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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
    —— 1-(6-chloro-3,4-dihydro-2H-1,5-benzodioxepin-8-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine —— C22H26ClNO4
    1-(6-chloro-3,4-dihydro-2H-1,5-benzodioxepin-8-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]methanamine
    —— 2,3,5,6-Tetrahydrofuro[3,2-f][1]benzofuran-8-amine —— C10H11NO2
    2,3,5,6-Tetrahydrofuro[3,2-f][1]benzofuran-8-amine
    —— (2S)-5-chloro-N-[(2R)-2-phenylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H18ClNO2
    (2S)-5-chloro-N-[(2R)-2-phenylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[2-(4-methylphenoxy)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H18ClNO3
    (2R)-5-chloro-N-[2-(4-methylphenoxy)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[(3-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H16ClNO3
    (2S)-5-chloro-N-[(3-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[2-(3,4-diethoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H24ClNO4
    (2S)-5-chloro-N-[2-(3,4-diethoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]azanium —— C24H34N2O3+2
    [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]azanium
    —— [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]azanium —— C24H34N2O3+2
    [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl-[[2-(morpholin-4-ium-4-ylmethyl)phenyl]methyl]azanium
    —— [(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone —— C19H22N2O4S2
    [(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone
    —— [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone —— C19H22N2O4S2
    [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone
    —— N-(5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-2-yl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C18H20N2O3S
    N-(5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-2-yl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-2-(3,5-dimethylpyrazol-1-yl)acetohydrazide —— C19H24N4O4
    N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-2-(3,5-dimethylpyrazol-1-yl)acetohydrazide
    —— 1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea —— C18H25N3O3S
    1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-[[(2R)-oxolan-2-yl]methyl]thiourea
    —— 1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea —— C18H25N3O3S
    1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-[[(2S)-oxolan-2-yl]methyl]thiourea
    —— (2R)-5-chloro-N-[2-(4-chlorophenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H15Cl2NO2
    (2R)-5-chloro-N-[2-(4-chlorophenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H15ClFNO2
    (2R)-5-chloro-N-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[(3-chlorophenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H13Cl2NO2
    (2S)-5-chloro-N-[(3-chlorophenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 6-(carbamoylamino)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]hexanamide —— C19H29N3O4
    6-(carbamoylamino)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]hexanamide
    —— 2-[(3R)-1,1-dioxothiolan-3-yl]sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H25NO5S2
    2-[(3R)-1,1-dioxothiolan-3-yl]sulfanyl-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]-1-methylpyrazole-4-carboxamide —— C17H21N3O3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methylpyrazole-4-carboxamide
    —— 3-(4,6-dimethyl-2-methylsulfanylpyrimidin-5-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C22H29N3O3S
    3-(4,6-dimethyl-2-methylsulfanylpyrimidin-5-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide
    —— 1-benzyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]pyrazole-4-carboxamide —— C23H25N3O3
    1-benzyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]pyrazole-4-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methylpyrazole-4-carboxamide —— C17H21N3O3
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-methylpyrazole-4-carboxamide
    —— 2-[(3S)-1,1-dioxothiolan-3-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H25NO5S
    2-[(3S)-1,1-dioxothiolan-3-yl]-N-[[(2R)-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]thiophene-3-carboxamide —— C17H19NO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-3-carboxamide
    —— 2-[(3R)-1,1-dioxothiolan-3-yl]sulfanyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H25NO5S2
    2-[(3R)-1,1-dioxothiolan-3-yl]sulfanyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— (2S)-5-chloro-N-[(2-chlorophenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H13Cl2NO2
    (2S)-5-chloro-N-[(2-chlorophenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-3-carboxamide —— C17H19NO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-3-carboxamide
    —— ethyl 1-[2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl]-2,5-dimethylpyrrole-3-carboxylate —— C23H30N2O5
    ethyl 1-[2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl]-2,5-dimethylpyrrole-3-carboxylate
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-fluorophenyl)propanamide —— C21H24FNO3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-fluorophenyl)propanamide
    —— ethyl 1-[2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl]-2,5-dimethylpyrrole-3-carboxylate —— C23H30N2O5
    ethyl 1-[2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-2-oxoethyl]-2,5-dimethylpyrrole-3-carboxylate
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-methoxyphenyl)sulfanylacetamide —— C21H25NO4S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-methoxyphenyl)sulfanylacetamide
    —— 2-(2,5-difluorophenyl)sulfanyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H21F2NO3S
    2-(2,5-difluorophenyl)sulfanyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-methoxyphenyl)sulfanylacetamide —— C21H25NO4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-methoxyphenyl)sulfanylacetamide
    —— (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-methylthiophen-2-yl)prop-2-enamide —— C20H23NO3S
    (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-methylthiophen-2-yl)prop-2-enamide
    —— (2S)-2-(4-cyanophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C22H24N2O4
    (2S)-2-(4-cyanophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(4-methoxyphenoxy)butanamide —— C23H29NO5
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(4-methoxyphenoxy)butanamide
    —— (E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-methylthiophen-2-yl)prop-2-enamide —— C20H23NO3S
    (E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-methylthiophen-2-yl)prop-2-enamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]sulfanylacetamide —— C20H25N3O5S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]sulfanylacetamide
    —— 2-(2-chloro-4-fluorophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H21ClFNO4
    2-(2-chloro-4-fluorophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-(2-chloro-4-fluorophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H21ClFNO4
    2-(2-chloro-4-fluorophenoxy)-N-[[(2R)-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]-4-thiophen-2-ylbutanamide —— C20H25NO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-thiophen-2-ylbutanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)acetamide —— C20H22FNO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-fluorophenyl)sulfanylpropanamide —— C21H24FNO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-fluorophenyl)sulfanylpropanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-formyl-2-methoxyphenoxy)acetamide —— C22H25NO6
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-formyl-2-methoxyphenoxy)acetamide
    —— 2-(3-chlorophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H22ClNO4
    2-(3-chlorophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-fluorophenyl)sulfanylpropanamide —— C21H24FNO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(4-fluorophenyl)sulfanylpropanamide
    —— 2-(2,6-dimethylphenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C22H27NO4
    2-(2,6-dimethylphenoxy)-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]-3-(2-methoxyphenyl)propanamide —— C22H27NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methoxyphenyl)propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methoxyphenyl)propanamide —— C22H27NO4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methoxyphenyl)propanamide