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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
    —— N-[2-(2-Oxo-1,3-oxazinan-3-YL)ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C15H18N2O4
    N-[2-(2-Oxo-1,3-oxazinan-3-YL)ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)-1-isobutyl-2-piperazinyl]ethanol —— C19H30N2O2
    2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)-1-isobutyl-2-piperazinyl]ethanol
    —— N-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-3-pyridin-3-ylpropanamide —— C19H22N2O2
    N-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-3-pyridin-3-ylpropanamide
    —— N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-N,1-dimethyl-5-(2-thienyl)-1H-pyrazole-3-carboxamide —— C19H19N3O2S
    N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-N,1-dimethyl-5-(2-thienyl)-1H-pyrazole-3-carboxamide
    —— N-[(6-Hydroxy-2-methylpyrimidin-4-YL)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C15H15N3O3
    N-[(6-Hydroxy-2-methylpyrimidin-4-YL)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-{trans-3-[5-(1H-imidazol-1-ylmethyl)-4-methyl-4H-1,2,4-triazol-3-yl]cyclobutyl}-2,3-dihydro-1-benzofuran-5-carboxamide —— C20H22N6O2
    N-{trans-3-[5-(1H-imidazol-1-ylmethyl)-4-methyl-4H-1,2,4-triazol-3-yl]cyclobutyl}-2,3-dihydro-1-benzofuran-5-carboxamide
    —— methyl (7E)-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 (7E)-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
    —— N-[(3-methylimidazo[2,1-b][1,3]thiazol-6-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H15N3O2S
    N-[(3-methylimidazo[2,1-b][1,3]thiazol-6-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[1-(6-Methylpyridin-3-YL)ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C17H18N2O2
    N-[1-(6-Methylpyridin-3-YL)ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[trans-3-(6-oxo-1,6-dihydropyrimidin-4-yl)cyclobutyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C17H17N3O3
    N-[trans-3-(6-oxo-1,6-dihydropyrimidin-4-yl)cyclobutyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 6-(trans-3-aminocyclobutyl)-N~4~-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]pyrimidine-2,4-diamine —— C19H25N5O
    6-(trans-3-aminocyclobutyl)-N~4~-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]pyrimidine-2,4-diamine
    —— N-[cis-4-(cyclopropylmethoxy)tetrahydro-2H-pyran-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C18H23NO4
    N-[cis-4-(cyclopropylmethoxy)tetrahydro-2H-pyran-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-(2,3-dihydro-1-benzofuran-3-yl)-2-(2-ethyl-4-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)acetamide —— C17H19N3O3
    N-(2,3-dihydro-1-benzofuran-3-yl)-2-(2-ethyl-4-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)acetamide
    —— 2-methyl-N-(5-morpholin-4-ylpentyl)-2,3-dihydro-1-benzofuran-5-carboxamide —— C19H28N2O3
    2-methyl-N-(5-morpholin-4-ylpentyl)-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 1-(difluoromethyl)-N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-N-methyl-1H-pyrazole-3-carboxamide —— C15H15F2N3O2
    1-(difluoromethyl)-N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-N-methyl-1H-pyrazole-3-carboxamide
    —— N-[trans-3-(5-{[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]methyl}-4-methyl-4H-1,2,4-triazol-3-yl)cyclobutyl]acetamide —— C20H26N4O3
    N-[trans-3-(5-{[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]methyl}-4-methyl-4H-1,2,4-triazol-3-yl)cyclobutyl]acetamide
    —— 1-[3-(diethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(pyridin-4-yl)-1,5-dihydro-2H-pyrrol-2-one —— C26H31N3O4
    1-[3-(diethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(pyridin-4-yl)-1,5-dihydro-2H-pyrrol-2-one
    —— N-{rac-7-[(methylsulfonyl)amino]-2-oxabicyclo[3.2.0]hept-6-yl}-2,3-dihydro-1-benzofuran-5-carboxamide —— C16H20N2O5S
    N-{rac-7-[(methylsulfonyl)amino]-2-oxabicyclo[3.2.0]hept-6-yl}-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[2,3-dihydro-1-benzofuran-5-yl(cis-3-hydroxycyclobutyl)methyl]-3-pyridin-3-ylpropanamide —— C21H24N2O3
    N-[2,3-dihydro-1-benzofuran-5-yl(cis-3-hydroxycyclobutyl)methyl]-3-pyridin-3-ylpropanamide
    —— 3-[2-(3-{[(2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]amino}-3-oxopropyl)-5-oxopyrrolidin-2-yl]propanoic acid —— C21H28N2O5
    3-[2-(3-{[(2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]amino}-3-oxopropyl)-5-oxopyrrolidin-2-yl]propanoic acid
    —— N-{cis-3-[5-(hydroxymethyl)-4-(2-methoxyethyl)-4H-1,2,4-triazol-3-yl]cyclobutyl}-2,3-dihydro-1-benzofuran-5-carboxamide —— C19H24N4O4
    N-{cis-3-[5-(hydroxymethyl)-4-(2-methoxyethyl)-4H-1,2,4-triazol-3-yl]cyclobutyl}-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide —— C19H22N2O3
    N-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-4,5,6,7-tetrahydro-1,2-benzisoxazole-3-carboxamide
    —— 1,5-anhydro-2-O-(cyclobutylmethyl)-3,4-dideoxy-3-[(2,3-dihydro-1-benzofuran-5-ylcarbonyl)amino]-D-threo-pentitol —— C19H25NO4
    1,5-anhydro-2-O-(cyclobutylmethyl)-3,4-dideoxy-3-[(2,3-dihydro-1-benzofuran-5-ylcarbonyl)amino]-D-threo-pentitol
    —— N-[2,3-dihydro-1-benzofuran-5-yl(cis-3-hydroxycyclobutyl)methyl]-3-pyridin-4-ylpropanamide —— C21H24N2O3
    N-[2,3-dihydro-1-benzofuran-5-yl(cis-3-hydroxycyclobutyl)methyl]-3-pyridin-4-ylpropanamide
    —— N-[2,3-dihydro-1-benzofuran-5-yl(cis-3-hydroxycyclobutyl)methyl]cyclopentanecarboxamide —— C19H25NO3
    N-[2,3-dihydro-1-benzofuran-5-yl(cis-3-hydroxycyclobutyl)methyl]cyclopentanecarboxamide
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(oxolan-2-ylmethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C23H23NO5S
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(oxolan-2-ylmethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— 1-(2,3-Dihydrobenzofuran-5-yl)ethanethione —— C10H10OS
    1-(2,3-Dihydrobenzofuran-5-yl)ethanethione
    —— 3-(5-Bromo-2,3-dihydro-1-benzofuran-7-YL)propan-1-OL —— C11H13BrO2
    3-(5-Bromo-2,3-dihydro-1-benzofuran-7-YL)propan-1-OL
    —— 3-(5-Bromo-2,3-dihydro-1-benzofuran-7-yl)propanal —— C11H11BrO2
    3-(5-Bromo-2,3-dihydro-1-benzofuran-7-yl)propanal
    —— 1-(8-Bromo-2,3,6,7-tetrahydrodibenzo[1,2-b; 4,5-b']difuran-4-yl-2-aminoethane, TFA —— C14H13BrF3NO3
    1-(8-Bromo-2,3,6,7-tetrahydrodibenzo[1,2-b; 4,5-b']difuran-4-yl-2-aminoethane, TFA
    —— 1-[(2Z)-5,7-dichloro-2-[2-(2,4-dichlorophenoxy)ethylidene]-3H-1-benzofuran-3-yl]piperidine —— C21H19Cl4NO2
    1-[(2Z)-5,7-dichloro-2-[2-(2,4-dichlorophenoxy)ethylidene]-3H-1-benzofuran-3-yl]piperidine
    —— 5-Benzofuranol, 2,3-dihydro-3,3-dimethyl-2-(methylphenylamino)-6-(1,1,3,3-tetramethylbutyl)- —— C25H35NO2
    5-Benzofuranol, 2,3-dihydro-3,3-dimethyl-2-(methylphenylamino)-6-(1,1,3,3-tetramethylbutyl)-
    —— 2-Dibenzofuranol, 5a,6,7,8,9,9a-hexahydro-5a-methyl-8-(1-methylethyl)-3-octyl- —— C24H38O2
    2-Dibenzofuranol, 5a,6,7,8,9,9a-hexahydro-5a-methyl-8-(1-methylethyl)-3-octyl-
    —— 2-Dibenzofuranol, 7,8,9,9a-tetrahydro-3-(1,1,3,3-tetramethylbutyl)- —— C20H28O2
    2-Dibenzofuranol, 7,8,9,9a-tetrahydro-3-(1,1,3,3-tetramethylbutyl)-
    —— Methyl-(E)-2-methoxy-2,3-dihydrobenzofuran-3-carboxylat —— C11H12O4
    Methyl-(E)-2-methoxy-2,3-dihydrobenzofuran-3-carboxylat
    —— 3-[hydroxy(2-thienyl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5,6-dicarbonitrile —— C16H12N2O2S
    3-[hydroxy(2-thienyl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5,6-dicarbonitrile
    —— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(oxolan-2-ylmethyl)-5-pyridin-4-ylpyrrolidine-2,3-dione —— C24H24N2O5
    (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(oxolan-2-ylmethyl)-5-pyridin-4-ylpyrrolidine-2,3-dione
    —— 5-fluoro-2-{(2Z)-2-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]hydrazinyl}-4-(pyrrolidin-1-yl)pyrimidine —— C18H20FN5O
    5-fluoro-2-{(2Z)-2-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]hydrazinyl}-4-(pyrrolidin-1-yl)pyrimidine
    —— (E)-3-(furan-2-yl)-1-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)prop-2-en-1-one —— C16H14O3
    (E)-3-(furan-2-yl)-1-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)prop-2-en-1-one
    —— 4a,8-dimethyl-2,3,4,9b-tetrahydro-1H-dibenzofuran-2-ol —— C14H18O2
    4a,8-dimethyl-2,3,4,9b-tetrahydro-1H-dibenzofuran-2-ol
    —— 5a,8-dimethyl-7,8,9,9a-tetrahydro-6H-dibenzofuran-2-ol —— C14H18O2
    5a,8-dimethyl-7,8,9,9a-tetrahydro-6H-dibenzofuran-2-ol
    —— 3-(4,6-Difluoro-2,3-dihydro-1-benzofuran-3-yl)-1-methyl-1-prop-2-enylurea —— C13H14F2N2O2
    3-(4,6-Difluoro-2,3-dihydro-1-benzofuran-3-yl)-1-methyl-1-prop-2-enylurea
    —— 1-(5-Chloro-2,3-dihydro-1-benzofuran-7-yl)-3-(3-hydroxypentyl)urea —— C14H19ClN2O3
    1-(5-Chloro-2,3-dihydro-1-benzofuran-7-yl)-3-(3-hydroxypentyl)urea
    —— N,3-dimethyl-N-[2-(2H-tetrazol-5-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H19N5O2
    N,3-dimethyl-N-[2-(2H-tetrazol-5-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 4-[3-(2,3-Dihydro-1-benzofuran-5-yl)propyl]-2,5,5-trimethylmorpholine —— C18H27NO2
    4-[3-(2,3-Dihydro-1-benzofuran-5-yl)propyl]-2,5,5-trimethylmorpholine
    —— N-(2,3-dihydro-1-benzofuran-3-yl)-2-prop-2-ynylpent-4-ynamide —— C16H15NO2
    N-(2,3-dihydro-1-benzofuran-3-yl)-2-prop-2-ynylpent-4-ynamide
    —— (5E)-5-[3-(2,3-dihydro-1-benzofuran-5-yl)-2H-1,2,4-oxadiazol-5-ylidene]-2-methylpyridin-4-one —— C16H13N3O3
    (5E)-5-[3-(2,3-dihydro-1-benzofuran-5-yl)-2H-1,2,4-oxadiazol-5-ylidene]-2-methylpyridin-4-one
    —— 4-[3-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-5-yl]-1-(1H-pyrazol-4-yl)pyrrolidin-2-one —— C17H15N5O3
    4-[3-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-5-yl]-1-(1H-pyrazol-4-yl)pyrrolidin-2-one
    —— (5,6-Dimethyl-2,3-dihydro-1-benzofuran-2-yl)-[2-(hydroxymethyl)pyrrolidin-1-yl]methanone —— C16H21NO3
    (5,6-Dimethyl-2,3-dihydro-1-benzofuran-2-yl)-[2-(hydroxymethyl)pyrrolidin-1-yl]methanone
    —— N-(5-chloro-2,3-dihydro-1-benzofuran-7-yl)-2-(1H-pyrazol-5-yl)acetamide —— C13H12ClN3O2
    N-(5-chloro-2,3-dihydro-1-benzofuran-7-yl)-2-(1H-pyrazol-5-yl)acetamide