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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—— | (2S,3S)-N-[(S)-(2-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C23H25N3O3 |
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—— | (2R,3R)-N-[(S)-(2-fluorophenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C22H22FN3O2 |
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—— | (2S,3R)-2,3-dimethyl-N-[2-(N-methylanilino)ethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C20H24N2O2 |
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—— | (2S,3R)-2,3-dimethyl-N-[(2S)-2-morpholin-4-yl-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C21H26N2O3S |
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—— | (2S,3R)-N-[(2S)-2-(4-ethoxy-3-methoxyphenyl)-2-morpholin-4-ylethyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C26H34N2O5 |
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—— | (2R,3R)-2,3-dimethyl-N-[(2S)-2-morpholin-4-yl-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C21H26N2O3S |
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—— | 3-[cyclopentyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O5 |
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—— | 3-[cycloheptyl(propanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O7 |
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—— | N-[1-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)ethylideneamino]-2-[[5-[1-[2-[1-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)ethylidene]hydrazinyl]-1-oxopropan-2-yl]sulfanyl-1,3,4-thiadiazol-2-yl]sulfanyl]propanamide | —— | C30H34N6O4S3 |
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—— | (2S,3S)-N-[(S)-(4-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C23H25N3O3 |
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—— | (2R,3R)-N-[(S)-(3-fluorophenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C22H22FN3O2 |
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—— | (2S,3R)-2,3-dimethyl-N-[(S)-(1-methylimidazol-2-yl)-phenylmethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C22H23N3O2 |
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—— | (2S,3R)-N-[(S)-(3-fluorophenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C22H22FN3O2 |
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—— | (2S,3R)-N-[(S)-(4-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C23H25N3O3 |
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—— | 3-[(2-fluorophenyl)methyl-pentanoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H33FN2O7 |
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—— | 3-[cycloheptyl(3-methylbutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O7 |
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—— | 3-[cyclohexylmethyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O8 |
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—— | 3-[furan-3-ylmethyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H28N2O7 |
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—— | (1S,2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylcyclopropane-1-carboxamide | —— | C17H23NO3 |
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—— | 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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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(pent-4-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O7 |
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—— | 3-[(2,4-dichlorophenyl)methyl-(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H30Cl2N2O8 |
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—— | (1R,2R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methylcyclopropane-1-carboxamide | —— | C17H23NO3 |
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—— | 3-[cyclopropanecarbonyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H30N2O5 |
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—— | (2S,3R)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C22H25NO4 |
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—— | (2S,3S)-N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2,3-dimethyl-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C22H25NO4 |
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—— | (2R,3R)-2,3-dimethyl-N-[(1R)-1-(4-methylphenyl)-2-morpholin-4-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C24H30N2O3 |
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—— | (2S,3R)-2,3-dimethyl-N-[(1R)-1-(4-methylphenyl)-2-morpholin-4-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C24H30N2O3 |
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—— | (2S,3R)-2,3-dimethyl-N-[(1S)-1-(4-methylphenyl)-2-morpholin-4-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C24H30N2O3 |
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—— | (2R,3R)-2,3-dimethyl-N-[(1S)-1-(4-methylphenyl)-2-morpholin-4-ylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide | —— | C24H30N2O3 |
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—— | 3-[(4-chlorophenyl)methyl-(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31ClN2O7 |
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—— | 3-[cyclohexyl(pent-4-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H36N2O7 |
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—— | 3-[cyclohexyl(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H38N2O7 |
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—— | 3-[cyclopropanecarbonyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H29FN2O5 |
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—— | 3-[cyclopropylmethyl(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C23H30N2O5 |
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—— | 3-[(4-chlorophenyl)methyl-pent-4-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31ClN2O7 |
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—— | 3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H33ClN2O7 |
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—— | 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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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methylpropanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C23H29F3N2O7 |
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—— | 3-[(2-fluorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H29FN2O5 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[pent-4-enoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C24H27F3N2O7 |
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—— | 3-[(4-fluorophenyl)methyl-pentanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H35FN2O7 |
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—— | 3-[cyclopropanecarbonyl-[(2-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H27FN2O5 |
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—— | 3-[furan-3-ylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H30N2O6 |
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—— | 3-[dodecanoyl-[(4-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H47FN2O7 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H38N2O9 |
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—— | 3-[2-(3-fluorophenyl)ethyl-(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H35FN2O8 |
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—— | 3-[cyclopropanecarbonyl-[2-(3-fluorophenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31FN2O7 |
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—— | 3-[(4-chlorophenyl)methyl-(2-ethoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H31ClN2O8 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[(4-methylphenyl)methyl-(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H34N2O8 |
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