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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—— | (3R,4S,4aS,9bS)-3-[(4-fluorophenyl)methyl-(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31FN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[dodecanoyl(2-methoxyethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H48N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-ethoxyacetyl)-[(4-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[hexyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopentyl(cyclopropanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H32N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[butanoyl(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H37N3O8 |
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—— | (3R,4S,4aS,9bS)-3-[cycloheptyl(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H40N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[cyclohexyl(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(3-methoxyphenyl)ethyl-(oxolane-2-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H36N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl(cycloheptyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H38N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-hept-6-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H37FN2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[propanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C22H25F3N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(hept-6-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H36N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methylpropanoyl(2-morpholin-4-ylethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H37N3O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(4-methylphenyl)methyl-(oxolane-2-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H34N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[butanoyl-[(4-chlorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31ClN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(2,4-dichlorophenyl)methyl-pent-4-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H30Cl2N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[octanoyl-[[(2R)-oxolan-2-yl]methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-hexylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[3-ethoxypropyl(3-methylbutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methoxyethyl(octanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H30N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(3-cyclopentylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H38N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[acetyl(cyclohexylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H32N2O5 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(pent-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(propanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H40N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methoxyethyl(pentanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[acetyl(cyclohexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H32N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(pent-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H42N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[pent-2-enoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[acetyl-[(4-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H27FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclohexylmethyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H38N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-(2,2,2-trifluoroethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H31F3N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopentanecarbonyl(3-methylbutyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(2-cyclopentylacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H35ClN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[acetyl-[(3,4-dichlorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H26Cl2N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(4-fluorophenyl)methyl-(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopropylmethyl(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H30N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(cyclopentanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C34H44N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[hexyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl-(2-ethoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H42N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(3-cyclopentylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H48N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopentanecarbonyl-[[(2S)-oxolan-2-yl]methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H36N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[oxolane-2-carbonyl-[[(2R)-oxolan-2-yl]methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H34N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[cyclohexyl(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H36N2O7 |
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—— | (3R,4S,4aS,9bS)-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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—— | (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-pent-2-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31ClN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[butanoyl(hexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[octanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H46N2O8 |
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