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-[cyclohexyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopentanecarbonyl-[[(2S)-oxolan-2-yl]methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[acetyl-[(2,4-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-[(3,4-dichlorophenyl)methyl-pent-4-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H32Cl2N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(2-methoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H31ClN2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[(2-methoxyacetyl)-(2-morpholin-4-ylethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H37N3O9 |
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—— | 1-(2,3-dihydro-1-benzofuran-5-yl)-N-[[4-methyl-2-[(3S)-oxolan-3-yl]oxyphenyl]methyl]methanamine | —— | C21H25NO3 |
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—— | (3R,4S,4aS,9bS)-3-[1-adamantylmethyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C40H60N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(4-fluorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H31FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopentanecarbonyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H42N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[[(2S)-oxolan-2-yl]methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2,4-dichlorophenyl)methyl-(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34Cl2N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[hept-6-enoyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H42N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(2-fluorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H31FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H32Cl2N2O8 |
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—— | 1-(2,3-dihydro-1-benzofuran-5-yl)-N-[[4-methyl-2-[(3R)-oxolan-3-yl]oxyphenyl]methyl]methanamine | —— | C21H25NO3 |
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—— | (3R,4S,4aS,9bS)-3-[(4-fluorophenyl)methyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H37FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[butanoyl-[2-(2-methoxyphenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H36N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methoxypropanoyl(3-methylbutyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H38N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[hexyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H40N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(octanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H47N3O8 |
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—— | (3R,4S,4aS,9bS)-3-[(2-ethoxyacetyl)-[[(2S)-oxolan-2-yl]methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[(2,4-dichlorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32Cl2N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclohexyl(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopentanecarbonyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H41N3O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methylbutyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclohexyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclobutanecarbonyl(cyclopentyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O7 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H32N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl-[2-(3-fluorophenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H39FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[acetyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H36N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[dodecanoyl-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H47FN2O7 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O7 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methylbutanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H42N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[oxolane-3-carbonyl-[[(2R)-oxolan-2-yl]methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[(3,4-dichlorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H30Cl2N2O7 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[propanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H38N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H36N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[dodecanoyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C34H48N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[hept-6-enoyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H40N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(3-methoxyphenyl)ethyl-(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H34N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[(2-cyclopentylacetyl)-[(3,4-dichlorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H34Cl2N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(3,4-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)-3-[cyclopentanecarbonyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-(oxolane-3-carbonyl)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-[(2-cyclopentylacetyl)-(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H41N3O8 |
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—— | (3R,4S,4aS,9bS)-3-[cyclopropanecarbonyl-[2-(3-methoxyphenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H34N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-3-[furan-3-ylmethyl(oxolane-2-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)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(oxolane-3-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H36N2O9 |
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