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-[(2-fluorophenyl)methyl-(2-methoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H31FN2O8 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[(2-methoxyacetyl)-(2-morpholin-4-ylethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H33N3O7 |
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—— | 3-[(2-cyclopentylacetyl)-(2,2,2-trifluoroethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H29F3N2O5 |
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—— | 3-[3-ethoxypropyl(propanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O8 |
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—— | 3-[cyclohexylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H42N2O7 |
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—— | 3-[(3,4-dichlorophenyl)methyl-pentanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H30Cl2N2O5 |
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—— | 3-[benzyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32N2O8 |
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—— | 3-[(2-ethoxyacetyl)-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O8 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[2-(3-methoxyphenyl)ethyl-(3-methylbutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H36N2O6 |
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—— | 3-[cyclohexyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C35H54N2O7 |
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—— | 3-[cyclopropylmethyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H46N2O5 |
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—— | 4-(2,3-Dihydro-1-benzofuran-2-ylmethyl)morpholin-4-ium | —— | C13H18NO2+ |
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—— | 3-[butanoyl(3-ethoxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H34N2O6 |
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—— | 3-[butanoyl(cyclopentyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O7 |
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—— | 3-[cyclopentanecarbonyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H36N2O6 |
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—— | 3-[cyclopentyl(octanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O7 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-pentanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H38N2O8 |
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—— | 3-[cyclohexylmethyl(dodecanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H54N2O7 |
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—— | 3-[3-ethoxypropyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H46N2O8 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[2-methoxyethyl(octanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H38N2O6 |
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—— | 3-[cyclopentyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O5 |
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—— | 3-[(2-cyclopentylacetyl)-(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O8 |
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—— | [1-[2-(dimethylazaniumyl)ethyl]-4,5-dioxo-2-thiophen-2-ylpyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate | —— | C22H24N2O4S |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[2-oxobutanoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H30N2O7 |
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—— | 3-[cyclohexyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H32N2O5 |
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—— | 3-[acetyl(cyclohexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C23H30N2O5 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[5-oxohexanoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O7 |
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—— | 3-[cyclohexyl(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O5 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[oxolane-3-carbonyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H32N2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H37N3O9 |
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—— | 3-[(2-ethoxyacetyl)-(furan-3-ylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H30N2O9 |
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—— | 3-[hexyl-(2-methoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H38N2O8 |
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—— | 3-[benzyl(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H34N2O7 |
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—— | 3-[cyclohexyl-(2-ethoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O8 |
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—— | (R)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl-[(2S)-2,3-dihydro-1-benzofuran-2-yl]methanamine | —— | C18H19NO3 |
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—— | 3-[benzyl(pent-4-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32N2O7 |
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—— | 3-[(4-chlorophenyl)methyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H33ClN2O7 |
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—— | (R)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl-[(2R)-2,3-dihydro-1-benzofuran-2-yl]methanamine | —— | C18H19NO3 |
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—— | 3-[1-adamantylmethyl(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H40N2O5 |
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—— | 3-[cyclopentanecarbonyl-[(2-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H35FN2O7 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methoxypropanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C23H27F3N2O8 |
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—— | 3-[(2-fluorophenyl)methyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H29FN2O5 |
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—— | 3-[cyclohexylmethyl(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
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—— | 3-[acetyl-[2-(3-methoxyphenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32N2O8 |
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—— | 3-[(4-chlorophenyl)methyl-(3-cyclopentylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H35ClN2O5 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[(2-methoxyacetyl)-(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C20H23F3N2O6 |
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—— | Methyl 5-(2,3-dihydro-1-benzofuran-5-yl)thiophene-2-carboxylate | —— | C14H12O3S |
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—— | (((2,2,7-Trimethyl-3-oxaindan-4-YL)amino)methylene)methane-1,1-dicarbonitrile | —— | C15H15N3O |
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—— | 3-[(3,4-dichlorophenyl)methyl-(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H30Cl2N2O8 |
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—— | 3-[dodecanoyl(2,2,2-trifluoroethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H45F3N2O7 |
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