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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
—— 1-(3-Ethoxyspiro[3.3]heptan-1-yl)-3-(5-methyl-2,3-dihydro-1-benzofuran-3-yl)urea —— C19H26N2O3
1-(3-Ethoxyspiro[3.3]heptan-1-yl)-3-(5-methyl-2,3-dihydro-1-benzofuran-3-yl)urea
—— N-[(3,4-diethyl-6-oxo-1H-pyridazin-5-yl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide —— C18H23N3O4S
N-[(3,4-diethyl-6-oxo-1H-pyridazin-5-yl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5-sulfonamide
—— 1-(5-Methyl-2,3-dihydro-1-benzofuran-3-yl)-3-(2-methyl-2-methylsulfonylpropyl)urea —— C15H22N2O4S
1-(5-Methyl-2,3-dihydro-1-benzofuran-3-yl)-3-(2-methyl-2-methylsulfonylpropyl)urea
—— 3-[2-(3-fluorophenyl)ethyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H35FN2O7
3-[2-(3-fluorophenyl)ethyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopropylmethyl(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H32N2O8
3-[cyclopropylmethyl(3-methoxypropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl]acetamide —— C15H16N2O4S2
2-(2,3-dihydro-1-benzofuran-5-yl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl]acetamide
—— 1-(2,3-dihydro-1-benzofuran-5-yl)-3-[(4-methyl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]urea —— C13H15N5O2S
1-(2,3-dihydro-1-benzofuran-5-yl)-3-[(4-methyl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]urea
—— 5,6-dimethyl-N-(2-oxopiperidin-1-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H20N2O3
5,6-dimethyl-N-(2-oxopiperidin-1-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
—— (5Z)-5-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one —— C18H20N2O3S
(5Z)-5-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one
—— 3-[1-adamantylmethyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H38N2O5
3-[1-adamantylmethyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— N-[(5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-4-methylcyclohexan-1-amine —— C18H27NO2
N-[(5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-4-methylcyclohexan-1-amine
—— 3-[cyclopentyl-(2-cyclopentylacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H38N2O7
3-[cyclopentyl-(2-cyclopentylacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (5E)-2-cyclopentylimino-5-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methylidene]-1,3-thiazolidin-4-one —— C19H22N2O2S
(5E)-2-cyclopentylimino-5-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methylidene]-1,3-thiazolidin-4-one
—— 6-(2,3-Dihydro-1-benzofuran-5-ylmethylcarbamoyl)cyclohex-3-ene-1-carboxylic acid —— C17H19NO4
6-(2,3-Dihydro-1-benzofuran-5-ylmethylcarbamoyl)cyclohex-3-ene-1-carboxylic acid
—— 3-[cyclopentyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H44N2O7
3-[cyclopentyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]-1H-pyrazole-3-carboxamide —— C15H11F3N6O2
5-(2,3-dihydro-1-benzofuran-5-yl)-N-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]-1H-pyrazole-3-carboxamide
—— 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[5-(propan-2-yl)-1H-1,2,4-triazol-3-yl]-1H-pyrazole-3-carboxamide —— C17H18N6O2
5-(2,3-dihydro-1-benzofuran-5-yl)-N-[5-(propan-2-yl)-1H-1,2,4-triazol-3-yl]-1H-pyrazole-3-carboxamide
—— 5-(2,3-dihydro-1-benzofuran-5-yl)-N-(5-ethyl-1H-1,2,4-triazol-3-yl)-1H-pyrazole-3-carboxamide —— C16H16N6O2
5-(2,3-dihydro-1-benzofuran-5-yl)-N-(5-ethyl-1H-1,2,4-triazol-3-yl)-1H-pyrazole-3-carboxamide
—— 3-[(2-ethoxyacetyl)-(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H38N2O8
3-[(2-ethoxyacetyl)-(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-(2,3-dihydro-1-benzofuran-5-yl)-N-[6-(trifluoromethyl)pyridin-3-yl]-1H-pyrazole-5-carboxamide —— C18H13F3N4O2
3-(2,3-dihydro-1-benzofuran-5-yl)-N-[6-(trifluoromethyl)pyridin-3-yl]-1H-pyrazole-5-carboxamide
—— 3-(2,3-dihydro-1-benzofuran-5-yl)-N-(1,1-dioxidotetrahydrothiophen-3-yl)propanamide —— C15H19NO4S
3-(2,3-dihydro-1-benzofuran-5-yl)-N-(1,1-dioxidotetrahydrothiophen-3-yl)propanamide
—— 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[(2S)-1-hydroxy-3-methylpentan-2-yl]acetamide —— C16H23NO3
2-(2,3-dihydro-1-benzofuran-5-yl)-N-[(2S)-1-hydroxy-3-methylpentan-2-yl]acetamide
—— 2-(2,3-Dihydro-1-benzofuran-5-YL)-N-[(2S)-1-hydroxy-4-(methylsulfanyl)butan-2-YL]acetamide —— C15H21NO3S
2-(2,3-Dihydro-1-benzofuran-5-YL)-N-[(2S)-1-hydroxy-4-(methylsulfanyl)butan-2-YL]acetamide
—— 3-methoxy-3-(4-nitrophenyl)-2H-1-benzofuran —— C15H13NO4
3-methoxy-3-(4-nitrophenyl)-2H-1-benzofuran
—— 3-[3-ethoxypropyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H42N2O6
3-[3-ethoxypropyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O9
4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopentyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H32N2O5
3-[cyclopentyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[(2,4-dichlorophenyl)methyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H36Cl2N2O7
3-[(2,4-dichlorophenyl)methyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclohexylmethyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H38N2O8
3-[cyclohexylmethyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— N-((5-(thiophen-2-yl)pyridin-3-yl)methyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C18H16N2O3S2
N-((5-(thiophen-2-yl)pyridin-3-yl)methyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— N-(2-(5-chlorothiophen-2-yl)-2-methoxyethyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C15H16ClNO4S2
N-(2-(5-chlorothiophen-2-yl)-2-methoxyethyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— N-(2-(5-chlorothiophen-2-yl)-2-methoxyethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C19H22ClNO4S
N-(2-(5-chlorothiophen-2-yl)-2-methoxyethyl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
—— 3-[1-adamantylmethyl-(2-ethoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C32H44N2O8
3-[1-adamantylmethyl-(2-ethoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((2-(thiophen-3-yl)pyridin-3-yl)methyl)acetamide —— C22H22N2O3S
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-((2-(thiophen-3-yl)pyridin-3-yl)methyl)acetamide
—— N-((2-(thiophen-3-yl)pyridin-3-yl)methyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C18H16N2O3S2
N-((2-(thiophen-3-yl)pyridin-3-yl)methyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— N-(2-(2,4-dioxooxazolidin-3-yl)-1-phenylethyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C19H18N2O6S
N-(2-(2,4-dioxooxazolidin-3-yl)-1-phenylethyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— 1-((1-(1-(2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetyl)azetidin-3-yl)-1H-1,2,3-triazol-4-yl)methyl)pyrrolidin-2-one —— C22H27N5O4
1-((1-(1-(2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetyl)azetidin-3-yl)-1H-1,2,3-triazol-4-yl)methyl)pyrrolidin-2-one
—— N-(pyridin-3-yl(tetrahydro-2H-pyran-4-yl)methyl)-2,3-dihydrobenzofuran-5-sulfonamide —— C19H22N2O4S
N-(pyridin-3-yl(tetrahydro-2H-pyran-4-yl)methyl)-2,3-dihydrobenzofuran-5-sulfonamide
—— 3-[cyclopropanecarbonyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H32N2O6
3-[cyclopropanecarbonyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperazin-1-yl)(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)methanone —— C20H24N4O4S
(4-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperazin-1-yl)(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)methanone
—— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-methylpropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H36N2O6
4-hydroxy-N-(2-hydroxyethyl)-3-[2-methylpropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(pyridin-3-yl(tetrahydro-2H-pyran-4-yl)methyl)acetamide —— C23H28N2O4
2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(pyridin-3-yl(tetrahydro-2H-pyran-4-yl)methyl)acetamide
—— 3-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)pyrazine-2-carbonitrile —— C18H18N4O4S
3-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)pyrazine-2-carbonitrile
—— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[oxolan-2-ylmethyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H32N2O8
8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[oxolan-2-ylmethyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-pentanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H36N2O6
4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-pentanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)-6-methylpyridazine —— C18H21N3O4S
3-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)-6-methylpyridazine
—— 3-[cyclopentyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H40N2O7
3-[cyclopentyl-(2-cyclopentylacetyl)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)piperidin-3-yl)oxy)pyrazine —— C17H19N3O4S
2-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)piperidin-3-yl)oxy)pyrazine
—— 6-((1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)-N,N-dimethylpyridazin-3-amine —— C18H22N4O4S
6-((1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)-N,N-dimethylpyridazin-3-amine
—— 3-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)-6-methoxypyridazine —— C17H19N3O5S
3-((1-((2,3-Dihydrobenzofuran-5-yl)sulfonyl)pyrrolidin-3-yl)oxy)-6-methoxypyridazine