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香豆素

香豆素 基本信息

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