(4-bromophenyl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H20BrNO2
    (2S)-N-[(2S)-4-(4-bromophenyl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2R)-4-(4-bromophenyl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H20BrNO2
    (2R)-N-[(2R)-4-(4-bromophenyl)butan-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2R)-1-(1,2,4-triazol-1-yl)propan-2-yl]acetamide —— C17H22N4O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2R)-1-(1,2,4-triazol-1-yl)propan-2-yl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[[(3S)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]methyl]acetamide —— C19H25F3N2O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[[(3S)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]methyl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[[(3R)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]methyl]acetamide —— C19H25F3N2O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[[(3R)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]methyl]acetamide
    —— (E)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylpent-2-enamide —— C17H23NO3
    (E)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylpent-2-enamide
    —— (2S)-2-butylsulfanyl-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide —— C18H27NO3S
    (2S)-2-butylsulfanyl-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide
    —— (2R)-2-butylsulfanyl-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]propanamide —— C18H22N2O2S2
    (2R)-2-butylsulfanyl-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]propanamide
    —— (2R)-2-butylsulfanyl-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide —— C18H27NO3S
    (2R)-2-butylsulfanyl-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide
    —— (2S)-2-butylsulfanyl-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]propanamide —— C18H22N2O2S2
    (2S)-2-butylsulfanyl-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]propanamide
    —— (2R)-2-butylsulfanyl-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide —— C18H27NO3S
    (2R)-2-butylsulfanyl-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]propanamide