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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-[(2S)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]ethyl-dimethylazanium —— C23H27N2O5+
    2-[(2S)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]ethyl-dimethylazanium
    —— [(2R)-1-[2-(dimethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate —— C23H26N2O5
    [(2R)-1-[2-(dimethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate
    —— [(2S)-1-[2-(dimethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate —— C23H26N2O5
    [(2S)-1-[2-(dimethylazaniumyl)ethyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanolate
    —— 2-[(2R)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]ethyl-dimethylazanium —— C23H27N2O5+
    2-[(2R)-3-[hydroxy-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]ethyl-dimethylazanium
    —— 2-[(2R)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]ethyl-dimethylazanium —— C23H27N2O5+
    2-[(2R)-3-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-1-yl]ethyl-dimethylazanium
    —— (3R)-4,7-Difluoro-2,3-dihydro-1-benzofuran-3-amine —— C8H7F2NO
    (3R)-4,7-Difluoro-2,3-dihydro-1-benzofuran-3-amine
    —— (3S)-4,7-Difluoro-2,3-dihydrobenzo[B]furan-3-ylamine —— C8H7F2NO
    (3S)-4,7-Difluoro-2,3-dihydrobenzo[B]furan-3-ylamine
    —— (5E)-3-[(3R)-1,1-dioxothiolan-3-yl]-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H17NO4S3
    (5E)-3-[(3R)-1,1-dioxothiolan-3-yl]-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (5E)-3-[(3S)-1,1-dioxothiolan-3-yl]-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H17NO4S3
    (5E)-3-[(3S)-1,1-dioxothiolan-3-yl]-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— (3S)-3-(2,3-dihydro-1-benzofuran-5-ylmethyl)pyrrolidine —— C13H17NO
    (3S)-3-(2,3-dihydro-1-benzofuran-5-ylmethyl)pyrrolidine
    —— (3R)-3-(2,3-dihydro-1-benzofuran-5-ylmethyl)pyrrolidine —— C13H17NO
    (3R)-3-(2,3-dihydro-1-benzofuran-5-ylmethyl)pyrrolidine
    —— (2R)-6-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylic acid —— C9H8O4
    (2R)-6-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylic acid
    —— (2S)-6-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylic acid —— C9H8O4
    (2S)-6-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylic acid
    —— (3R)-N-[(2S)-1-cyanopropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C13H14N2O2
    (3R)-N-[(2S)-1-cyanopropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(5-methyl-1H-pyrazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H15N3O2
    (3S)-N-[(5-methyl-1H-pyrazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(2R)-1-cyanopropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C13H14N2O2
    (3R)-N-[(2R)-1-cyanopropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[(2R)-1-cyanopropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C13H14N2O2
    (3S)-N-[(2R)-1-cyanopropan-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 2-ethoxy-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide —— C15H21NO4
    2-ethoxy-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide
    —— 2-ethoxy-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide —— C15H21NO4
    2-ethoxy-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]acetamide
    —— (3R)-N-[(5-methyl-1H-pyrazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C14H15N3O2
    (3R)-N-[(5-methyl-1H-pyrazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]propane-1-sulfonamide —— C11H15NO3S
    N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]propane-1-sulfonamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]propanamide —— C12H15NO2
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]propanamide
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-morpholin-4-ylmethanone —— C13H15NO3
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-morpholin-4-ylmethanone
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-morpholin-4-ylmethanone —— C13H15NO3
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-morpholin-4-ylmethanone
    —— N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-5-nitroimidazo[2,1-b][1,3]thiazol-6-amine —— C13H10N4O3S
    N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-5-nitroimidazo[2,1-b][1,3]thiazol-6-amine
    —— (2S)-5-chloro-N-(1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C12H10ClN3O2
    (2S)-5-chloro-N-(1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-(1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C12H10ClN3O2
    (2R)-5-chloro-N-(1H-imidazol-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3R)-6-[(3R)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine —— C15H21NO3
    (3R)-6-[(3R)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine
    —— (3S)-6-[(3S)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine —— C15H21NO3
    (3S)-6-[(3S)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine
    —— (3R)-6-[(3S)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine —— C15H21NO3
    (3R)-6-[(3S)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine
    —— (3S)-6-[(3R)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine —— C15H21NO3
    (3S)-6-[(3R)-oxolan-3-yl]oxy-N-propyl-2,3-dihydro-1-benzofuran-3-amine
    —— N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-pyrazol-1-ylethanamine —— C16H21N3O2
    N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-pyrazol-1-ylethanamine
    —— N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-pyrazol-1-ylethanamine —— C16H21N3O2
    N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-pyrazol-1-ylethanamine
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-[(4-methylpyrazol-1-yl)methyl]pyrrolidin-1-yl]ethanone —— C19H23N3O2
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2S)-2-[(4-methylpyrazol-1-yl)methyl]pyrrolidin-1-yl]ethanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-[(4-methylpyrazol-1-yl)methyl]pyrrolidin-1-yl]ethanone —— C19H23N3O2
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[(2R)-2-[(4-methylpyrazol-1-yl)methyl]pyrrolidin-1-yl]ethanone
    —— (3S)-N-[2-oxo-5-(trifluoromethyl)-1H-pyridin-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H11F3N2O3
    (3S)-N-[2-oxo-5-(trifluoromethyl)-1H-pyridin-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[2-oxo-5-(trifluoromethyl)-1H-pyridin-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H11F3N2O3
    (3R)-N-[2-oxo-5-(trifluoromethyl)-1H-pyridin-3-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3S)-N-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H22N4O3
    (3S)-N-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C18H22N4O3
    (3R)-N-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(pyrazol-1-ylmethyl)pyrrolidin-1-yl]methanone —— C17H19N3O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(pyrazol-1-ylmethyl)pyrrolidin-1-yl]methanone
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(pyrazol-1-ylmethyl)pyrrolidin-1-yl]methanone —— C17H19N3O2
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[(2S)-2-(pyrazol-1-ylmethyl)pyrrolidin-1-yl]methanone
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(pyrazol-1-ylmethyl)pyrrolidin-1-yl]methanone —— C17H19N3O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-(pyrazol-1-ylmethyl)pyrrolidin-1-yl]methanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[4-[(2S)-2-hydroxybutyl]piperazin-1-yl]ethanone —— C18H26N2O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[4-[(2S)-2-hydroxybutyl]piperazin-1-yl]ethanone
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-1-[4-[(2R)-2-hydroxybutyl]piperazin-1-yl]ethanone —— C18H26N2O3
    2-(2,3-dihydro-1-benzofuran-5-yl)-1-[4-[(2R)-2-hydroxybutyl]piperazin-1-yl]ethanone
    —— N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]azepane-1-sulfonamide —— C16H24N2O3S
    N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]azepane-1-sulfonamide
    —— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-(3-phenylprop-2-ynyl)urea —— C18H16N2O2
    1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-(3-phenylprop-2-ynyl)urea
    —— [(5S)-3-(2,3-dihydro-1-benzofuran-5-yl)-4,5-dihydro-1,2-oxazol-5-yl]methanamine —— C12H14N2O2
    [(5S)-3-(2,3-dihydro-1-benzofuran-5-yl)-4,5-dihydro-1,2-oxazol-5-yl]methanamine
    —— 1-[(2R)-4-ethylmorpholin-2-yl]-N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]methanamine —— C18H28N2O3
    1-[(2R)-4-ethylmorpholin-2-yl]-N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]methanamine
    —— 1-[4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]piperazin-1-yl]ethanone —— C18H26N2O3
    1-[4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]piperazin-1-yl]ethanone
    —— 1-[(2S)-4-ethylmorpholin-2-yl]-N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]methanamine —— C18H28N2O3
    1-[(2S)-4-ethylmorpholin-2-yl]-N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]methanamine