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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
    —— N-[(1S)-1-(3-chlorophenyl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C20H22ClNO3
    N-[(1S)-1-(3-chlorophenyl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— N-cyclopentyl-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C17H23NO3
    N-cyclopentyl-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
    —— (E)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylsulfonylprop-2-enenitrile —— C15H17NO4S
    (E)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylsulfonylprop-2-enenitrile
    —— ethyl 2-cyano-3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylimino]propanoate —— C18H22N2O4
    ethyl 2-cyano-3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylimino]propanoate
    —— (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-methyl-1,3-thiazolidin-4-one —— C22H27NO4S
    (2Z,5Z)-2-(3,3-dimethyl-2-oxobutylidene)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-3-methyl-1,3-thiazolidin-4-one
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4,5,6-trimethylpyrimidin-2-yl)sulfanylacetamide —— C21H27N3O3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4,5,6-trimethylpyrimidin-2-yl)sulfanylacetamide
    —— 2-(4,6-diaminopyrimidin-2-yl)sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H23N5O3S
    2-(4,6-diaminopyrimidin-2-yl)sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-(4,6-diaminopyrimidin-2-yl)sulfanyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H23N5O3S
    2-(4,6-diaminopyrimidin-2-yl)sulfanyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-(2,4-difluorophenyl)sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H21F2NO3S
    2-(2,4-difluorophenyl)sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-methyl-N-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-4-oxo-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepine-7-carboxamide —— C19H22N4O3
    2-methyl-N-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-4-oxo-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepine-7-carboxamide
    —— 1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-3-[2-(2-oxo-1,3-oxazinan-3-yl)ethyl]urea —— C16H21N3O4
    1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-3-[2-(2-oxo-1,3-oxazinan-3-yl)ethyl]urea
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-nitropyridin-3-yl)oxyacetamide —— C19H21N3O6
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-nitropyridin-3-yl)oxyacetamide
    —— [2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl] pyrrolidine-1-carbodithioate —— C19H26N2O3S2
    [2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl] pyrrolidine-1-carbodithioate
    —— 4-chloro-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-phenylpyridazin-3-one —— C22H22ClN3O3
    4-chloro-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-phenylpyridazin-3-one
    —— 2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-6-fluorobenzonitrile —— C19H19FN2O2
    2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-6-fluorobenzonitrile
    —— N-(4-chlorophenethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C20H22ClNO3
    N-(4-chlorophenethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2-methoxyphenyl)methyl]acetamide —— C20H23NO4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(2-methoxyphenyl)methyl]acetamide
    —— N-(2-(diethylamino)ethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C18H28N2O3
    N-(2-(diethylamino)ethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[(2S,6S)-2,6-dimethylmorpholin-4-yl]ethanone —— C18H25NO4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[(2S,6S)-2,6-dimethylmorpholin-4-yl]ethanone
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1S,2R)-2-methylcyclohexyl]acetamide —— C19H27NO3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1S,2R)-2-methylcyclohexyl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-morpholin-4-ylethanone —— C16H21NO4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-morpholin-4-ylethanone
    —— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(thiophen-2-ylmethyl)acetamide —— C17H19NO3S
    2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(thiophen-2-ylmethyl)acetamide
    —— N-benzyl-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methylacetamide —— C20H23NO3
    N-benzyl-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methylacetamide
    —— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(4-methylpyrimidin-2-yl)acetamide —— C17H19N3O3
    2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(4-methylpyrimidin-2-yl)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N,N-dimethylacetamide —— C14H19NO3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N,N-dimethylacetamide
    —— N-(3-(diethylamino)propyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C19H30N2O3
    N-(3-(diethylamino)propyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1R,5S)-3,3,5-trimethylcyclohexyl]acetamide —— C21H31NO3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1R,5S)-3,3,5-trimethylcyclohexyl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-pyrimidin-2-ylacetamide —— C16H17N3O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-pyrimidin-2-ylacetamide
    —— (2S)-N-[[1-[(3S)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H25N3O4S
    (2S)-N-[[1-[(3S)-1,1-dioxothiolan-3-yl]-3,5-dimethylpyrazol-4-yl]methyl]-N-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(3,4,5-trimethoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H21NO5
    (2S)-N-[(3,4,5-trimethoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(3-methylsulfanylpropyl)piperazine-1-carbothioamide —— C18H27N3OS2
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(3-methylsulfanylpropyl)piperazine-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(furan-2-ylmethyl)piperazine-1-carbothioamide —— C19H23N3O2S
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(furan-2-ylmethyl)piperazine-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(3-methylsulfanylpropyl)piperazin-4-ium-1-carbothioamide —— C18H28N3OS2+
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(3-methylsulfanylpropyl)piperazin-4-ium-1-carbothioamide
    —— N-cyclopropyl-4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-carbothioamide —— C17H24N3OS+
    N-cyclopropyl-4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-[[(2S)-oxolan-2-yl]methyl]piperazin-4-ium-1-carbothioamide —— C19H28N3O2S+
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-[[(2S)-oxolan-2-yl]methyl]piperazin-4-ium-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-[(4-methoxyphenyl)methyl]piperazin-4-ium-1-carbothioamide —— C22H28N3O2S+
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-[(4-methoxyphenyl)methyl]piperazin-4-ium-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(3-morpholin-4-ium-4-ylpropyl)piperazin-4-ium-1-carbothioamide —— C21H34N4O2S+2
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(3-morpholin-4-ium-4-ylpropyl)piperazin-4-ium-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-[[(2R)-oxolan-2-yl]methyl]piperazine-1-carbothioamide —— C19H27N3O2S
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-[[(2R)-oxolan-2-yl]methyl]piperazine-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-propan-2-ylpiperazine-1-carbothioamide —— C17H25N3OS
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-propan-2-ylpiperazine-1-carbothioamide
    —— 4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(2-phenylethyl)piperazin-4-ium-1-carbothioamide —— C22H28N3OS+
    4-(2,3-dihydro-1-benzofuran-5-ylmethyl)-N-(2-phenylethyl)piperazin-4-ium-1-carbothioamide
    —— 2-(2-bromophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H22BrNO4
    2-(2-bromophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(prop-2-enylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C19H24N4O3S2
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(prop-2-enylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(methylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C17H22N4O3S2
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(methylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
    —— 1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(4-fluorophenyl)methyl]thiourea —— C20H23FN2O2S
    1-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[(4-fluorophenyl)methyl]thiourea
    —— (5Z)-2-anilino-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxofuran-3-carboxylate —— C23H20NO6-
    (5Z)-2-anilino-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxofuran-3-carboxylate
    —— 3-[(E)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile —— C19H19N3O3
    3-[(E)-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethenyl]-4-methyl-6-oxo-1H-pyridazine-5-carbonitrile
    —— 2-[(4-amino-5-methyl-1,2,4-triazol-3-yl)sulfanyl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C17H23N5O3S
    2-[(4-amino-5-methyl-1,2,4-triazol-3-yl)sulfanyl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile —— C20H21N3O3
    1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-4,6-dimethyl-2-oxopyridine-3-carbonitrile
    —— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-3-(2-ethyl-6-methylphenyl)thiourea —— C19H21N3O2S
    1-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-3-(2-ethyl-6-methylphenyl)thiourea
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(thiophene-2-carbonyl)piperazin-1-yl]methanone —— C18H18N2O3S
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(thiophene-2-carbonyl)piperazin-1-yl]methanone