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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
    —— 5-(carbamoylamino)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]pentanamide —— C18H27N3O4
    5-(carbamoylamino)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]pentanamide
    —— 2-[(1R)-cyclopent-2-en-1-yl]-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C19H25NO3
    2-[(1R)-cyclopent-2-en-1-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]-2-[2-(2-oxopyrrolidin-1-yl)-1,3-thiazol-4-yl]acetamide —— C21H25N3O4S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-(2-oxopyrrolidin-1-yl)-1,3-thiazol-4-yl]acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-methyl-5-propan-2-yl-1,2-oxazole-4-carboxamide —— C20H26N2O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-methyl-5-propan-2-yl-1,2-oxazole-4-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-ethyl-5-methyl-1,2-oxazole-4-carboxamide —— C19H24N2O4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-ethyl-5-methyl-1,2-oxazole-4-carboxamide
    —— (2R)-5-chloro-N-[(2-chlorophenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H13Cl2NO2
    (2R)-5-chloro-N-[(2-chlorophenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 4-(4-acetylpiperazin-1-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-oxobutanamide —— C22H31N3O5
    4-(4-acetylpiperazin-1-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-formyl-2-methoxyphenoxy)acetamide —— C22H25NO6
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-formyl-2-methoxyphenoxy)acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-(phenoxymethyl)furan-2-carboxamide —— C24H25NO5
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-(phenoxymethyl)furan-2-carboxamide
    —— (2R)-2-(4-cyanophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C22H24N2O4
    (2R)-2-(4-cyanophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide
    —— N-[[(2S)-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-[[(2S)-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-(3-chlorophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H22ClNO4
    2-(3-chlorophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— (2S)-2-(4-cyanophenoxy)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C22H24N2O4
    (2S)-2-(4-cyanophenoxy)-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]-3,5-dimethylpyrazole-4-carboxamide —— C25H29N3O3
    1-benzyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,5-dimethylpyrazole-4-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide —— C18H22N2O4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-thiophen-2-ylbutanamide —— C20H25NO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-thiophen-2-ylbutanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylacetamide —— C20H23NO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-phenylsulfanylacetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide —— C23H24N2O4
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-methyl-3-phenyl-1,2-oxazole-4-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-propoxyphenoxy)acetamide —— C23H29NO5
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-propoxyphenoxy)acetamide
    —— 3-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C20H26N2O4
    3-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[[(2S)-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]-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamide —— C20H23NO3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenyl)sulfanylacetamide —— C20H22FNO3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-fluorophenyl)sulfanylacetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethoxyphenoxy)acetamide —— C22H27NO5
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethoxyphenoxy)acetamide
    —— 2-(2,6-dimethylphenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C22H27NO4
    2-(2,6-dimethylphenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
    —— 3-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]propanamide —— C20H26N2O4
    3-(3,5-dimethyl-1,2-oxazol-4-yl)-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]-3-(2-methylphenoxy)propanamide —— C22H27NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(2-methylphenoxy)propanamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethoxyphenoxy)acetamide —— C22H27NO5
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-ethoxyphenoxy)acetamide
    —— (2E,4E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]hexa-2,4-dienamide —— C18H23NO3
    (2E,4E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]hexa-2,4-dienamide
    —— 5-chloro-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-2-carboxamide —— C17H18ClNO3S
    5-chloro-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-2-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-methoxyphenoxy)acetamide —— C21H25NO5
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(4-methoxyphenoxy)acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)pentanamide —— C20H26N2O4S2
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-5-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)pentanamide
    —— 2-(3-bromophenoxy)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H22BrNO4
    2-(3-bromophenoxy)-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]-3-methylbutanamide —— C17H25NO3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-methylbutanamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-fluorophenoxy)acetamide —— C20H22FNO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-fluorophenoxy)acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)acetamide —— C21H25NO4
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(3-methylphenoxy)acetamide
    —— (Z)-3-[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C17H16N2O2S
    (Z)-3-[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile
    —— (Z)-3-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C17H16N2O2S
    (Z)-3-[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(4-methyl-1,3-thiazol-2-yl)prop-2-enenitrile
    —— (2S)-N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-2-(4-fluorophenoxy)propanehydrazide —— C21H23FN2O5
    (2S)-N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-2-(4-fluorophenoxy)propanehydrazide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-1-[(Z)-3-phenylprop-2-enyl]triazole-4-carboxamide —— C22H22N4O2
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-1-[(Z)-3-phenylprop-2-enyl]triazole-4-carboxamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-1-[(Z)-3-phenylprop-2-enyl]triazole-4-carboxamide —— C22H22N4O2
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-1-[(Z)-3-phenylprop-2-enyl]triazole-4-carboxamide
    —— (5E)-5-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione —— C14H13NO4S
    (5E)-5-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione
    —— (5E)-5-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione —— C14H13NO4S
    (5E)-5-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione
    —— 4-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-methyl-1H-1,2,4-triazole-5-thione —— C15H18N4O2S
    4-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-methyl-1H-1,2,4-triazole-5-thione
    —— 2-(4-chlorophenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide —— C20H21ClN2O4
    2-(4-chlorophenoxy)-N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]acetamide
    —— 4-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-thione —— C15H15F3N4O2S
    4-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-thione
    —— N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(4-ethylphenoxy)acetamide —— C22H26N2O4
    N-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(4-ethylphenoxy)acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(6-oxo-4-propyl-1H-pyrimidin-2-yl)sulfanyl]acetamide —— C21H27N3O4S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(6-oxo-4-propyl-1H-pyrimidin-2-yl)sulfanyl]acetamide
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(S)-phenyl(thiophen-2-yl)methyl]acetamide —— C23H23NO3S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(S)-phenyl(thiophen-2-yl)methyl]acetamide
    —— 2-[[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-thiophen-2-yl-1H-1,2,4-triazole-3-thione —— C20H25N5OS2+2
    2-[[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine-1,4-diium-1-yl]methyl]-5-thiophen-2-yl-1H-1,2,4-triazole-3-thione
    —— 2-[[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-thiophen-2-yl-1H-1,2,4-triazole-3-thione —— C20H23N5OS2
    2-[[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]methyl]-5-thiophen-2-yl-1H-1,2,4-triazole-3-thione