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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—— | N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylsulfonylpiperidine-4-carboxamide | —— | C16H22N2O4S |
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—— | N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylsulfonylpiperidine-4-carboxamide | —— | C16H22N2O4S |
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—— | 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[[6-[(2S,6S)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]methyl]acetamide | —— | C22H27N3O3 |
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—— | (2S)-5-chloro-N'-pyrimidin-2-yl-2,3-dihydro-1-benzofuran-2-carbohydrazide | —— | C13H11ClN4O2 |
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—— | (2S)-5-chloro-N-[1-(5-methyl-1,2,4-oxadiazol-3-yl)cycloheptyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C19H22ClN3O3 |
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—— | 2,3-dihydro-1-benzofuran-5-yl-[(2R)-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)pyrrolidin-1-yl]methanone | —— | C20H24N4O2 |
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—— | (2S)-5-chloro-N-[1-[(2-chlorophenyl)methyl]-6-oxopyridin-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C21H16Cl2N2O3 |
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—— | (2S)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3-fluorophenoxy)propanamide | —— | C18H18FNO3 |
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—— | (2S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylpentanamide | —— | C15H21NO2 |
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—— | (2R)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3-fluorophenoxy)propanamide | —— | C18H18FNO3 |
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—— | (5S,7R)-3-bromo-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]adamantane-1-carboxamide | —— | C20H24BrNO2 |
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—— | N-[(2S)-2-(4-methoxyphenyl)-2-pyrrolidin-1-ylethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide | —— | C21H26N2O4S |
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—— | (2R)-N-[(2S)-2-morpholin-4-yl-2-[(3S)-oxolan-3-yl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C19H26N2O4 |
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—— | 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[[3-(1,2,4-triazol-1-ylmethyl)phenyl]methyl]urea | —— | C20H21N5O2 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H41N3O9 |
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—— | (3R,4S,4aS,9bS)-3-[dodecanoyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H52N2O5 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methylbutyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H40N2O8 |
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—— | (3R,4S,4aS,9bS)-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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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbut-2-enoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-3-[2-morpholin-4-ylethyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H37N3O7 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-3-[2-(3-methoxyphenyl)ethyl-(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H36N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methoxyethyl(3-methylbutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O9 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-oxobutanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C23H27F3N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[pent-2-enoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H29F3N2O7 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(octanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H42N2O8 |
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—— | (3R,4S,4aS,9bS)-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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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(3-methoxyphenyl)ethyl-(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H36N2O9 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methylbut-2-enoyl-[(4-methylphenyl)methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H36N2O7 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[5-oxohexanoyl-[[(2S)-oxolan-2-yl]methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[cycloheptyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-oxobutanoyl-[[(2S)-oxolan-2-yl]methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H32N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[3-cyclopentylpropanoyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-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-[2-(3-methoxyphenyl)ethyl-(3-methylbut-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H36N2O8 |
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—— | (3R,4S,4aS,9bS)-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methoxypropanoyl-[(4-methylphenyl)methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34N2O8 |
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—— | (3R,4S,4aS,9bS)-3-[hexyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H42N2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-3-[5-oxohexanoyl-[[(2R)-oxolan-2-yl]methyl]amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[benzyl(3-cyclopentylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H36N2O5 |
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—— | (3R,4S,4aS,9bS)-3-[(4-fluorophenyl)methyl-(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H35FN2O8 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-(3-methoxyphenyl)ethyl-(oxolane-3-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H38N2O9 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-oxobutanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O9 |
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—— | (3R,4S,4aS,9bS)-3-[cycloheptyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H42N2O7 |
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—— | (3R,4S,4aS,9bS)-4-hydroxy-N-(2-hydroxyethyl)-3-[2-oxobutanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O7 |
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—— | (3R,4S,4aS,9bS)-3-[(4-chlorophenyl)methyl-(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H35ClN2O8 |
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—— | (3R,4S,4aS,9bS)-3-[2-(3-fluorophenyl)ethyl-(2-oxobutanoyl)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-[butanoyl-[[(2R)-oxolan-2-yl]methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O8 |
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—— | 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-[(2-methyl-1,3-thiazol-4-yl)methyl]urea | —— | C15H17N3O2S |
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—— | (2R)-2-(azidomethyl)-2,3-dihydro-1-benzofuran-5-carbaldehyde | —— | C10H9N3O2 |
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