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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
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-methyl-1H-1,2,4-triazole —— C15H19N3O2S
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-methyl-1H-1,2,4-triazole
    —— (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methyl-1,3-thiazol-4-yl)prop-2-enamide —— C19H22N2O3S
    (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methyl-1,3-thiazol-4-yl)prop-2-enamide
    —— 1-[5,7-dichloro-2-[2-(2,4-dichlorophenoxy)ethylidene]-3H-1-benzofuran-3-yl]piperidine —— C21H19Cl4NO2
    1-[5,7-dichloro-2-[2-(2,4-dichlorophenoxy)ethylidene]-3H-1-benzofuran-3-yl]piperidine
    —— 5-(2,2-dimethylpropanoylamino)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-methylthiophene-2-carboxamide —— C22H28N2O4S
    5-(2,2-dimethylpropanoylamino)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-methylthiophene-2-carboxamide
    —— (2R)-5-chloro-N-[(R)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H20ClNO2
    (2R)-5-chloro-N-[(R)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[(S)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H20ClNO2
    (2S)-5-chloro-N-[(S)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N-[(S)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H20ClNO2
    (2R)-5-chloro-N-[(S)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 5-(2,2-dimethylpropanoylamino)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-methylthiophene-2-carboxamide —— C22H28N2O4S
    5-(2,2-dimethylpropanoylamino)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-methylthiophene-2-carboxamide
    —— (2S)-5-chloro-N-[(R)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H20ClNO2
    (2S)-5-chloro-N-[(R)-cyclopropyl-(4-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 3-[(4-chlorophenoxy)methyl]-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-methyl-1,2,4-triazole —— C22H24ClN3O3S
    3-[(4-chlorophenoxy)methyl]-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-methyl-1,2,4-triazole
    —— 3-[(4-chlorophenoxy)methyl]-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-methyl-1,2,4-triazole —— C22H24ClN3O3S
    3-[(4-chlorophenoxy)methyl]-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-methyl-1,2,4-triazole
    —— 4-cyclopropyl-3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-propan-2-yl-1,2,4-triazole —— C20H27N3O2S
    4-cyclopropyl-3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-propan-2-yl-1,2,4-triazole
    —— (2R)-5-chloro-N-[[4-(trifluoromethoxy)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H13ClF3NO3
    (2R)-5-chloro-N-[[4-(trifluoromethoxy)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(furan-2-ylmethyl)-5-propan-2-yl-1,2,4-triazole —— C22H27N3O3S
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(furan-2-ylmethyl)-5-propan-2-yl-1,2,4-triazole
    —— (2S)-5-chloro-N-[[4-(trifluoromethoxy)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H13ClF3NO3
    (2S)-5-chloro-N-[[4-(trifluoromethoxy)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[1-(2-methyl-2,3-dihydro-1-benzofuran-6-yl)ethylideneamino]-2-[[5-[1-[2-[1-(2-methyl-2,3-dihydro-1-benzofuran-6-yl)ethylidene]hydrazinyl]-1-oxopropan-2-yl]sulfanyl-1,3,4-thiadiazol-2-yl]sulfanyl]propanamide —— C30H34N6O4S3
    N-[1-(2-methyl-2,3-dihydro-1-benzofuran-6-yl)ethylideneamino]-2-[[5-[1-[2-[1-(2-methyl-2,3-dihydro-1-benzofuran-6-yl)ethylidene]hydrazinyl]-1-oxopropan-2-yl]sulfanyl-1,3,4-thiadiazol-2-yl]sulfanyl]propanamide
    —— [(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone —— C25H29NO5
    [(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone
    —— [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone —— C25H29NO5
    [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone
    —— 3-[2-(3-fluorophenyl)ethyl-octanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H43FN2O7
    3-[2-(3-fluorophenyl)ethyl-octanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[acetyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C23H30N2O7
    3-[acetyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone —— C25H29NO5
    [(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone
    —— 3-[2-(3-fluorophenyl)ethyl-(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H37FN2O7
    3-[2-(3-fluorophenyl)ethyl-(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-[Cyclopropyl(2,3-dihydro-1-benzofuran-5-ylmethyl)amino]-4-oxobutanoic acid —— C16H19NO4
    4-[Cyclopropyl(2,3-dihydro-1-benzofuran-5-ylmethyl)amino]-4-oxobutanoic acid
    —— 4-[4-[(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide —— C21H26N4O5S
    4-[4-[(2R,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide
    —— 8-formyl-3-[hexyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H38N2O8
    8-formyl-3-[hexyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-[4-[(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide —— C21H26N4O5S
    4-[4-[(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide
    —— 4-[4-[(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide —— C21H26N4O5S
    4-[4-[(2S,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide
    —— 4-[4-[(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide —— C21H26N4O5S
    4-[4-[(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carbonyl]piperazin-1-yl]sulfonyl-1-methylpyrrole-2-carboxamide
    —— 5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-N-ethyl-1,3,4-thiadiazol-2-amine —— C16H21N3O2S2
    5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-N-ethyl-1,3,4-thiadiazol-2-amine
    —— 3-[5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(2-methylpropyl)-1,2,4-triazol-3-yl]propanamide —— C21H30N4O3S
    3-[5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(2-methylpropyl)-1,2,4-triazol-3-yl]propanamide
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-propyl-1H-1,2,4-triazol-5-one —— C17H23N3O3S
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-propyl-1H-1,2,4-triazol-5-one
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-propyl-1H-1,2,4-triazol-5-one —— C17H23N3O3S
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-propyl-1H-1,2,4-triazol-5-one
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2R)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole —— C23H27N3O3S2
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2R)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole
    —— 4-[4-benzyl-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-3-yl]morpholine —— C25H30N4O3S
    4-[4-benzyl-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-3-yl]morpholine
    —— [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 3-(3,4,5-trimethoxyphenyl)propanoate —— C24H30O7
    [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 3-(3,4,5-trimethoxyphenyl)propanoate
    —— 2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(furan-2-yl)-1,3,4-oxadiazole —— C18H18N2O4S
    2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(furan-2-yl)-1,3,4-oxadiazole
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2R)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole —— C23H27N3O3S2
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2R)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole
    —— 5-acetyl-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-6-methylpyridine-3-carbonitrile —— C21H22N2O3S
    5-acetyl-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-6-methylpyridine-3-carbonitrile
    —— 2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(furan-2-yl)-1,3,4-oxadiazole —— C18H18N2O4S
    2-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(furan-2-yl)-1,3,4-oxadiazole
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2S)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole —— C23H27N3O3S2
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-[[(2S)-oxolan-2-yl]methyl]-5-thiophen-2-yl-1,2,4-triazole
    —— 3-[5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(2-methylpropyl)-1,2,4-triazol-3-yl]propanamide —— C21H30N4O3S
    3-[5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-4-(2-methylpropyl)-1,2,4-triazol-3-yl]propanamide
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(trifluoromethyl)-1,2,4-triazol-4-amine —— C15H17F3N4O2S
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(trifluoromethyl)-1,2,4-triazol-4-amine
    —— 3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(2-methylfuran-3-yl)-4-prop-2-enyl-1,2,4-triazole —— C22H25N3O3S
    3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(2-methylfuran-3-yl)-4-prop-2-enyl-1,2,4-triazole
    —— [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(4-methoxyphenyl)acetate —— C21H24O5
    [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(4-methoxyphenyl)acetate
    —— [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(4-methoxyphenyl)acetate —— C21H24O5
    [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 2-(4-methoxyphenyl)acetate
    —— [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 3-(3,4,5-trimethoxyphenyl)propanoate —— C24H30O7
    [(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl 3-(3,4,5-trimethoxyphenyl)propanoate
    —— 3-cyclopropyl-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-4-amine —— C17H22N4O2S
    3-cyclopropyl-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,2,4-triazol-4-amine
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(trifluoromethyl)-1,2,4-triazol-4-amine —— C15H17F3N4O2S
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-5-(trifluoromethyl)-1,2,4-triazol-4-amine
    —— [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl (E)-3-(furan-2-yl)prop-2-enoate —— C19H20O5
    [(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl (E)-3-(furan-2-yl)prop-2-enoate
    —— 2-(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]acetamide —— C23H26ClNO5
    2-(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]acetamide