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。
中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
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—— | 3-[3-cyclopentylpropanoyl(3-methylbutyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O7 |
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—— | 3-[cyclohexyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O7 |
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—— | 3-[cyclohexyl(dodecanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C35H52N2O7 |
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—— | 3-[2-(3-fluorophenyl)ethyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O6 |
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—— | 3-[butanoyl(furan-3-ylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H30N2O8 |
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—— | 3-[cyclopropylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H32N2O5 |
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—— | 2-[6-methyl-4-(methylaminomethyl)-7-[(E)-1-methyliminopent-2-en-2-yl]oxy-5-[1-(4-methylphenyl)azepan-4-yl]-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol | —— | C33H47N3O3 |
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—— | 3-[hexyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H42N2O8 |
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—— | 3-[3-cyclopentylpropanoyl-[2-(3-methoxyphenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C34H42N2O8 |
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—— | 3-[hept-6-enoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H42N2O8 |
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—— | 5-[(3S)-3-[[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]amino]cyclopentyl]-1H-pyridin-2-one | —— | C20H24N2O2 |
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—— | 3-[dodecanoyl(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C35H53N3O8 |
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—— | 3-[cycloheptyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O5 |
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—— | (+/-) 2,2-Dimethyl-2,3-dihydro-benzofuran-7-carboxylic acid (4-oxo-2-pyridin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl)-amide | 1036716-48-9 | C23H22N4O3 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H35N3O8 |
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—— | 3-[1-adamantylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C35H48N2O7 |
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—— | 3-(6-chloropyridin-3-yl)-N'-[[1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]piperidin-4-yl]methyl]-2-imidazol-1-ylbutanediamide | —— | C29H35ClN6O3 |
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—— | 3-[dodecanoyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C37H51FN2O7 |
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—— | 3-[cyclopropylmethyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H32N2O7 |
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—— | 3-[butanoyl-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O7 |
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—— | 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(3-methylbutyl)acetamide | 762255-18-5 | C17H25NO3 |
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—— | 2,3-dihydro-benzofuran-4-carboxylic acid [(R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-thiazolidin-4-ylmethyl]-amide | 1061589-58-9 | C25H25N3O3S2 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O8 |
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—— | methyl 2-[(2S,3R)-5-hydroxy-2-methoxy-6-methyl-2,3-dihydro-1-benzofuran-3-yl]benzoate | —— | C18H18O5 |
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—— | 3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H29ClN2O5 |
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—— | [1-[3-(Diethylazaniumyl)propyl]-4,5-dioxo-2-thiophen-2-ylpyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate | —— | C25H30N2O4S |
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—— | 1-[3-(Diethylamino)propyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione | —— | C25H30N2O4S |
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—— | 3-[cyclobutanecarbonyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H28N2O6 |
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—— | 3-[cycloheptyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O7 |
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—— | 3-[cycloheptyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O8 |
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—— | 3-[cyclobutanecarbonyl(cycloheptyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O7 |
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—— | 3-[cycloheptyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O7 |
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—— | 3-[benzyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34N2O8 |
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—— | 1-(2,3-dihydro-1-benzofuran-5-yl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone | —— | C12H11N3O2 |
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—— | 4-methyl-6-methylidene-N-[1-(3-methyl-2-methylidene-3H-1-benzofuran-6-yl)hexan-2-yl]-5-propylcyclohexa-2,4-dien-1-imine | —— | C27H35NO |
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—— | (9aS)-8-acetyl-N-benzyl-1-hydroxy-9a-methyl-7,9-dioxo-3-phenylmethoxydibenzofuran-4-carboxamide | —— | C30H25NO7 |
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—— | 3-[cyclopropylmethyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H50N2O7 |
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—— | 3-[(3,4-dichlorophenyl)methyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32Cl2N2O5 |
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—— | 3-[3-ethoxypropyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O9 |
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—— | 3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O5 |
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—— | (8-hydroxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-yl) hydrogen carbonate | —— | C18H16O5 |
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—— | 1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-3-[(2-methoxyphenyl)methylamino]propan-2-ol | —— | C21H27NO4 |
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—— | 3-[1-adamantylmethyl(cyclobutanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H44N2O7 |
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—— | 3-[cyclobutanecarbonyl(cyclohexylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O5 |
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—— | 4-(Cyclopropylmethyl)-10,14-dimethoxy-15-(phenylmethoxymethyl)-12-oxa-4-azapentacyclo[9.7.1.01,13.05,17.07,19]nonadeca-7(19),8,10-triene | —— | C31H39NO4 |
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—— | methyl N-[[7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate | —— | C18H19NO3 |
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—— | C-[7-(2,5-difluoro-phenyl)-2,3-dihydro-benzofuran-2-yl]-methylamine | —— | C15H13F2NO |
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—— | 4b,9b-Bis(2,3,4,5,6-pentamethylphenyl)-[1]benzofuro[3,2-b][1]benzofuran | —— | C36H38O2 |
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—— | tert-butyl N-tert-butyl-N-[3-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)propoxycarbonyl]carbamate | —— | C23H35NO5 |
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—— | N-[2-(3-methyl-2,5,6,7-tetrahydrofuro[3,2-g]chromen-3-yl)phenyl]-N-(oxolan-2-ylmethyl)formamide | —— | C24H27NO4 |
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