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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
—— 2-[6-[[3-(4,6-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C27H26O5
2-[6-[[3-(4,6-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-[6-[[3-[2,2-bis(methoxymethyl)-4,6-dimethyl-3H-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C31H34O7
2-[6-[[3-[2,2-bis(methoxymethyl)-4,6-dimethyl-3H-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-[(3S)-6-[[3-(3,3,4,6-tetramethyl-2H-1-benzofuran-5-yl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C29H30O5
2-[(3S)-6-[[3-(3,3,4,6-tetramethyl-2H-1-benzofuran-5-yl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-[6-[[3-[2-(Methoxymethyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C29H30O6
2-[6-[[3-[2-(Methoxymethyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-[6-[[3-[3-(2-Methoxyethoxy)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C30H32O7
2-[6-[[3-[3-(2-Methoxyethoxy)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-[(3S)-6-[[3-(3-methoxy-2,2,4,6-tetramethyl-3H-1-benzofuran-5-yl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C30H32O6
2-[(3S)-6-[[3-(3-methoxy-2,2,4,6-tetramethyl-3H-1-benzofuran-5-yl)phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-[(3S)-6-[[3-[2,2-bis(hydroxymethyl)-4,6-dimethyl-3H-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C29H30O7
2-[(3S)-6-[[3-[2,2-bis(hydroxymethyl)-4,6-dimethyl-3H-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-[(3S)-6-[[3-[2,2-bis(ethoxymethyl)-4,6-dimethyl-3H-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid —— C33H38O7
2-[(3S)-6-[[3-[2,2-bis(ethoxymethyl)-4,6-dimethyl-3H-1-benzofuran-5-yl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
—— 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-((6-(dimethylamino)pyridazin-3-yl)oxy)pyrrolidin-1-yl)ethanone —— C22H28N4O4
2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-((6-(dimethylamino)pyridazin-3-yl)oxy)pyrrolidin-1-yl)ethanone
—— 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-((6-(dimethylamino)pyrazin-2-yl)oxy)pyrrolidin-1-yl)ethanone —— C22H28N4O4
2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-((6-(dimethylamino)pyrazin-2-yl)oxy)pyrrolidin-1-yl)ethanone
—— N-((1r,4r)-4-((4,6-dimethylpyrimidin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C20H25N3O4S
N-((1r,4r)-4-((4,6-dimethylpyrimidin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-((4,6-dimethylpyrimidin-2-yl)oxy)cyclohexyl)acetamide —— C24H31N3O4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-((4,6-dimethylpyrimidin-2-yl)oxy)cyclohexyl)acetamide
—— N-((1r,4r)-4-((5-chloropyrimidin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C18H20ClN3O4S
N-((1r,4r)-4-((5-chloropyrimidin-2-yl)oxy)cyclohexyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— N-((1r,4r)-4-((5-chloropyrimidin-2-yl)oxy)cyclohexyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C22H26ClN3O4
N-((1r,4r)-4-((5-chloropyrimidin-2-yl)oxy)cyclohexyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-(pyrimidin-2-yloxy)cyclohexyl)acetamide —— C22H27N3O4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1r,4r)-4-(pyrimidin-2-yloxy)cyclohexyl)acetamide
—— 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(7-(thiophen-2-yl)-1,4-thiazepan-4-yl)ethanone —— C21H25NO3S2
2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(7-(thiophen-2-yl)-1,4-thiazepan-4-yl)ethanone
—— 4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-(furan-2-yl)-1,4-thiazepane —— C17H19NO4S2
4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-(furan-2-yl)-1,4-thiazepane
—— 7-(2,5-Difluorophenyl)-4-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-1,4-thiazepane —— C19H19F2NO3S2
7-(2,5-Difluorophenyl)-4-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-1,4-thiazepane
—— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(5-ethyl-1,3,4-thiadiazol-2-yl)acetamide —— C16H19N3O3S
2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(5-ethyl-1,3,4-thiadiazol-2-yl)acetamide
—— 4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-(o-tolyl)-1,4-thiazepane —— C20H23NO3S2
4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-(o-tolyl)-1,4-thiazepane
—— 1-(7-(2,5-Difluorophenyl)-1,4-thiazepan-4-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)ethanone —— C23H25F2NO3S
1-(7-(2,5-Difluorophenyl)-1,4-thiazepan-4-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)ethanone
—— 4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-(2-fluorophenyl)-1,4-thiazepane —— C19H20FNO3S2
4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-(2-fluorophenyl)-1,4-thiazepane
—— 4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-phenyl-1,4-thiazepane —— C19H21NO3S2
4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)-7-phenyl-1,4-thiazepane
—— 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(7-phenyl-1,4-thiazepan-4-yl)ethanone —— C23H27NO3S
2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(7-phenyl-1,4-thiazepan-4-yl)ethanone
—— N-(2-hydroxy-3-(2-oxopyridin-1(2H)-yl)propyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C16H18N2O5S
N-(2-hydroxy-3-(2-oxopyridin-1(2H)-yl)propyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(((1R,3S,5r,7r)-2-methoxyadamantan-2-yl)methyl)acetamide —— C24H33NO4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(((1R,3S,5r,7r)-2-methoxyadamantan-2-yl)methyl)acetamide
—— N-(2-(2-chlorophenyl)-2-methoxyethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C21H24ClNO4
N-(2-(2-chlorophenyl)-2-methoxyethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
—— N-(2-methoxy-2-(3-methoxyphenyl)ethyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C18H21NO5S
N-(2-methoxy-2-(3-methoxyphenyl)ethyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(2-(3-fluorophenyl)-2-methoxyethyl)acetamide —— C21H24FNO4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(2-(3-fluorophenyl)-2-methoxyethyl)acetamide
—— N-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-4-yl)-2,3-dihydrobenzofuran-5-sulfonamide —— C17H21N3O4S
N-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-4-yl)-2,3-dihydrobenzofuran-5-sulfonamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-4-yl)acetamide —— C21H27N3O4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-4-yl)acetamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1-(thiazol-2-yl)piperidin-3-yl)methyl)acetamide —— C21H27N3O3S
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1-(thiazol-2-yl)piperidin-3-yl)methyl)acetamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1-(thiazol-2-yl)pyrrolidin-2-yl)methyl)acetamide —— C20H25N3O3S
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((1-(thiazol-2-yl)pyrrolidin-2-yl)methyl)acetamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(2-(3-(trifluoromethyl)-6,7-dihydropyrano[4,3-c]pyrazol-1(4H)-yl)ethyl)acetamide —— C21H24F3N3O4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(2-(3-(trifluoromethyl)-6,7-dihydropyrano[4,3-c]pyrazol-1(4H)-yl)ethyl)acetamide
—— N-(2-(6,7-dihydropyrano[4,3-c]pyrazol-1(4H)-yl)ethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C20H25N3O4
N-(2-(6,7-dihydropyrano[4,3-c]pyrazol-1(4H)-yl)ethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
—— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]ethyl]acetamide —— C22H26F3N3O3
2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]ethyl]acetamide
—— N-[2-(3-pyridin-4-yl-4,5,6,7-tetrahydroindazol-1-yl)ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C22H24N4O3S
N-[2-(3-pyridin-4-yl-4,5,6,7-tetrahydroindazol-1-yl)ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((5-(furan-2-carbonyl)thiophen-2-yl)methyl)acetamide —— C22H21NO5S
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((5-(furan-2-carbonyl)thiophen-2-yl)methyl)acetamide
—— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(oxan-4-yl)-N-(thiophen-2-ylmethyl)acetamide —— C22H27NO4S
2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(oxan-4-yl)-N-(thiophen-2-ylmethyl)acetamide
—— 2-[(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-1-[4-(2-phenylethenesulfonyl)piperazin-1-yl]ethan-1-one —— C24H28N2O5S
2-[(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-1-[4-(2-phenylethenesulfonyl)piperazin-1-yl]ethan-1-one
—— 1-(2-benzylimino-1,3-thiazolidin-3-yl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethanone —— C22H24N2O3S
1-(2-benzylimino-1,3-thiazolidin-3-yl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethanone
—— 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-(4-fluorophenyl)azepan-1-yl)ethanone —— C24H28FNO3
2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(3-(4-fluorophenyl)azepan-1-yl)ethanone
—— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-(3-methyl-1,2,4-oxadiazol-5-yl)thiophen-3-yl]acetamide —— C19H19N3O4S
2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-(3-methyl-1,2,4-oxadiazol-5-yl)thiophen-3-yl]acetamide
—— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[2-(2-phenylethylimino)-1,3-thiazolidin-3-yl]ethanone —— C23H26N2O3S
2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-1-[2-(2-phenylethylimino)-1,3-thiazolidin-3-yl]ethanone
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(3-(furan-2-yl)-2-hydroxy-2-methylpropyl)acetamide —— C20H25NO5
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(3-(furan-2-yl)-2-hydroxy-2-methylpropyl)acetamide
—— N-(5-cyanothiazol-2-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C16H15N3O3S
N-(5-cyanothiazol-2-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
—— 2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(4-(2-hydroxy-2-(thiophen-2-yl)ethyl)piperazin-1-yl)ethanone —— C22H28N2O4S
2-((2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-1-(4-(2-hydroxy-2-(thiophen-2-yl)ethyl)piperazin-1-yl)ethanone
—— N-(2-(3-chlorophenyl)-2-methoxypropyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C18H20ClNO4S
N-(2-(3-chlorophenyl)-2-methoxypropyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— N-(2-(3-chlorophenyl)-2-methoxypropyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C22H26ClNO4
N-(2-(3-chlorophenyl)-2-methoxypropyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(2-methoxy-2-phenylbutyl)acetamide —— C23H29NO4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(2-methoxy-2-phenylbutyl)acetamide