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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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(2-methoxyacetyl)-(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O9 |
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—— | 3-[3-ethoxypropyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O9 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[2-methoxyethyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H32N2O7 |
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—— | 3-[(2,4-dichlorophenyl)methyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32Cl2N2O5 |
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—— | 1-Dibenzofurancarboxylic acid, 1,9b-dihydro-4,9b-dimethyl-, methyl ester, cis- | —— | C16H16O3 |
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—— | 3-[acetyl-[(4-chlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H25ClN2O5 |
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—— | 3-[acetyl(cyclohexylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O7 |
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—— | 3-[cyclohexylmethyl(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H38N2O7 |
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—— | 3-[acetyl(cyclopentyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C22H28N2O5 |
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—— | 2-[4-Amino-6-(phenylamino)-1,3,5-triazin-2-yl]-2,3-dihydro-1-benzofuran-3-ol | —— | C17H15N5O2 |
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—— | 7-Nitro-2,3-dihydro-1-benzofuran-3,5-diol | —— | C8H7NO5 |
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—— | 3-[(2,4-dichlorophenyl)methyl-(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32Cl2N2O8 |
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—— | 3-[cyclopropanecarbonyl-[(2,4-dichlorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H28Cl2N2O7 |
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—— | (1R,9bS)-4,9b-Dimethyl-1,9b-dihydro-dibenzofuran-1-carboxylic acid methyl ester | —— | C16H16O3 |
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—— | 3-[acetyl-[(4-chlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H29ClN2O7 |
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—— | 3-[(4-chlorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H27ClN2O5 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(2-methylpropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[3-methoxypropanoyl-[(4-methylphenyl)methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H32N2O6 |
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—— | 3-[(2,4-dichlorophenyl)methyl-dodecanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H48Cl2N2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[2-methoxyethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C23H30N2O6 |
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—— | 3-[(2,6-Difluorophenyl)methyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazolidin-4-one | —— | C18H15F2NO2S |
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—— | 3-[dodecanoyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C35H48N2O5 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methylbutyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H36N2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[pent-4-enoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O8 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(oxolane-3-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H38N2O9 |
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—— | 3-[2-(3-fluorophenyl)ethyl-(3-methylbutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H35FN2O7 |
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—— | 3-[(2-fluorophenyl)methyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H29FN2O6 |
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—— | [1-[3-(Diethylazaniumyl)propyl]-2-(furan-2-yl)-4,5-dioxopyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate | —— | C25H30N2O5 |
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—— | 1-[3-(Diethylamino)propyl]-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione | —— | C25H30N2O5 |
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—— | Methyl 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 |
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—— | 3-[cyclohexyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
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—— | 3-[(2-fluorophenyl)methyl-(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H29FN2O5 |
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—— | 3-[(4-chlorophenyl)methyl-(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31ClN2O8 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[pentanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H29F3N2O7 |
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—— | 3-[(4-chlorophenyl)methyl-(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H33ClN2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[2-methoxyethyl(3-methoxypropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C22H30N2O7 |
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—— | 8-formyl-3-[furan-3-ylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H30N2O8 |
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—— | 3-[cyclobutanecarbonyl-[(2,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32Cl2N2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methylbutanoyl(3-methylbutyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H40N2O7 |
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—— | 3-[benzyl(3-methylbutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34N2O7 |
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—— | 3-[(2-cyclopentylacetyl)-[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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—— | 3-[3-ethoxypropyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O8 |
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—— | 3-[furan-3-ylmethyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H32N2O9 |
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—— | 3-[cyclohexyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O6 |
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—— | 3-[benzyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34N2O5 |
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—— | 3-[3-cyclopentylpropanoyl-[(4-methylphenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H40N2O7 |
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—— | 3-[acetyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H30N2O6 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(pent-4-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O8 |
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—— | 3-[(2,4-dichlorophenyl)methyl-(3-methylbutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32Cl2N2O7 |
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