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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)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(4-ethoxyphenyl)methyl]piperazin-1-yl]methanone —— C22H26N2O3
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(4-ethoxyphenyl)methyl]piperazin-1-yl]methanone
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(4-ethoxyphenyl)methyl]piperazin-1-yl]methanone —— C22H26N2O3
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(4-ethoxyphenyl)methyl]piperazin-1-yl]methanone
    —— N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethylphenyl)propanamide —— C22H27NO3
    N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethylphenyl)propanamide
    —— N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethylphenyl)propanamide —— C22H27NO3
    N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethylphenyl)propanamide
    —— (2R)-N-[3-[benzyl(methyl)amino]propyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H23ClN2O2
    (2R)-N-[3-[benzyl(methyl)amino]propyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-methylphenoxy)propanamide —— C21H25NO4
    (2R)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-methylphenoxy)propanamide
    —— (2S)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-methylphenoxy)propanamide —— C21H25NO4
    (2S)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-methylphenoxy)propanamide
    —— (2S)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-methylphenoxy)propanamide —— C21H25NO4
    (2S)-N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(3-methylphenoxy)propanamide
    —— (2S)-N-[3-[benzyl(methyl)amino]propyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H23ClN2O2
    (2S)-N-[3-[benzyl(methyl)amino]propyl]-5-chloro-2,3-dihydro-1-benzofuran-2-carboxamide
    —— methyl (1S,2S,3S,7Z,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 (1S,2S,3S,7Z,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 (1S,2S,3S,7Z,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 (1S,2S,3S,7Z,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 (1S,2S,3S,7Z,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 (1S,2S,3S,7Z,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
    —— [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone —— C19H22N2O4S2
    [(2S,3R)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone
    —— [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone —— C19H22N2O4S2
    [(2R,3S)-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone
    —— methyl (1S,2R,3S,7Z,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 (1S,2R,3S,7Z,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 (1S,2R,3S,7Z,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 (1S,2R,3S,7Z,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 (1S,2S,3S,7Z,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 (1S,2S,3S,7Z,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 (1S,2R,3S,7Z,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 (1S,2R,3S,7Z,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 (1S,2R,3S,7Z,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 (1S,2R,3S,7Z,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
    —— N-[(1R)-1-(3,4-diethoxyphenyl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C24H31NO5
    N-[(1R)-1-(3,4-diethoxyphenyl)ethyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— (2S)-5-chloro-N-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H15ClFNO2
    (2S)-5-chloro-N-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-[(3S)-1,1-dioxothiolan-3-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H25NO5S
    2-[(3S)-1,1-dioxothiolan-3-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-[(3R)-1,1-dioxothiolan-3-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H25NO5S
    2-[(3R)-1,1-dioxothiolan-3-yl]-N-[[(2S)-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-(thiophen-2-ylmethylsulfanyl)acetamide —— C19H23NO3S2
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(thiophen-2-ylmethylsulfanyl)acetamide
    —— 2-[(1R)-cyclopent-2-en-1-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C19H25NO3
    2-[(1R)-cyclopent-2-en-1-yl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-[(3R)-1,1-dioxothiolan-3-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H25NO5S
    2-[(3R)-1,1-dioxothiolan-3-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-[(3S)-1,1-dioxothiolan-3-yl]sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C18H25NO5S2
    2-[(3S)-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]-3-ethyl-5-methyl-1,2-oxazole-4-carboxamide —— C19H24N2O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-ethyl-5-methyl-1,2-oxazole-4-carboxamide
    —— 2-(2,5-difluorophenyl)sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H21F2NO3S
    2-(2,5-difluorophenyl)sulfanyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 2-[(1S)-cyclopent-2-en-1-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C19H25NO3
    2-[(1S)-cyclopent-2-en-1-yl]-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]-4-(4-methoxyphenoxy)butanamide —— C23H29NO5
    N-[[(2S)-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-(3-methylthiophen-2-yl)prop-2-enamide —— C20H23NO3S
    (E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-methylthiophen-2-yl)prop-2-enamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(thiophen-2-ylmethylsulfanyl)acetamide —— C19H23NO3S2
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(thiophen-2-ylmethylsulfanyl)acetamide
    —— 4-(2,5-dimethylthiophen-3-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-oxobutanamide —— C22H27NO4S
    4-(2,5-dimethylthiophen-3-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-oxobutanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)acetamide —— C20H22FNO4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenoxy)acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-propoxyphenoxy)acetamide —— C23H29NO5
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-propoxyphenoxy)acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide —— C23H24N2O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[3-(trifluoromethyl)pyrazol-1-yl]acetamide —— C18H20F3N3O3
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[3-(trifluoromethyl)pyrazol-1-yl]acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-morpholin-4-yl-4-oxobutanamide —— C20H28N2O5
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-morpholin-4-yl-4-oxobutanamide
    —— 3-cyclopentyl-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C20H29NO3
    3-cyclopentyl-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]-2-(3-ethylphenoxy)acetamide —— C22H27NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-ethylphenoxy)acetamide
    —— (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylpropanamide —— C21H25NO3S
    (2R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylpropanamide
    —— 4-(2,5-dimethylthiophen-3-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-oxobutanamide —— C22H27NO4S
    4-(2,5-dimethylthiophen-3-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-oxobutanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethylphenoxy)acetamide —— C22H27NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethylphenoxy)acetamide
    —— (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylpropanamide —— C21H25NO3S
    (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylpropanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenyl)sulfanylacetamide —— C20H22FNO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenyl)sulfanylacetamide
    —— 1-butyl-5-chloro-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-methylpyrazole-4-carboxamide —— C21H28ClN3O3
    1-butyl-5-chloro-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-methylpyrazole-4-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide —— C18H22N2O4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide
    —— (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylpropanamide —— C21H25NO3S
    (2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylpropanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethylphenoxy)acetamide —— C22H27NO4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethylphenoxy)acetamide