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-((2,3-dihydrobenzofuran-5-yl)sulfonyl)piperidin-4-yl)methyl)-4-(thiophen-2-yl)-1H-1,2,4-triazol-5(4H)-one | —— | C20H22N4O4S2 |
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—— | 3-((1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)-N,N-dimethylpyrazin-2-amine | —— | C19H24N4O4S |
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—— | 2-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)-6-methoxypyrazine | —— | C18H21N3O5S |
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—— | 2-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)-3-methoxypyrazine | —— | C18H21N3O5S |
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—— | 6-((1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)-N,N-dimethylpyridazin-3-amine | —— | C19H24N4O4S |
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—— | 3-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)-6-methoxypyridazine | —— | C18H21N3O5S |
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—— | 3-((1-(2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetyl)pyrrolidin-3-yl)oxy)pyrazine-2-carbonitrile | —— | C21H22N4O4 |
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—— | N-((1r,4r)-4-((3-cyanopyrazin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C19H20N4O4S |
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—— | N-((1r,4r)-4-((6-methoxypyrazin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C19H23N3O5S |
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—— | N-((1r,4r)-4-((3-cyanopyrazin-2-yl)oxy)cyclohexyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide | —— | C23H26N4O4 |
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—— | 2,2,4-Trimethyl-2,3-dihydro-1-benzofuran-7-carbonitrile | —— | C12H13NO |
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—— | N-((1r,4r)-4-((3-methoxypyrazin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C19H23N3O5S |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-((6-methoxypyrazin-2-yl)oxy)cyclohexyl)acetamide | —— | C23H29N3O5 |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-((3-methoxypyrazin-2-yl)oxy)cyclohexyl)acetamide | —— | C23H29N3O5 |
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—— | 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-(pyridin-3-ylmethyl)-1,3-thiazinan-4-one | —— | C18H18N2O2S |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-(pyrazin-2-yloxy)cyclohexyl)acetamide | —— | C22H27N3O4 |
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—— | N-((1r,4r)-4-((5-methylpyridin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C20H24N2O4S |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-((5-methylpyridin-2-yl)oxy)cyclohexyl)acetamide | —— | C24H30N2O4 |
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—— | N-((1r,4r)-4-((5-cyanopyridin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C20H21N3O4S |
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—— | N-((1r,4r)-4-((5-chloropyridin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C19H21ClN2O4S |
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—— | N-((1r,4r)-4-((5-cyanopyridin-2-yl)oxy)cyclohexyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide | —— | C24H27N3O4 |
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—— | N-((1r,4r)-4-((5-chloropyridin-2-yl)oxy)cyclohexyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide | —— | C23H27ClN2O4 |
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—— | N-((1r,4r)-4-((5-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C20H21F3N2O4S |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-((5-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)acetamide | —— | C24H27F3N2O4 |
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—— | N-((1r,4r)-4-(pyridin-2-yloxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C19H22N2O4S |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-(pyridin-2-yloxy)cyclohexyl)acetamide | —— | C23H28N2O4 |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((6-(furan-2-yl)pyridin-3-yl)methyl)acetamide | —— | C22H22N2O4 |
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—— | 1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-2-(trifluoromethyl)piperidine | —— | C14H16F3NO3S |
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—— | 3-Butyl-2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazolidin-4-one | —— | C15H19NO2S |
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—— | N-(octahydrobenzo[b][1,4]dioxin-6-yl)-2,3-dihydrobenzofuran-5-sulfonamide | —— | C16H21NO5S |
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—— | 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(octahydrobenzo[b][1,4]dioxin-6-yl)acetamide | —— | C20H27NO5 |
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—— | 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-[2-(2-hydroxyethylsulfanyl)ethyl]-1,3-thiazolidin-4-one | —— | C15H19NO3S2 |
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—— | 2-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)-5-methylpyridine | —— | C18H20N2O4S |
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—— | 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-(pyridin-4-yloxy)pyrrolidin-1-yl)ethanone | —— | C21H24N2O4 |
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—— | N-[(E)-(2-fluorophenyl)methylidene]-2,2,4-trimethyl-2,3-dihydro-1-benzofuran-7-amine | —— | C18H18FNO |
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—— | 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-((4-(trifluoromethyl)pyridin-2-yl)oxy)pyrrolidin-1-yl)ethanone | —— | C22H23F3N2O4 |
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—— | 2-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)isonicotinonitrile | —— | C18H17N3O4S |
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—— | N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-6-morpholin-4-yl-5-nitropyrimidin-4-amine | —— | C17H19N5O4 |
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—— | 2-((1-(2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetyl)pyrrolidin-3-yl)oxy)isonicotinonitrile | —— | C22H23N3O4 |
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—— | 5-Bromo-2-((1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)pyridine | —— | C17H17BrN2O4S |
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—— | 1-(3-((5-Bromopyridin-2-yl)oxy)pyrrolidin-1-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)ethanone | —— | C21H23BrN2O4 |
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—— | 3-Bromo-2-((1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)pyridine | —— | C17H17BrN2O4S |
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—— | 2-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)-6-methylpyridine | —— | C18H20N2O4S |
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—— | 1-(3-((3-Bromopyridin-2-yl)oxy)pyrrolidin-1-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)ethanone | —— | C21H23BrN2O4 |
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—— | 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-((6-methylpyridin-2-yl)oxy)pyrrolidin-1-yl)ethanone | —— | C22H26N2O4 |
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—— | 3-[(3,4-dichlorophenyl)methyl-(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C28H32Cl2N2O8 |
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—— | 2-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)pyridine | —— | C17H18N2O4S |
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—— | 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-(pyridin-2-yloxy)pyrrolidin-1-yl)ethanone | —— | C21H24N2O4 |
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—— | 3-[cycloheptyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide | —— | C34H52N2O5 |
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—— | 2-chloro-N-(2,2,4-trimethyl-2,3-dihydro-1-benzofuran-7-yl)acetamide | —— | C13H16ClNO2 |
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