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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
    —— (2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxamide —— C12H13NO2
    (2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxamide
    —— 6-Ethyl-2,3-dihydro-1-benzofuran-7-ol —— C10H12O2
    6-Ethyl-2,3-dihydro-1-benzofuran-7-ol
    —— 7-(1,1-difluoroethoxymethyl)-2,2-dimethyl-3H-1-benzofuran —— C13H16F2O2
    7-(1,1-difluoroethoxymethyl)-2,2-dimethyl-3H-1-benzofuran
    —— fluoro 2-[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate —— C10H9FO4
    fluoro 2-[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate
    —— methyl 2-[(3S)-6-[(1R,3E,5E)-6-(4-bromophenoxy)-3-fluoro-7-methylidenecyclonona-3,5-dien-1-yl]oxy-2,3-dihydro-1-benzofuran-3-yl]acetate —— C27H26BrFO5
    methyl 2-[(3S)-6-[(1R,3E,5E)-6-(4-bromophenoxy)-3-fluoro-7-methylidenecyclonona-3,5-dien-1-yl]oxy-2,3-dihydro-1-benzofuran-3-yl]acetate
    —— 4-[(1R,3aS,8bS)-1-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-[(1S,2R)-2-(6-sulfanylhexylcarbamoyl)cyclohexanecarbonyl]oxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoic acid —— C38H53NO7S
    4-[(1R,3aS,8bS)-1-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-[(1S,2R)-2-(6-sulfanylhexylcarbamoyl)cyclohexanecarbonyl]oxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoic acid
    —— 4-[(1R,3aS,8bS)-1-[(E,3S)-4-methyl-3-trimethylsilyloxyoct-1-en-6-ynyl]-2-trimethylsilyloxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoic acid —— C30H46O5Si2
    4-[(1R,3aS,8bS)-1-[(E,3S)-4-methyl-3-trimethylsilyloxyoct-1-en-6-ynyl]-2-trimethylsilyloxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoic acid
    —— 4-[(1R,3aS,8bS)-1-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-[2-(6-sulfanylhexylcarbamoyl)cyclohexanecarbonyl]oxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoic acid —— C38H53NO7S
    4-[(1R,3aS,8bS)-1-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2-[2-(6-sulfanylhexylcarbamoyl)cyclohexanecarbonyl]oxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoic acid
    —— (2Z,3S)-2-[(3-ethoxy-4-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol —— C24H22O4
    (2Z,3S)-2-[(3-ethoxy-4-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol
    —— (2Z,3R)-2-[(3-ethoxy-4-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol —— C24H22O4
    (2Z,3R)-2-[(3-ethoxy-4-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol
    —— (2E,3S)-2-[(3-ethoxy-4-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol —— C24H22O4
    (2E,3S)-2-[(3-ethoxy-4-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol
    —— 2-formyl-N-(1-methylpyrazol-3-yl)-4-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-6-carboxamide —— C23H23N3O3
    2-formyl-N-(1-methylpyrazol-3-yl)-4-(3-phenylpropyl)-2,3-dihydro-1-benzofuran-6-carboxamide
    —— 7-bromo-4-[(Z)-1-methoxyprop-1-enyl]-2,2-dimethyl-3H-1-benzofuran-6-ol —— C14H17BrO3
    7-bromo-4-[(Z)-1-methoxyprop-1-enyl]-2,2-dimethyl-3H-1-benzofuran-6-ol
    —— N-(2-ethyltriazol-4-yl)-2,2,4-trimethyl-3H-1-benzofuran-6-carboxamide —— C16H20N4O2
    N-(2-ethyltriazol-4-yl)-2,2,4-trimethyl-3H-1-benzofuran-6-carboxamide
    —— methyl 4-[(3E,5E)-6-cyanohepta-1,3,5-trien-3-yl]oxy-2,2-dimethyl-3H-1-benzofuran-6-carboxylate —— C20H21NO4
    methyl 4-[(3E,5E)-6-cyanohepta-1,3,5-trien-3-yl]oxy-2,2-dimethyl-3H-1-benzofuran-6-carboxylate
    —— 6-(1-methoxyethenyl)-2,2-dimethyl-3H-1-benzofuran-4-ol —— C13H16O3
    6-(1-methoxyethenyl)-2,2-dimethyl-3H-1-benzofuran-4-ol
    —— 2-(difluoromethyl)-4-methyl-N-(1-methylpyrazol-3-yl)-2,3-dihydro-1-benzofuran-6-carboxamide —— C15H15F2N3O2
    2-(difluoromethyl)-4-methyl-N-(1-methylpyrazol-3-yl)-2,3-dihydro-1-benzofuran-6-carboxamide
    —— 1-[2-(2,3-Dihydro-1-benzofuran-7-carbonylamino)ethyl]triazole-4-carboxylic acid —— C14H14N4O4
    1-[2-(2,3-Dihydro-1-benzofuran-7-carbonylamino)ethyl]triazole-4-carboxylic acid
    —— 6,9-Dimethyl-1,2,3,4,4a,9b-hexahydrodibenzofuran —— C14H18O
    6,9-Dimethyl-1,2,3,4,4a,9b-hexahydrodibenzofuran
    —— 1-[5-[7-Chloro-2-[(chloroamino)methyl]-2,3-dihydro-1-benzofuran-5-yl]thiophen-2-yl]ethanone —— C15H13Cl2NO2S
    1-[5-[7-Chloro-2-[(chloroamino)methyl]-2,3-dihydro-1-benzofuran-5-yl]thiophen-2-yl]ethanone
    —— (5-Bromo-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl methanesulfonate —— C11H13BrO4S
    (5-Bromo-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl methanesulfonate
    —— (E)-N-[[7-(5-acetylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-aminopyridin-3-yl)prop-2-enamide —— C23H21N3O3S
    (E)-N-[[7-(5-acetylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-aminopyridin-3-yl)prop-2-enamide
    —— 5-[2-[[[(E)-3-(6-aminopyridin-3-yl)prop-2-enoyl]amino]methyl]-7-chloro-2,3-dihydro-1-benzofuran-5-yl]-N,N-dimethylfuran-2-carboxamide —— C24H23ClN4O4
    5-[2-[[[(E)-3-(6-aminopyridin-3-yl)prop-2-enoyl]amino]methyl]-7-chloro-2,3-dihydro-1-benzofuran-5-yl]-N,N-dimethylfuran-2-carboxamide
    —— [7-Chloro-5-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H16ClNO
    [7-Chloro-5-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— tert-butyl N-[[7-(5-acetylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate —— C20H23NO4S
    tert-butyl N-[[7-(5-acetylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate
    —— (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[2,5-dimethyl-1-(1,3-thiazol-2-yl)pyrrol-3-yl]prop-2-enamide —— C27H24ClN3O3S2
    (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[2,5-dimethyl-1-(1,3-thiazol-2-yl)pyrrol-3-yl]prop-2-enamide
    —— 1-[5-[2-(Aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]thiophen-2-yl]ethanone —— C15H15NO2S
    1-[5-[2-(Aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]thiophen-2-yl]ethanone
    —— tert-butyl N-[[7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate —— C20H21ClFNO3
    tert-butyl N-[[7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate
    —— tert-butyl N-[[7-chloro-5-(3,5-dimethyl-1,2-oxazol-4-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate —— C19H23ClN2O4
    tert-butyl N-[[7-chloro-5-(3,5-dimethyl-1,2-oxazol-4-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate
    —— [7-Chloro-5-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C15H13ClFNO
    [7-Chloro-5-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— (E)-ethyl 3-(4-bromo-7-chloro-2,3-dihydrobenzofuran-2-yl)acrylate —— C13H12BrClO3
    (E)-ethyl 3-(4-bromo-7-chloro-2,3-dihydrobenzofuran-2-yl)acrylate
    —— (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1-methylpyrazol-4-yl)prop-2-enamide —— C22H20ClN3O3S
    (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1-methylpyrazol-4-yl)prop-2-enamide
    —— [7-Chloro-5-(furan-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C13H12ClNO2
    [7-Chloro-5-(furan-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— tert-butyl N-[(7-chloro-5-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl]carbamate —— C20H22ClNO3
    tert-butyl N-[(7-chloro-5-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl]carbamate
    —— (E)-N-[(5-bromo-7-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-pyridin-3-ylprop-2-enamide —— C17H14BrClN2O2
    (E)-N-[(5-bromo-7-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-pyridin-3-ylprop-2-enamide
    —— tert-butyl N-[[7-chloro-5-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate —— C21H24ClNO3
    tert-butyl N-[[7-chloro-5-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate
    —— tert-butyl N-[(7-chloro-5-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl]carbamate —— C19H21ClN2O3
    tert-butyl N-[(7-chloro-5-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl]carbamate
    —— (5-Bromo-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methanol —— C10H11BrO2
    (5-Bromo-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methanol
    —— 1-[5-(7-Chloro-2,3-dihydro-1-benzofuran-5-yl)thiophen-2-yl]ethanone —— C14H11ClO2S
    1-[5-(7-Chloro-2,3-dihydro-1-benzofuran-5-yl)thiophen-2-yl]ethanone
    —— (E)-N-[(5-bromo-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-pyridin-3-ylprop-2-enamide —— C18H17BrN2O2
    (E)-N-[(5-bromo-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-pyridin-3-ylprop-2-enamide
    —— (E)-N-[[5-(5-acetylfuran-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-aminopyridin-3-yl)prop-2-enamide —— C23H20ClN3O4
    (E)-N-[[5-(5-acetylfuran-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(6-aminopyridin-3-yl)prop-2-enamide
    —— tert-butyl (7-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzofuran-2-yl)methylcarbamate —— C20H29BClNO5
    tert-butyl (7-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzofuran-2-yl)methylcarbamate
    —— (Z)-N-((5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydrobenzofuran-2-yl)methyl)-3-(pyridin-3-yl)acrylamide —— C23H19ClN2O3S
    (Z)-N-((5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydrobenzofuran-2-yl)methyl)-3-(pyridin-3-yl)acrylamide
    —— (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2-tert-butyl-1,3-thiazol-5-yl)prop-2-enamide —— C25H25ClN2O3S2
    (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(2-tert-butyl-1,3-thiazol-5-yl)prop-2-enamide
    —— tert-butyl N-[[7-chloro-5-(5-methylsulfonylpyridin-3-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate —— C20H23ClN2O5S
    tert-butyl N-[[7-chloro-5-(5-methylsulfonylpyridin-3-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate
    —— N-((5-(5-Acetylthiophen-2-yl)-7-chloro-2,3-dihydrobenzofuran-2-yl)methyl)-3-(6-aminopyridin-3-yl)propanamide —— C23H22ClN3O3S
    N-((5-(5-Acetylthiophen-2-yl)-7-chloro-2,3-dihydrobenzofuran-2-yl)methyl)-3-(6-aminopyridin-3-yl)propanamide
    —— (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-cyano-3-(furan-3-yl)prop-2-enamide —— C23H17ClN2O4S
    (E)-N-[[5-(5-acetylthiophen-2-yl)-7-chloro-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-cyano-3-(furan-3-yl)prop-2-enamide
    —— 1-[5-[7-Chloro-2-(methylaminomethyl)-2,3-dihydro-1-benzofuran-5-yl]-3,4-dimethylthiophen-2-yl]ethanone —— C18H20ClNO2S
    1-[5-[7-Chloro-2-(methylaminomethyl)-2,3-dihydro-1-benzofuran-5-yl]-3,4-dimethylthiophen-2-yl]ethanone
    —— (E)-N-[(4-bromo-7-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-pyridin-3-ylprop-2-enamide —— C17H14BrClN2O2
    (E)-N-[(4-bromo-7-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-pyridin-3-ylprop-2-enamide
    —— ethyl (E)-3-[7-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-yl]prop-2-enoate —— C19H24BClO5
    ethyl (E)-3-[7-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-yl]prop-2-enoate