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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—— | 3-[1-adamantylmethyl(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | 6106-13-4 | C33H42N2O7 |
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—— | 3-[1-adamantylmethyl(pent-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H42N2O7 |
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—— | 3-[1-adamantylmethyl(dodecanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C40H58N2O7 |
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—— | 3-[1-adamantylmethyl(octanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H50N2O7 |
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—— | 3-[1-adamantylmethyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H40N2O8 |
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—— | 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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—— | 3-[1-adamantylmethyl(3-methylbutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H44N2O7 |
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—— | 3-[1-adamantylmethyl(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H42N2O7 |
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—— | 3-[1-adamantylmethyl(butanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H42N2O7 |
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—— | 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[(2R)-2-(4-methoxyphenyl)-2-pyrrolidin-1-ylethyl]acetamide | —— | C23H28N2O3 |
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—— | N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide | —— | C20H20N2O3S |
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—— | (3S)-3-[[(2R)-2-methylbutyl]amino]-2,3-dihydro-1-benzofuran-6-ol | —— | C13H19NO2 |
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—— | (3R)-3-[[(2R)-2-methylbutyl]amino]-2,3-dihydro-1-benzofuran-6-ol | —— | C13H19NO2 |
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—— | 4-amino-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1,2,5-oxadiazole-3-carboxamide | —— | C12H12N4O3 |
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—— | (3S)-3-[2-aminoethyl(methyl)amino]-2,3-dihydro-1-benzofuran-6-ol | —— | C11H16N2O2 |
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—— | (1R)-1-(2,2-dimethyl-3H-1-benzofuran-5-yl)-N,2,2-trimethylbutan-1-amine | —— | C17H27NO |
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—— | (1S)-1-(2,2-dimethyl-3H-1-benzofuran-5-yl)-N,2,2-trimethylbutan-1-amine | —— | C17H27NO |
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—— | (1R)-N-ethyl-2,2-dimethyl-1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]butan-1-amine | —— | C17H27NO |
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—— | [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[(2R)-2-methylpiperazin-1-yl]methanone | —— | C14H18N2O2 |
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—— | (2R,3S)-7-chloro-2,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine | —— | C10H12ClNO |
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—— | (3S)-7-chloro-5-methyl-2,3-dihydro-1-benzofuran-3-amine | —— | C9H10ClNO |
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—— | (3R)-7-chloro-N,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine | —— | C10H12ClNO |
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—— | (3R)-7-chloro-5-methyl-2,3-dihydro-1-benzofuran-3-amine | —— | C9H10ClNO |
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—— | (2S,3R)-7-chloro-2,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine | —— | C10H12ClNO |
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—— | (2R,3S)-7-chloro-N,2,5-trimethyl-2,3-dihydro-1-benzofuran-3-amine | —— | C11H14ClNO |
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—— | (2S,3S)-7-chloro-2,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine | —— | C10H12ClNO |
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—— | (2S,3R)-7-chloro-N,2,5-trimethyl-2,3-dihydro-1-benzofuran-3-amine | —— | C11H14ClNO |
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—— | 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-(3-methylsulfanylpropyl)-1,3-thiazolidin-4-one | —— | C15H19NO2S2 |
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—— | 3-[1-adamantylmethyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C33H42N2O8 |
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—— | (R)-(2,3-difluorophenyl)-(2,3-dihydro-1-benzofuran-5-yl)methanamine | —— | C15H13F2NO |
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—— | (2S)-1-[5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]butan-2-amine | —— | C14H17N3O2 |
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—— | (2S)-3-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-2-methylpropanenitrile | —— | C13H16N2O |
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—— | (2R)-1-[5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]butan-2-amine | —— | C14H17N3O2 |
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—— | (2S)-3-[[(3R)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]amino]-2-methylpropanenitrile | —— | C12H14N2O2 |
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—— | (2R)-1-[5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]butan-2-amine | —— | C14H17N3O2 |
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—— | (2S)-1-[5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]butan-2-amine | —— | C14H17N3O2 |
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—— | (2R)-3-[[(3R)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]amino]-2-methylpropanenitrile | —— | C12H14N2O2 |
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—— | (1S)-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-(2-methoxyphenyl)-1-(1-methylimidazol-2-yl)methanamine | —— | C21H23N3O2 |
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—— | 3-[butanoyl-[(3,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32Cl2N2O7 |
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—— | 3-[3-cyclopentylpropanoyl(2,2,2-trifluoroethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H35F3N2O7 |
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—— | 3-[(3,4-dichlorophenyl)methyl-dodecanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C36H48Cl2N2O7 |
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—— | (2S)-N-[(3R)-1-aminopentan-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C14H20N2O2 |
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—— | (2R)-N-[(3R)-1-aminopentan-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C14H20N2O2 |
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—— | (2S)-N-[(3S)-1-aminopentan-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C14H20N2O2 |
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—— | (2R)-1-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]propan-2-amine | —— | C13H15N3O2 |
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—— | 3-[5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-1,2,4-oxadiazol-3-yl]propan-1-amine | —— | C13H15N3O2 |
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—— | (2R)-N-(3-cyanopropyl)-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C13H14N2O2 |
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—— | (2R)-N-[(4Z)-4-amino-4-hydroxyiminobutyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C13H17N3O3 |
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—— | (2S)-N-(4-amino-4-sulfanylidenebutyl)-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C13H16N2O2S |
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—— | 3-[dodecanoyl-[(2-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C34H45FN2O5 |
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