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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
    —— [5-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-5-oxopentyl]urea —— C19H29N4O3+
    [5-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-5-oxopentyl]urea
    —— (2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-methylphenyl)sulfanylpropan-1-one —— C23H29N2O2S+
    (2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-methylphenyl)sulfanylpropan-1-one
    —— 2-(2,5-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]ethanone —— C21H23F2N2O2S+
    2-(2,5-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]ethanone
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(1-methylpyrazol-4-yl)methanone —— C18H23N4O2+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(1-methylpyrazol-4-yl)methanone
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(5-methyl-4-propylthiophen-2-yl)methanone —— C22H28N2O2S
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(5-methyl-4-propylthiophen-2-yl)methanone
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-[5-(2-fluorophenyl)furan-2-yl]methanone —— C24H24FN2O3+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-[5-(2-fluorophenyl)furan-2-yl]methanone
    —— 4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-oxoethoxy]-3-methoxybenzaldehyde —— C23H26N2O5
    4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-oxoethoxy]-3-methoxybenzaldehyde
    —— 1-[3-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-oxopropyl]pyrrolidine-2,5-dione —— C20H26N3O4+
    1-[3-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-oxopropyl]pyrrolidine-2,5-dione
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(3,5-dimethyl-1,2-oxazol-4-yl)propan-1-one —— C21H27N3O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(3,5-dimethyl-1,2-oxazol-4-yl)propan-1-one
    —— (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(3-methylthiophen-2-yl)prop-2-en-1-one —— C21H25N2O2S+
    (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(3-methylthiophen-2-yl)prop-2-en-1-one
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(5-ethyl-4-methylthiophen-2-yl)methanone —— C21H26N2O2S
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(5-ethyl-4-methylthiophen-2-yl)methanone
    —— 1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-[(3R)-1,1-dioxothiolan-3-yl]sulfanylethanone —— C19H27N2O4S2+
    1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-[(3R)-1,1-dioxothiolan-3-yl]sulfanylethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-4-(4-methoxyphenoxy)butan-1-one —— C24H31N2O4+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-4-(4-methoxyphenoxy)butan-1-one
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(4-ethyl-5-methylthiophen-2-yl)methanone —— C21H27N2O2S+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(4-ethyl-5-methylthiophen-2-yl)methanone
    —— 1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(3R)-1,1-dioxothiolan-3-yl]ethanone —— C19H26N2O4S
    1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(3R)-1,1-dioxothiolan-3-yl]ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-methoxyphenyl)sulfanylethanone —— C22H27N2O3S+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-methoxyphenyl)sulfanylethanone
    —— (1-Benzylpyrazol-4-yl)-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]methanone —— C24H27N4O2+
    (1-Benzylpyrazol-4-yl)-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]methanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(2-methoxyphenyl)propan-1-one —— C23H28N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(2-methoxyphenyl)propan-1-one
    —— (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(3-methylthiophen-2-yl)prop-2-en-1-one —— C21H24N2O2S
    (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(3-methylthiophen-2-yl)prop-2-en-1-one
    —— 4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-oxoethoxy]-3-methoxybenzaldehyde —— C23H27N2O5+
    4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-oxoethoxy]-3-methoxybenzaldehyde
    —— (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-thiophen-2-ylprop-2-en-1-one —— C20H23N2O2S+
    (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-thiophen-2-ylprop-2-en-1-one
    —— 2-(2-Chloro-4-fluorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]ethanone —— C21H23ClFN2O3+
    2-(2-Chloro-4-fluorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]ethanone
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(3-methyl-5-propan-2-yl-1,2-oxazol-4-yl)methanone —— C21H28N3O3+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(3-methyl-5-propan-2-yl-1,2-oxazol-4-yl)methanone
    —— 3-(3,4-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]propan-1-one —— C22H25F2N2O2S+
    3-(3,4-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]propan-1-one
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(4,6-dimethyl-2-methylsulfanylpyrimidin-5-yl)propan-1-one —— C23H30N4O2S
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(4,6-dimethyl-2-methylsulfanylpyrimidin-5-yl)propan-1-one
    —— 2-[3-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-oxopropyl]-1H-pyridazine-3,6-dione —— C20H25N4O4+
    2-[3-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-oxopropyl]-1H-pyridazine-3,6-dione
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(4-ethyl-5-methylthiophen-2-yl)methanone —— C21H26N2O2S
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(4-ethyl-5-methylthiophen-2-yl)methanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(4-fluorophenyl)propan-1-one —— C22H26FN2O2+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(4-fluorophenyl)propan-1-one
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-4-(4-methoxyphenoxy)butan-1-one —— C24H30N2O4
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-4-(4-methoxyphenoxy)butan-1-one
    —— 4-[(2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-1-oxopropan-2-yl]oxybenzonitrile —— C23H26N3O3+
    4-[(2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-1-oxopropan-2-yl]oxybenzonitrile
    —— (1-Butyl-5-chloro-3-methylpyrazol-4-yl)-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methanone —— C22H29ClN4O2
    (1-Butyl-5-chloro-3-methylpyrazol-4-yl)-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(5-phenylfuran-2-yl)propan-1-one —— C26H28N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(5-phenylfuran-2-yl)propan-1-one
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-ethoxyphenyl)sulfanylethanone —— C23H28N2O3S
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-ethoxyphenyl)sulfanylethanone
    —— 1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(3R)-1,1-dioxothiolan-3-yl]sulfanylethanone —— C19H26N2O4S2
    1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(3R)-1,1-dioxothiolan-3-yl]sulfanylethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-ethoxyphenyl)sulfanylethanone —— C23H29N2O3S+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-ethoxyphenyl)sulfanylethanone
    —— 4-[(2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-1-oxopropan-2-yl]oxybenzonitrile —— C23H26N3O3+
    4-[(2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-1-oxopropan-2-yl]oxybenzonitrile
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(4,6-dimethyl-2-methylsulfanylpyrimidin-5-yl)propan-1-one —— C23H31N4O2S+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(4,6-dimethyl-2-methylsulfanylpyrimidin-5-yl)propan-1-one
    —— 4-[(2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-oxopropan-2-yl]oxybenzonitrile —— C23H25N3O3
    4-[(2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-oxopropan-2-yl]oxybenzonitrile
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-thiophen-3-ylmethanone —— C18H21N2O2S+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-thiophen-3-ylmethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-fluorophenoxy)ethanone —— C21H23FN2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-fluorophenoxy)ethanone
    —— (2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-methylphenyl)sulfanylpropan-1-one —— C23H28N2O2S
    (2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-methylphenyl)sulfanylpropan-1-one
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-[5-(phenoxymethyl)furan-2-yl]methanone —— C25H27N2O4+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-[5-(phenoxymethyl)furan-2-yl]methanone
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(5-ethyl-4-methylthiophen-2-yl)methanone —— C21H27N2O2S+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(5-ethyl-4-methylthiophen-2-yl)methanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[3-(trifluoromethyl)pyrazol-1-yl]ethanone —— C19H21F3N4O2
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[3-(trifluoromethyl)pyrazol-1-yl]ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-methylphenyl)sulfanylethanone —— C22H26N2O2S
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-methylphenyl)sulfanylethanone
    —— (2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-phenylsulfanylpropan-1-one —— C22H26N2O2S
    (2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-phenylsulfanylpropan-1-one
    —— 2-[3-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-oxopropyl]-1H-pyridazine-3,6-dione —— C20H24N4O4
    2-[3-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-oxopropyl]-1H-pyridazine-3,6-dione
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-ethoxyphenoxy)ethanone —— C23H28N2O4
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-ethoxyphenoxy)ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(4-fluorophenyl)propan-1-one —— C22H25FN2O2
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(4-fluorophenyl)propan-1-one
    —— 3-(3,4-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]propan-1-one —— C22H24F2N2O2S
    3-(3,4-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]propan-1-one