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-[cyclopentanecarbonyl-[(4-methylphenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H36N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(hept-6-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C35H46N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H37N3O8 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(cyclopropanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H40N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(pentanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H44N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(butanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(propanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H30N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(pent-4-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)-3-[benzyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H29ClN2O8 |
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—— | (3R,4S,4aS,9bS)-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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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(4-methylphenyl)methyl-(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H36N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-(oxolane-3-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-[cyclobutanecarbonyl-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31FN2O7 |
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—— | (3R,4S,4aS,9bS)-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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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[furan-3-ylmethyl(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H32N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H30N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[furan-3-ylmethyl-(2-methoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H28N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopentanecarbonyl-[(4-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H33FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(4-fluorophenyl)methyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H29FN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-hept-6-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H35FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H33FN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(cyclopentanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H34N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31ClN2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[furan-3-ylmethyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H30N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H29FN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H35FN2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(2-methoxyacetyl)-[(4-methylphenyl)methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[acetyl(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H33N3O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-octanoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H39FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H35N3O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H29FN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H37N3O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methoxypropanoyl(2-morpholin-4-ylethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H37N3O9 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[hept-6-enoyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H41N3O8 |
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—— | (3R,4S,4aS,9bS)-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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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H39N3O9 |
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—— | (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)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)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(4-methylphenyl)methyl-pent-4-enoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H34N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-(furan-3-ylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H28Cl2N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl-(2-cyclopentylacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H36N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl-[(4-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31FN2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(4-methylphenyl)methyl-octanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H42N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H42N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(4-fluorophenyl)methyl-(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[(4-methylphenyl)methyl]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-[(2-ethoxyacetyl)-(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H37N3O9 |
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