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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—— | (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-[(4-methyl-1,2,4-triazol-3-yl)methyl]ethanamine | —— | C14H18N4O |
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—— | (3R)-3-[(4-methyl-1,2,4-triazol-3-yl)methylamino]-2,3-dihydro-1-benzofuran-6-ol | —— | C12H14N4O2 |
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—— | (2R)-N-(1H-pyrazol-4-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C13H13N3O2 |
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—— | (2S)-N-(1H-pyrazol-4-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C13H13N3O2 |
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—— | (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(1H-pyrazol-4-ylmethyl)ethanamine | —— | C14H17N3O |
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—— | (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(1H-pyrazol-4-ylmethyl)ethanamine | —— | C14H17N3O |
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—— | (3R)-3-(1H-pyrazol-4-ylmethylamino)-2,3-dihydro-1-benzofuran-6-ol | —— | C12H13N3O2 |
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—— | 1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-N-(1H-pyrazol-4-ylmethyl)methanamine | —— | C16H21N3O2 |
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—— | (3S)-3-(1H-pyrazol-4-ylmethylamino)-2,3-dihydro-1-benzofuran-6-ol | —— | C12H13N3O2 |
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—— | 1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-N-(1H-pyrazol-4-ylmethyl)methanamine | —— | C16H21N3O2 |
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—— | N-[(1S)-1-(5-bromothiophen-2-yl)ethyl]-2,3-dihydro-1-benzofuran-5-amine | —— | C14H14BrNOS |
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—— | N-[(1R)-1-(5-bromothiophen-2-yl)ethyl]-2,3-dihydro-1-benzofuran-5-amine | —— | C14H14BrNOS |
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—— | 1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(4,5-dimethyl-1,2,4-triazol-3-yl)methyl]methanamine | —— | C14H18N4O |
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—— | 1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[(4,5-dimethyl-1,2,4-triazol-3-yl)methyl]methanamine | —— | C14H18N4O |
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—— | N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1H-pyrazole-4-carboxamide | —— | C13H13N3O2 |
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—— | 1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-(furan-2-ylmethyl)methanamine | —— | C14H15NO2 |
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—— | 2-[[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]amino]-6-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide | —— | C22H26N2O4S |
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—— | 4-bromo-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylpyrrole-2-carboxamide | —— | C15H15BrN2O2 |
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—— | 3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylamino]propanenitrile | —— | C12H14N2O |
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—— | 3-[[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methylamino]methyl]benzonitrile | —— | C17H16N2O |
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—— | 3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methylamino]propanenitrile | —— | C12H14N2O |
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—— | 1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-(thiophen-2-ylmethyl)methanamine | —— | C14H15NOS |
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—— | 1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-(thiophen-2-ylmethyl)methanamine | —— | C14H15NOS |
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—— | 3-[cyclopropanecarbonyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C27H37N3O8 |
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—— | 4-bromo-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-methylpyrrole-2-carboxamide | —— | C15H15BrN2O2 |
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—— | N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylpropan-1-amine | —— | C13H19NO |
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—— | 1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[(3-methylthiophen-2-yl)methyl]methanamine | —— | C15H17NOS |
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—— | 1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(3-methylthiophen-2-yl)methyl]methanamine | —— | C15H17NOS |
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—— | 1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(4-fluorophenyl)methyl]methanamine | —— | C16H16FNO |
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—— | 3-[cycloheptyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O5 |
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—— | 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(oxolane-3-carbonyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H37N3O9 |
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—— | 3-[acetyl(cycloheptyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C26H34N2O7 |
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—— | 3-[cyclohexylmethyl(3-cyclopentylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C32H46N2O7 |
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—— | 2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,3-thiazole-4-carbaldehyde | —— | C15H15NO3S |
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—— | 3-[cyclopentyl(3-cyclopentylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H38N2O5 |
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—— | N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2,2,2-trifluoroethanamine | —— | C11H12F3NO |
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—— | 3-[cycloheptyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C29H40N2O5 |
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—— | 3-[(2-cyclopentylacetyl)-(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C30H43N3O8 |
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—— | (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2,2,2-trifluoroethylamino)acetonitrile | —— | C12H11F3N2O |
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—— | 3-[1-adamantylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C31H40N2O5 |
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—— | (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2,2,2-trifluoroethylamino)acetonitrile | —— | C12H11F3N2O |
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—— | (3S)-6-hydroxy-3-(2,2,2-trifluoroethylamino)-2H-1-benzofuran-3-carbonitrile | —— | C11H9F3N2O2 |
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—— | (3R)-6-hydroxy-3-(2,2,2-trifluoroethylamino)-2H-1-benzofuran-3-carbonitrile | —— | C11H9F3N2O2 |
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—— | (2R)-2-(cycloheptylamino)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile | —— | C17H22N2O |
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—— | (3R)-3-(cycloheptylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile | —— | C16H20N2O2 |
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—— | 4-hydroxy-N-(2-hydroxyethyl)-3-[3-methylbut-2-enoyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C25H32N2O6 |
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—— | (2S)-2-(cyclohexylamino)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile | —— | C16H20N2O |
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—— | (3R)-3-(cyclohexylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile | —— | C15H18N2O2 |
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—— | (3S)-3-(cyclohexylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile | —— | C15H18N2O2 |
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—— | (2R)-2-(cyclohexylamino)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile | —— | C16H20N2O |
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