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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—— | 2-[(3S)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]acetic acid | —— | C16H12O4 |
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—— | (2R)-2-[(3R)-3-(4-bromophenyl)-2-oxo-3H-1-benzofuran-5-yl]propanoic acid | —— | C17H13BrO4 |
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—— | (2R)-2-[(3S)-2-oxo-3-phenyl-3H-1-benzofuran-5-yl]propanoic acid | —— | C17H14O4 |
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—— | 3-[1-adamantylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H42N2O5 |
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—— | 3-[benzyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H36N2O7 |
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—— | 3-[benzyl(dodecanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H48N2O7 |
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—— | 8-formyl-3-[hexyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O7 |
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—— | 3-[(2-cyclopentylacetyl)-(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H42N2O7 |
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—— | 3-[(4-fluorophenyl)methyl-(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H33FN2O7 |
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—— | 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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—— | 3-[cycloheptyl(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H36N2O8 |
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—— | 3-[cycloheptyl(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H38N2O8 |
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—— | 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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—— | 3-[butanoyl(oxolan-2-ylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O8 |
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—— | 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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—— | 8-formyl-3-[hexyl-(2-methoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O8 |
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—— | 2-Cyanoethyl-(2,3-dihydro-1-benzofuran-2-ylmethyl)-methylazanium | —— | C13H17N2O+ |
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—— | 3-[furan-3-ylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H28N2O6 |
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—— | 3-[(5E)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid | —— | C18H19NO5S2 |
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—— | 5-[(5E)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid | —— | C20H23NO5S2 |
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—— | 4-[(5E)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid | —— | C19H21NO5S2 |
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—— | methyl (1S,2S,3R,7E,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate | —— | C27H19ClN2O5S |
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—— | methyl (1S,2R,3R,7Z,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate | —— | C27H19ClN2O5S |
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—— | methyl (1S,2S,3R,7Z,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate | —— | C27H19ClN2O5S |
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—— | methyl (1S,2R,3R,7E,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate | —— | C27H19ClN2O5S |
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—— | (2R)-2-methyl-5-[(Z)-2-nitroethenyl]-2,3-dihydro-1-benzofuran | —— | C11H11NO3 |
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—— | (2R)-2-methyl-7-[(Z)-2-nitroethenyl]-2,3-dihydro-1-benzofuran | —— | C11H11NO3 |
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—— | (2S)-2-methyl-5-[(Z)-2-nitroethenyl]-2,3-dihydro-1-benzofuran | —— | C11H11NO3 |
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—— | (2R)-5-methoxy-2-methyl-6-[(Z)-2-nitroethenyl]-2,3-dihydro-1-benzofuran | —— | C12H13NO4 |
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—— | (2E,3S)-2-[(5-chloro-2-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol | —— | C22H17ClO3 |
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—— | (2E,3S)-2-[(3-bromo-5-chloro-2-methoxyphenyl)methylidene]-3H-1-benzofuran-3-ol | —— | C16H12BrClO3 |
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—— | (2E,3R)-2-[(5-chloro-2-phenylmethoxyphenyl)methylidene]-3H-1-benzofuran-3-ol | —— | C22H17ClO3 |
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—— | 3-[benzyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H50N2O7 |
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—— | (Z)-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)prop-2-enenitrile | —— | C21H24N4O2 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[3-methylbutyl(pent-4-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H34N2O5 |
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—— | 3-[(2,4-dichlorophenyl)methyl-(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H28Cl2N2O6 |
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—— | 3-[acetyl-[(4-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H29FN2O7 |
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—— | 3-[(4-fluorophenyl)methyl-(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H31FN2O7 |
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—— | 6-[(Z)-2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-5-nitro-1H-pyrimidine-2,4-dione | —— | C15H13N3O5 |
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—— | 3-[acetyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C22H24N2O6 |
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—— | 3-[3-cyclopentylpropanoyl-[(3,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H38Cl2N2O7 |
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—— | 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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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[(2-methoxyacetyl)-(2-methoxyethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C23H32N2O9 |
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—— | 3-[cyclopentanecarbonyl(2-methoxyethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O8 |
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—— | 3-[3-cyclopentylpropanoyl-[(4-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H35FN2O5 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H35N3O9 |
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—— | 3-[(4-fluorophenyl)methyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H29FN2O6 |
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—— | 3-[cyclopentanecarbonyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H36N2O7 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[3-methoxypropanoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H36N2O9 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-(3-methylbutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H38N2O8 |
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