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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
    —— (2R)-5-chloro-N-[[4-(dimethylamino)phenyl]methyl]-N-[[(2S)-oxolan-2-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C23H27ClN2O3
    (2R)-5-chloro-N-[[4-(dimethylamino)phenyl]methyl]-N-[[(2S)-oxolan-2-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[[4-(dimethylamino)phenyl]methyl]-N-[[(2S)-oxolan-2-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C23H27ClN2O3
    (2S)-5-chloro-N-[[4-(dimethylamino)phenyl]methyl]-N-[[(2S)-oxolan-2-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2R)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C26H30N2O4
    (2R)-N-[(2R)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(2S)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C26H30N2O4
    (2S)-N-[(2S)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2S)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C26H30N2O4
    (2R)-N-[(2S)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(2R)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C26H30N2O4
    (2S)-N-[(2R)-2-cyclohexyl-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(2S)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C24H28N2O4
    (2S)-N-[(2S)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2S)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C24H28N2O4
    (2R)-N-[(2S)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(2R)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C24H28N2O4
    (2S)-N-[(2R)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2R)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C24H28N2O4
    (2R)-N-[(2R)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-4-methylpentyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-ethyl-1,2,4-oxadiazol-3-yl)methyl]piperazin-1-yl]methanone —— C18H22N4O3
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-ethyl-1,2,4-oxadiazol-3-yl)methyl]piperazin-1-yl]methanone
    —— (2R)-N-[2-[3-(furan-2-yl)-1H-1,2,4-triazol-5-yl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16N4O3
    (2R)-N-[2-[3-(furan-2-yl)-1H-1,2,4-triazol-5-yl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-ethyl-1,2,4-oxadiazol-3-yl)methyl]piperazin-1-yl]methanone —— C18H22N4O3
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(5-ethyl-1,2,4-oxadiazol-3-yl)methyl]piperazin-1-yl]methanone
    —— (2S)-N-[2-[3-(furan-2-yl)-1H-1,2,4-triazol-5-yl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16N4O3
    (2S)-N-[2-[3-(furan-2-yl)-1H-1,2,4-triazol-5-yl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-3-(methoxymethyl)-1,2,4-oxadiazole —— C12H12N2O3
    5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-3-(methoxymethyl)-1,2,4-oxadiazole
    —— 5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-3-(methoxymethyl)-1,2,4-oxadiazole —— C12H12N2O3
    5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-3-(methoxymethyl)-1,2,4-oxadiazole
    —— [(2S)-oxan-2-yl]methyl (2R,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O4
    [(2S)-oxan-2-yl]methyl (2R,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— [(2S)-oxan-2-yl]methyl (2S,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O4
    [(2S)-oxan-2-yl]methyl (2S,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— cyclohexyl (2S,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O3
    cyclohexyl (2S,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— cyclohexyl (2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O3
    cyclohexyl (2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— cyclohexyl (2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O3
    cyclohexyl (2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— cyclohexyl (2R,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O3
    cyclohexyl (2R,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— [(2S)-oxan-2-yl]methyl (2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O4
    [(2S)-oxan-2-yl]methyl (2S,3S)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— [(2S)-oxan-2-yl]methyl (2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate —— C16H20O4
    [(2S)-oxan-2-yl]methyl (2R,3R)-3-methyl-2,3-dihydro-1-benzofuran-2-carboxylate
    —— tert-butyl N-[(2R)-2-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate —— C20H30N2O4
    tert-butyl N-[(2R)-2-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate
    —— tert-butyl N-[(2S)-2-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate —— C20H30N2O4
    tert-butyl N-[(2S)-2-[[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate
    —— tert-butyl N-[(2S)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate —— C20H30N2O4
    tert-butyl N-[(2S)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate
    —— tert-butyl N-[(2R)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate —— C20H30N2O4
    tert-butyl N-[(2R)-2-[[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]amino]-2,3-dimethylbutyl]carbamate
    —— (3R)-N-[(2R)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H24N2O2S
    (3R)-N-[(2R)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(5-thiophen-3-yltetrazol-2-yl)acetamide —— C19H21N5O3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(5-thiophen-3-yltetrazol-2-yl)acetamide
    —— (3S)-N-[(2R)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H24N2O2S
    (3S)-N-[(2R)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-(4-fluorophenyl)-4-methyl-1,2-oxazole —— C24H28FN3O2+2
    3-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-(4-fluorophenyl)-4-methyl-1,2-oxazole
    —— 2-[[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]methyl]-7-methyl-8H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-4-ium-5-one —— C20H25N5O2S+2
    2-[[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]methyl]-7-methyl-8H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-4-ium-5-one
    —— (3S)-N-[(2R)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H23ClN2O2
    (3S)-N-[(2R)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-[1-[(2S)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]ethanone —— C25H35N3O3
    2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-[1-[(2S)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]ethanone
    —— 2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethyl]-5-thiophen-2-yl-1,3,4-oxadiazole —— C21H26N4O2S+2
    2-[(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]ethyl]-5-thiophen-2-yl-1,3,4-oxadiazole
    —— 2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazole —— C22H28N4O3+2
    2-[[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-(2,5-dimethylfuran-3-yl)-1,3,4-oxadiazole
    —— (3R)-N-(2-propan-2-ylpyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H17N3O2
    (3R)-N-(2-propan-2-ylpyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-[1-[(2R)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]ethanone —— C25H37N3O3+2
    2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]-1-[1-[(2R)-1-methoxypropan-2-yl]-2,5-dimethylpyrrol-3-yl]ethanone
    —— (3R)-N-[4-[(4-methylpiperidin-1-yl)methyl]-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H23N3O2S
    (3R)-N-[4-[(4-methylpiperidin-1-yl)methyl]-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2R)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H24N2O2
    (3R)-N-[(2R)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— ethyl N-[[(3R)-2,3-dihydro-1-benzofuran-3-carbonyl]amino]carbamate —— C12H14N2O4
    ethyl N-[[(3R)-2,3-dihydro-1-benzofuran-3-carbonyl]amino]carbamate
    —— (3R)-N-[(2S)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H24N2O2S
    (3R)-N-[(2S)-2-(diethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[3-(4-ethylpiperazin-1-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H27N3O2
    (3S)-N-[3-(4-ethylpiperazin-1-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— ethyl N-[[(3S)-2,3-dihydro-1-benzofuran-3-carbonyl]amino]carbamate —— C12H14N2O4
    ethyl N-[[(3S)-2,3-dihydro-1-benzofuran-3-carbonyl]amino]carbamate
    —— (3S)-N-[(2S)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H24N2O2
    (3S)-N-[(2S)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-(2-propan-2-ylpyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H17N3O2
    (3S)-N-(2-propan-2-ylpyrazol-3-yl)-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2S)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H24N2O2
    (3R)-N-[(2S)-1-piperidin-1-ylpropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[4-[(4-methylpiperidin-1-yl)methyl]-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C19H23N3O2S
    (3S)-N-[4-[(4-methylpiperidin-1-yl)methyl]-1,3-thiazol-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2S)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C21H23ClN2O2
    (3R)-N-[(2S)-2-(3-chlorophenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide