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-[6-bromo-2-hydroxy-5-(4-hydroxy-4-methylpent-2-enyl)-5,8a-dimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid | —— | C27H37BrO5 |
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—— | 7-Chloro-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-ol | —— | C11H13ClO3 |
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—— | 3-Hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid | —— | C12H14O5 |
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—— | 7-(8-Hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-1-yl)-4-methoxy-6-methylhepta-2,4,6-trienoic acid | —— | C21H24O5 |
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—— | 5-Methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-6-ol | —— | C12H14O3 |
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—— | 2-(Hydroxymethyl)-5-(2-hydroxy-5-prop-2-enylphenyl)-2,3-dihydro-1-benzofuran-3-ol | —— | C18H18O4 |
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—— | 1-(5-Methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-4-yl)ethanol | —— | C14H18O3 |
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—— | 7-(Hydroxymethyl)-2-(2-hydroxypropan-2-yl)-6-pentyl-2,3-dihydro-1-benzofuran-3-ol | —— | C17H26O4 |
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—— | 6a-hydroxy-3,9-dimethoxypterocarpan | —— | C17H18O5 |
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—— | 2,3-dihydro-2-methylbenzofuran-4-carboxylic acid | 1261963-74-9 | C10H10O3 |
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—— | 6-methoxy-2,3,3-trimethyl-4-phenyl-2H-1-benzofuran | —— | C18H20O2 |
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—— | 3-[2-(2-Hydroxypropan-2-yl)-4-[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy-2,3-dihydro-1-benzofuran-5-yl]propanoic acid | —— | C21H30O9 |
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—— | 2-(1-Acetyloxy-2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid | —— | C14H16O6 |
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—— | 2-[5-(3-Hydroxyprop-1-enyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol | —— | C15H20O4 |
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—— | 1,1,4a,6-tetramethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-6,7-dihydro-3H-furo[3,2-g][1]benzofuran]-2,4',7'-triol | —— | C23H32O5 |
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—— | Methyl 2-[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]acetate | —— | C14H18O4 |
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—— | Ethyl 4-hydroxy-3-(4-hydroxyphenyl)-2-[[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-oxofuran-2-carboxylate | —— | C25H26O8 |
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—— | 2-Prop-1-en-2-yl-2,3-dihydro-1-benzofuran-6-ol | —— | C11H12O2 |
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—— | 2-(2-Hydroxy-6-methylhept-5-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid | —— | C17H22O4 |
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—— | 3-Hydroxy-2-(1,2,3-trihydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carbaldehyde | —— | C12H14O6 |
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—— | 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[3-(morpholin-4-yl)propyl]-1H-pyrazole-3-carboxamide | —— | C19H24N4O3 |
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—— | 2-Hydroxy-1-[4-hydroxy-7-(3-methylbut-2-enyl)-2-(3,3,5-trimethylhex-4-enyl)-2,3-dihydro-1-benzofuran-5-yl]ethanone | —— | C24H34O4 |
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—— | 2-[5-(Hydroxymethyl)-2,3-dihydro-1-benzofuran-2-yl]propane-1,2-diol | —— | C12H16O4 |
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—— | 2,3-Dihydro-N-[2-(1H-imidazol-5-yl)ethyl]-6-benzofuranacetamide | —— | C15H17N3O2 |
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—— | Methyl 7-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylate | —— | C13H16O5 |
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—— | 3,3a-Dimethyl-3,8b-dihydrocyclopenta[b][1]benzofuran | —— | C13H14O |
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—— | Methyl 3-(3-(2-(2,3-dihydrobenzofuran-5-yl)ethoxy)-4-methoxyphenyl)-3-(1-(3,4-dihydroxyphenethyl)-4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)propanoate | —— | C35H37NO9 |
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—— | 9-Methoxy-11-oxatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene | —— | C17H20O2 |
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—— | N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-2-[2-(4-methoxyphenyl)-5-methyl-7-oxo-7H-furo[3,2-b]pyran-3-yl]acetamide | —— | C26H23NO6 |
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—— | 3-Hydroxy-2-(2-hydroxypropan-2-yl)-7-(3-methylbut-2-enyl)-2,3-dihydro-1-benzofuran-5-carboxylic acid | —— | C17H22O5 |
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—— | 2-(2,3-dihydro-1-benzofuran-6-yl)-N-{[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}acetamide | —— | C23H27NO4 |
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—— | 2-[6-bromo-2-hydroxy-5,8a-dimethyl-5-(4-methyl-3-oxopent-4-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid | —— | C27H35BrO5 |
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—— | 1-(2-Prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)propane-1,2-diol | —— | C14H18O3 |
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—— | 2-[6-bromo-2-hydroxy-5,8a-dimethyl-5-(4-methylpent-3-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]-2,3-dihydro-1-benzofuran-5-carboxylic acid | —— | C27H37BrO4 |
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—— | 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-(4-hydroxyphenyl)ethyl]-1H-pyrazole-3-carboxamide | —— | C20H19N3O3 |
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—— | 3-[5-(3-Methoxybuta-1,3-dienyl)-2,3-dihydro-1-benzofuran-2-yl]pentan-3-ol | —— | C18H24O3 |
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—— | methyl 2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carboxylate | —— | C13H14O3 |
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—— | 1-[5-Hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-2-methylpropan-1-one | —— | C15H20O4 |
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—— | Methyl 3-(2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)prop-2-enoate | —— | C15H16O3 |
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—— | 1-[3-(3-Methylbutanoyloxy)-2-(3-oxoprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethyl 2-methylbutanoate | —— | C23H30O6 |
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—— | 1-[2-(3-Oxoprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethyl 2-methylbut-2-enoate | —— | C18H20O4 |
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—— | methyl3-[5-[2-(2,3-dihydro-1-benzofuran-5-yl)ethoxy]-4-methoxycyclohepta-1,3,6-trien-1-yl]-3-[2-[6,7-dihydroxy-4-(4,5-dihydroxycyclohexa-1,3-dien-1-yl)cyclohexa-1,5-dien-1-yl]ethyl-hydroxy-5-oxo-1-azacyclohepta-3,6-dien-4-yl]propanoate | —— | C35H37NO9 |
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—— | 2-(5-Formyl-2,3-dihydro-1-benzofuran-2-yl)prop-2-enyl 2-methylpropanoate | —— | C16H18O4 |
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—— | 4-(2-hydroxy-5,7-dimethyl-3H-1-benzofuran-2-yl)piperidine-2,6-dione | —— | C15H17NO4 |
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—— | 2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carbaldehyde | 69745-01-3 | C12H12O2 |
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—— | [2-(Hydroxymethyl)-6-[3-(hydroxymethyl)-2-methoxy-2,3-dihydro-1-benzofuran-6-yl]-2,3-dihydro-1-benzofuran-3-yl]methanol | —— | C20H22O6 |
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—— | 2-Hydroxy-1-(2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl)propan-1-one | —— | C14H16O3 |
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—— | 1-[7-(Hydroxymethyl)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]propane-1,2-diol | —— | C15H22O5 |
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—— | methyl 2-methyl-2,3-dihydrobenzofuran-7-carboxylate | 41176-57-2 | C11H12O3 |
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—— | 2-(2,3-Dihydro-1-benzofuran-6-YL)-N-[3-(morpholin-4-YL)propyl]acetamide | —— | C17H24N2O3 |
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