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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-(4-cyanophenoxy)-N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C21H21N3O4
    2-(4-cyanophenoxy)-N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(2-fluorophenoxy)acetamide —— C20H21FN2O4
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(2-fluorophenoxy)acetamide
    —— 2-(2,5-dimethylphenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C22H26N2O4
    2-(2,5-dimethylphenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— 2-(2,5-dimethylphenoxy)-N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C22H26N2O4
    2-(2,5-dimethylphenoxy)-N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(4-methoxyphenoxy)acetamide —— C21H24N2O5
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(4-methoxyphenoxy)acetamide
    —— 2-(2-chlorophenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C20H21ClN2O4
    2-(2-chlorophenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— N-cyclopropyl-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(4-methoxyphenyl)methyl]acetamide —— C23H27NO4
    N-cyclopropyl-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(4-methoxyphenyl)methyl]acetamide
    —— 4-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1,2,4-triazolidine-3,5-dithione —— C14H16N4O2S2
    4-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1,2,4-triazolidine-3,5-dithione
    —— (2S,3S)-N-[(1-benzyl-3,5-dimethylpyrazol-4-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C24H27N3O2
    (2S,3S)-N-[(1-benzyl-3,5-dimethylpyrazol-4-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(1-oxidopyridin-1-ium-2-yl)sulfanylacetamide —— C19H22N2O4S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(1-oxidopyridin-1-ium-2-yl)sulfanylacetamide
    —— (2S)-1-(1-adamantyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-one —— C23H30O3
    (2S)-1-(1-adamantyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]propan-1-one
    —— (Z)-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylsulfonylprop-2-enenitrile —— C15H17NO4S
    (Z)-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylsulfonylprop-2-enenitrile
    —— (Z)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylsulfonylprop-2-enenitrile —— C15H17NO4S
    (Z)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-methylsulfonylprop-2-enenitrile
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methyl-N-(1-methylpiperidin-4-yl)acetamide —— C19H28N2O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-methyl-N-(1-methylpiperidin-4-yl)acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1R)-1-(2-methoxy-5-methylphenyl)ethyl]acetamide —— C22H27NO4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1R)-1-(2-methoxy-5-methylphenyl)ethyl]acetamide
    —— (Z)-3-pyridin-2-yl-N-[[(2S)-7-pyrimidin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide —— C21H18N4O2
    (Z)-3-pyridin-2-yl-N-[[(2S)-7-pyrimidin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide
    —— (Z)-N-[[(2R)-7-(6-methoxypyridazin-3-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-pyridin-4-ylprop-2-enamide —— C23H22N4O3
    (Z)-N-[[(2R)-7-(6-methoxypyridazin-3-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-pyridin-4-ylprop-2-enamide
    —— (Z)-3-pyridin-2-yl-N-[[(2R)-7-pyrimidin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide —— C21H18N4O2
    (Z)-3-pyridin-2-yl-N-[[(2R)-7-pyrimidin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methyl]prop-2-enamide
    —— (Z)-N-[[(2R)-7-(3,6-dimethylpyrazin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide —— C22H20FN3O2S
    (Z)-N-[[(2R)-7-(3,6-dimethylpyrazin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide
    —— (Z)-N-[[(2S)-7-(3,6-dimethylpyrazin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide —— C22H20FN3O2S
    (Z)-N-[[(2S)-7-(3,6-dimethylpyrazin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide
    —— (Z)-N-[[(2R)-7-(3-methylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide —— C22H20N2O2S
    (Z)-N-[[(2R)-7-(3-methylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide
    —— (Z)-N-[[(2S)-7-(3-methylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide —— C22H20N2O2S
    (Z)-N-[[(2S)-7-(3-methylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-thiophen-2-ylprop-2-enamide
    —— N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-fluorophenoxy)acetamide —— C20H21FN2O4
    N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-fluorophenoxy)acetamide
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-fluorophenoxy)acetamide —— C20H21FN2O4
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-fluorophenoxy)acetamide
    —— (2S,3R)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C10H11NO6S
    (2S,3R)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— (2S,3S)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C10H11NO6S
    (2S,3S)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— (2S,3S)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C9H9NO6S
    (2S,3S)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— (2R,3S)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C10H11NO6S
    (2R,3S)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— (2R,3R)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C9H9NO6S
    (2R,3R)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— (2S,3R)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C9H9NO6S
    (2S,3R)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— (2R,3R)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C10H11NO6S
    (2R,3R)-3-ethylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— (2R,3S)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol —— C9H9NO6S
    (2R,3S)-3-methylsulfonyl-5-nitro-2,3-dihydro-1-benzofuran-2-ol
    —— 2-(3-chloro-4-fluorophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H21ClFNO4
    2-(3-chloro-4-fluorophenoxy)-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-pyrimidin-2-ylsulfanylacetamide —— C18H21N3O3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-pyrimidin-2-ylsulfanylacetamide
    —— 1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2S)-oxan-2-yl]propyl]urea —— C17H22F2N2O3
    1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2S)-oxan-2-yl]propyl]urea
    —— 1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2R)-oxan-2-yl]propyl]urea —— C17H22F2N2O3
    1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2R)-oxan-2-yl]propyl]urea
    —— 1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2R)-oxan-2-yl]propyl]urea —— C17H22F2N2O3
    1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2R)-oxan-2-yl]propyl]urea
    —— 1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2S)-oxan-2-yl]propyl]urea —— C17H22F2N2O3
    1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[3-[(2S)-oxan-2-yl]propyl]urea
    —— 1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-2-(1,3-thiazol-2-yl)propyl]urea —— C15H15F2N3O2S
    1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-2-(1,3-thiazol-2-yl)propyl]urea
    —— 1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-2-(1,3-thiazol-2-yl)propyl]urea —— C15H15F2N3O2S
    1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[(2S)-2-(1,3-thiazol-2-yl)propyl]urea
    —— 1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-2-(1,3-thiazol-2-yl)propyl]urea —— C15H15F2N3O2S
    1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-[(2R)-2-(1,3-thiazol-2-yl)propyl]urea
    —— 5-chloro-N-[(1R)-1-pyridin-4-ylethyl]-2,3-dihydro-1-benzofuran-7-sulfonamide —— C15H15ClN2O3S
    5-chloro-N-[(1R)-1-pyridin-4-ylethyl]-2,3-dihydro-1-benzofuran-7-sulfonamide
    —— 1-[(3R)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)sulfonyl]pyrrolidin-3-yl]-N,N-dimethylmethanamine —— C15H21ClN2O3S
    1-[(3R)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)sulfonyl]pyrrolidin-3-yl]-N,N-dimethylmethanamine
    —— 1-[(3S)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)sulfonyl]pyrrolidin-3-yl]-N,N-dimethylmethanamine —— C15H21ClN2O3S
    1-[(3S)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)sulfonyl]pyrrolidin-3-yl]-N,N-dimethylmethanamine
    —— (2R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-methylsulfonylpropan-2-amine —— C14H20ClNO3S
    (2R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-methylsulfonylpropan-2-amine
    —— (2S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-methylsulfonylpropan-2-amine —— C14H20ClNO3S
    (2S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-methylsulfonylpropan-2-amine
    —— (2S)-1-[4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperazin-1-yl]-2-hydroxypropan-1-one —— C16H21ClN2O3
    (2S)-1-[4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperazin-1-yl]-2-hydroxypropan-1-one
    —— (2R)-1-[4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperazin-1-yl]-2-hydroxypropan-1-one —— C16H21ClN2O3
    (2R)-1-[4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperazin-1-yl]-2-hydroxypropan-1-one
    —— (E)-2-(4-chlorophenyl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]ethenesulfonamide —— C20H22ClNO4S
    (E)-2-(4-chlorophenyl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]ethenesulfonamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide —— C17H22N2O5S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide