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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
    —— methyl (1R,2S,3R,7E,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C27H19ClN2O5S
    methyl (1R,2S,3R,7E,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
    —— methyl (1R,2S,3R,7E,10R)-7-[[5-(3-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C27H19ClN2O5S
    methyl (1R,2S,3R,7E,10R)-7-[[5-(3-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
    —— methyl (1R,2S,3R,7E,10R)-7-[(3,5-dichloro-2-hydroxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C23H16Cl2N2O5S
    methyl (1R,2S,3R,7E,10R)-7-[(3,5-dichloro-2-hydroxyphenyl)methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
    —— methyl (1R,2S,3R,7E,10R)-7-[[5-(4-bromophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C27H19BrN2O5S
    methyl (1R,2S,3R,7E,10R)-7-[[5-(4-bromophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
    —— methyl (1R,2S,3S,7E,10R)-7-[[5-(4-bromophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C27H19BrN2O5S
    methyl (1R,2S,3S,7E,10R)-7-[[5-(4-bromophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
    —— (5R,7R)-3-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]adamantane-1-carboxamide —— C23H30BrNO3
    (5R,7R)-3-bromo-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]adamantane-1-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(ethylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide —— C18H24N4O3S2
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[[5-(ethylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]acetamide
    —— (2S)-N-[[4-(dimethylamino)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H20N2O2
    (2S)-N-[[4-(dimethylamino)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (5Z)-2-(2,6-dimethylphenyl)imino-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidin-4-one —— C23H24N2O3S
    (5Z)-2-(2,6-dimethylphenyl)imino-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidin-4-one
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]acetamide —— C20H24N2O4
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]acetamide
    —— 5-acetyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-2-carboxamide —— C19H21NO4S
    5-acetyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-2-carboxamide
    —— (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide —— C17H23NO5S
    (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide
    —— (2R)-N'-[5-(4-fluorophenyl)thiophene-2-carbonyl]-2,3-dihydro-1-benzofuran-2-carbohydrazide —— C20H15FN2O3S
    (2R)-N'-[5-(4-fluorophenyl)thiophene-2-carbonyl]-2,3-dihydro-1-benzofuran-2-carbohydrazide
    —— (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-phenylsulfanylprop-2-enamide —— C21H23NO3S
    (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-phenylsulfanylprop-2-enamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]heptan-1-amine —— C16H25NO
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]heptan-1-amine
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]heptan-1-amine —— C16H25NO
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]heptan-1-amine
    —— N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-methylphenoxy)acetamide —— C21H24N2O4
    N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-methylphenoxy)acetamide
    —— 1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-methoxyethyl)thiourea —— C16H23N3O3S
    1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-methoxyethyl)thiourea
    —— 1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-morpholin-4-ium-4-ylethyl)thiourea —— C19H29N4O3S+
    1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-morpholin-4-ium-4-ylethyl)thiourea
    —— 1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-methoxyethyl)thiourea —— C16H23N3O3S
    1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-methoxyethyl)thiourea
    —— 1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-morpholin-4-ylethyl)thiourea —— C19H28N4O3S
    1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-morpholin-4-ylethyl)thiourea
    —— 1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-morpholin-4-ylethyl)thiourea —— C19H28N4O3S
    1-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(2-morpholin-4-ylethyl)thiourea
    —— 2-(4-cyano-2-methoxyphenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C22H24N2O5
    2-(4-cyano-2-methoxyphenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 4-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1H-1,2,4-triazole-5-thione —— C14H16N4O2S
    4-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-1H-1,2,4-triazole-5-thione
    —— (1-Benzylpyrazol-4-yl)-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methanone —— C24H26N4O2
    (1-Benzylpyrazol-4-yl)-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methanone
    —— 1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-[(3S)-1,1-dioxothiolan-3-yl]sulfanylethanone —— C19H27N2O4S2+
    1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-[(3S)-1,1-dioxothiolan-3-yl]sulfanylethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-4-morpholin-4-ylbutane-1,4-dione —— C21H29N3O4
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-4-morpholin-4-ylbutane-1,4-dione
    —— 2-(2-Chlorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]ethanone —— C21H24ClN2O3+
    2-(2-Chlorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(2-methylphenyl)sulfanylethanone —— C22H27N2O2S+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(2-methylphenyl)sulfanylethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(5-phenylfuran-2-yl)propan-1-one —— C26H29N2O3+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-3-(5-phenylfuran-2-yl)propan-1-one
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(3-methylphenoxy)ethanone —— C22H26N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(3-methylphenoxy)ethanone
    —— 2-(2,5-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone —— C21H22F2N2O2S
    2-(2,5-Difluorophenyl)sulfanyl-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(3-ethyl-5-methyl-1,2-oxazol-4-yl)methanone —— C20H26N3O3+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(3-ethyl-5-methyl-1,2-oxazol-4-yl)methanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-ethylphenoxy)ethanone —— C23H28N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-ethylphenoxy)ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(2,3-dimethylphenoxy)ethanone —— C23H28N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(2,3-dimethylphenoxy)ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(3,5-dimethylphenoxy)ethanone —— C23H29N2O3+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(3,5-dimethylphenoxy)ethanone
    —— 1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(3S)-1,1-dioxothiolan-3-yl]sulfanylethanone —— C19H26N2O4S2
    1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(3S)-1,1-dioxothiolan-3-yl]sulfanylethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(2-methoxyphenoxy)ethanone —— C22H27N2O4+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(2-methoxyphenoxy)ethanone
    —— (2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-phenylsulfanylpropan-1-one —— C22H27N2O2S+
    (2R)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-phenylsulfanylpropan-1-one
    —— 4-[(2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-oxopropan-2-yl]oxybenzonitrile —— C23H25N3O3
    4-[(2S)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-1-oxopropan-2-yl]oxybenzonitrile
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-thiophen-2-ylethanone —— C19H23N2O2S+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-thiophen-2-ylethanone
    —— 4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-oxoethoxy]benzonitrile —— C22H23N3O3
    4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-oxoethoxy]benzonitrile
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N'-(2,3,4,5,6-pentafluorophenyl)acetohydrazide —— C18H15F5N2O3
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N'-(2,3,4,5,6-pentafluorophenyl)acetohydrazide
    —— (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(furan-2-yl)prop-2-enamide —— C19H21NO4
    (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(furan-2-yl)prop-2-enamide
    —— ethyl (1R,2S)-2-[[2,3-dihydro-1-benzofuran-5-ylmethyl-(1,5-dimethylpyrazole-3-carbonyl)amino]methyl]cyclopropane-1-carboxylate —— C22H27N3O4
    ethyl (1R,2S)-2-[[2,3-dihydro-1-benzofuran-5-ylmethyl-(1,5-dimethylpyrazole-3-carbonyl)amino]methyl]cyclopropane-1-carboxylate
    —— N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-[(1,5-dimethylpyrazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C22H27N3O2
    N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-[(1,5-dimethylpyrazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— (2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxooxolane-2-carboxamide —— C19H20ClN3O4
    (2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxooxolane-2-carboxamide
    —— (2S)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide —— C21H27NO3
    (2S)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide
    —— N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)cycloheptanecarboxamide —— C22H28ClN3O2
    N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)cycloheptanecarboxamide
    —— N-[(2-methylphenyl)methyl]-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C25H25NO2
    N-[(2-methylphenyl)methyl]-N-[(1S)-1-phenylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide