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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-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea —— C17H21N3O2S
3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea
—— 3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea —— C17H21N3O2S
3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(5-ethyl-1,3-thiazol-2-yl)methyl]-1-methylurea
—— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[[2-(dimethylamino)-1,3-thiazol-4-yl]methyl]urea —— C15H18N4O2S
1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[[2-(dimethylamino)-1,3-thiazol-4-yl]methyl]urea
—— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[[2-(dimethylamino)-1,3-thiazol-4-yl]methyl]urea —— C15H18N4O2S
1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[[2-(dimethylamino)-1,3-thiazol-4-yl]methyl]urea
—— (2R)-5,6-dimethyl-N-(1,2-oxazol-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H16N2O3
(2R)-5,6-dimethyl-N-(1,2-oxazol-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
—— (2S)-5,6-dimethyl-N-(1,2-oxazol-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H16N2O3
(2S)-5,6-dimethyl-N-(1,2-oxazol-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
—— [1-(2,2,2-trifluoroethyl)piperidin-4-yl] (3R)-2,3-dihydro-1-benzofuran-3-carboxylate —— C16H18F3NO3
[1-(2,2,2-trifluoroethyl)piperidin-4-yl] (3R)-2,3-dihydro-1-benzofuran-3-carboxylate
—— [1-(2,2,2-trifluoroethyl)piperidin-4-yl] (3S)-2,3-dihydro-1-benzofuran-3-carboxylate —— C16H18F3NO3
[1-(2,2,2-trifluoroethyl)piperidin-4-yl] (3S)-2,3-dihydro-1-benzofuran-3-carboxylate
—— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1-pyridin-4-ylpyrazol-4-yl)urea —— C18H17N5O2
1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1-pyridin-4-ylpyrazol-4-yl)urea
—— 1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1-pyridin-4-ylpyrazol-4-yl)urea —— C18H17N5O2
1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(1-pyridin-4-ylpyrazol-4-yl)urea
—— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(1-methylimidazol-2-yl)sulfanylacetamide —— C18H23N3O3S
N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(1-methylimidazol-2-yl)sulfanylacetamide
—— 2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C16H20N4O3S2
2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
—— [1-(cyanomethyl)cyclopropyl]methyl (3S)-2,3-dihydro-1-benzofuran-3-carboxylate —— C15H15NO3
[1-(cyanomethyl)cyclopropyl]methyl (3S)-2,3-dihydro-1-benzofuran-3-carboxylate
—— [1-(cyanomethyl)cyclopropyl]methyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate —— C15H15NO3
[1-(cyanomethyl)cyclopropyl]methyl (3R)-2,3-dihydro-1-benzofuran-3-carboxylate
—— (3R)-N-[(1R,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H18N2O3
(3R)-N-[(1R,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— N-[(3R)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-4-methoxypiperidine-1-carboxamide —— C15H18Cl2N2O3
N-[(3R)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-4-methoxypiperidine-1-carboxamide
—— (3R)-N-[(1S,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H18N2O3
(3R)-N-[(1S,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— N-[(3S)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-4-methoxypiperidine-1-carboxamide —— C15H18Cl2N2O3
N-[(3S)-6,7-dichloro-2,3-dihydro-1-benzofuran-3-yl]-4-methoxypiperidine-1-carboxamide
—— (2R)-5-chloro-N-[1-(2-methoxyethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H16ClN3O3
(2R)-5-chloro-N-[1-(2-methoxyethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (3S)-N-[(1R,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H18N2O3
(3S)-N-[(1R,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— (2S)-5-chloro-N-[1-(2-methoxyethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H16ClN3O3
(2S)-5-chloro-N-[1-(2-methoxyethyl)pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (3S)-N-[(1S,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H18N2O3
(3S)-N-[(1S,2S)-2-carbamoylcyclopentyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(5-methyl-1,3-thiazol-2-yl)methyl]urea —— C16H19N3O2S
1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(5-methyl-1,3-thiazol-2-yl)methyl]urea
—— 1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea —— C17H22N4O2
1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea
—— 1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea —— C17H22N4O2
1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[4-(2-methylimidazol-1-yl)butyl]urea
—— 1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(5-methyl-1,3-thiazol-2-yl)methyl]urea —— C16H19N3O2S
1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[(5-methyl-1,3-thiazol-2-yl)methyl]urea
—— 5-amino-1-[(3R)-2,3-dihydro-1-benzofuran-3-carbonyl]pyrazole-4-carbonitrile —— C13H10N4O2
5-amino-1-[(3R)-2,3-dihydro-1-benzofuran-3-carbonyl]pyrazole-4-carbonitrile
—— (3R)-N-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H15NO3S
(3R)-N-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— (3S)-N-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H15NO3S
(3S)-N-[(2S)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— (3S)-N-[(2R)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H19N3O3
(3S)-N-[(2R)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— 5-amino-1-[(3S)-2,3-dihydro-1-benzofuran-3-carbonyl]pyrazole-4-carbonitrile —— C13H10N4O2
5-amino-1-[(3S)-2,3-dihydro-1-benzofuran-3-carbonyl]pyrazole-4-carbonitrile
—— (3S)-N-[(2R)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H15NO3S
(3S)-N-[(2R)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— (3S)-N-[(2S)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H19N3O3
(3S)-N-[(2S)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— (3R)-N-[(2S)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H19N3O3
(3R)-N-[(2S)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— (3R)-N-[(2R)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C15H15NO3S
(3R)-N-[(2R)-2-hydroxy-2-thiophen-2-ylethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— (3R)-N-[(2R)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C16H19N3O3
(3R)-N-[(2R)-2-hydroxy-2-(1-methylpyrazol-4-yl)propyl]-2,3-dihydro-1-benzofuran-3-carboxamide
—— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-fluorophenoxy)acetamide —— C20H22FNO4
N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-fluorophenoxy)acetamide
—— [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]methanone —— C17H20N4O2S
[(3S)-2,3-dihydro-1-benzofuran-3-yl]-[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]methanone
—— [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]methanone —— C17H20N4O2S
[(3R)-2,3-dihydro-1-benzofuran-3-yl]-[4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepan-1-yl]methanone
—— [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(2S)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone —— C18H24N2O3
[(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(2S)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone
—— [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone —— C18H24N2O3
[(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone
—— [(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2S)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone —— C18H24N2O3
[(3R)-2,3-dihydro-1-benzofuran-3-yl]-[(2S)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone
—— [(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone —— C18H24N2O3
[(3S)-2,3-dihydro-1-benzofuran-3-yl]-[(2R)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]methanone
—— 1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2R)-1,4-dimethylpiperazin-2-yl]methyl]urea —— C18H28N4O2
1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2R)-1,4-dimethylpiperazin-2-yl]methyl]urea
—— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2R)-1,4-dimethylpiperazin-2-yl]methyl]urea —— C18H28N4O2
1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2R)-1,4-dimethylpiperazin-2-yl]methyl]urea
—— 1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2S)-1,4-dimethylpiperazin-2-yl]methyl]urea —— C18H28N4O2
1-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2S)-1,4-dimethylpiperazin-2-yl]methyl]urea
—— 1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2S)-1,4-dimethylpiperazin-2-yl]methyl]urea —— C18H28N4O2
1-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-3-[[(2S)-1,4-dimethylpiperazin-2-yl]methyl]urea
—— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide —— C21H25NO6S
N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide
—— (E)-2-(4-chlorophenyl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]ethenesulfonamide —— C20H22ClNO4S
(E)-2-(4-chlorophenyl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]ethenesulfonamide
—— 1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-[(2S)-1-methoxypropan-2-yl]thiourea —— C17H25N3O3S
1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-[(2S)-1-methoxypropan-2-yl]thiourea