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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-[3-cyclopentylpropanoyl(3-methylbutyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H42N2O7
3-[3-cyclopentylpropanoyl(3-methylbutyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclohexyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H40N2O7
3-[cyclohexyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclohexyl(dodecanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C35H52N2O7
3-[cyclohexyl(dodecanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[2-(3-fluorophenyl)ethyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H31FN2O6
3-[2-(3-fluorophenyl)ethyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[butanoyl(furan-3-ylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H30N2O8
3-[butanoyl(furan-3-ylmethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopropylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H32N2O5
3-[cyclopropylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 2-[6-methyl-4-(methylaminomethyl)-7-[(E)-1-methyliminopent-2-en-2-yl]oxy-5-[1-(4-methylphenyl)azepan-4-yl]-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol —— C33H47N3O3
2-[6-methyl-4-(methylaminomethyl)-7-[(E)-1-methyliminopent-2-en-2-yl]oxy-5-[1-(4-methylphenyl)azepan-4-yl]-2,3-dihydro-1-benzofuran-2-yl]propan-2-ol
—— 3-[hexyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H42N2O8
3-[hexyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[3-cyclopentylpropanoyl-[2-(3-methoxyphenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H42N2O8
3-[3-cyclopentylpropanoyl-[2-(3-methoxyphenyl)ethyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[hept-6-enoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H42N2O8
3-[hept-6-enoyl-[2-(3-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 5-[(3S)-3-[[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]amino]cyclopentyl]-1H-pyridin-2-one —— C20H24N2O2
5-[(3S)-3-[[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]amino]cyclopentyl]-1H-pyridin-2-one
—— 3-[dodecanoyl(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C35H53N3O8
3-[dodecanoyl(2-morpholin-4-ylethyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cycloheptyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H38N2O5
3-[cycloheptyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (+/-) 2,2-Dimethyl-2,3-dihydro-benzofuran-7-carboxylic acid (4-oxo-2-pyridin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl)-amide 1036716-48-9 C23H22N4O3
(+/-) 2,2-Dimethyl-2,3-dihydro-benzofuran-7-carboxylic acid (4-oxo-2-pyridin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl)-amide
—— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H35N3O8
8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-morpholin-4-ylethyl(propanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[1-adamantylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C35H48N2O7
3-[1-adamantylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-(6-chloropyridin-3-yl)-N'-[[1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]piperidin-4-yl]methyl]-2-imidazol-1-ylbutanediamide —— C29H35ClN6O3
3-(6-chloropyridin-3-yl)-N'-[[1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]piperidin-4-yl]methyl]-2-imidazol-1-ylbutanediamide
—— 3-[dodecanoyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C37H51FN2O7
3-[dodecanoyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopropylmethyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H32N2O7
3-[cyclopropylmethyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[butanoyl-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H31FN2O7
3-[butanoyl-[(2-fluorophenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(3-methylbutyl)acetamide 762255-18-5 C17H25NO3
2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-(3-methylbutyl)acetamide
—— 2,3-dihydro-benzofuran-4-carboxylic acid [(R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-thiazolidin-4-ylmethyl]-amide 1061589-58-9 C25H25N3O3S2
2,3-dihydro-benzofuran-4-carboxylic acid [(R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-thiazolidin-4-ylmethyl]-amide
—— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O8
8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(2-oxobutanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— methyl 2-[(2S,3R)-5-hydroxy-2-methoxy-6-methyl-2,3-dihydro-1-benzofuran-3-yl]benzoate —— C18H18O5
methyl 2-[(2S,3R)-5-hydroxy-2-methoxy-6-methyl-2,3-dihydro-1-benzofuran-3-yl]benzoate
—— 3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H29ClN2O5
3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— [1-[3-(Diethylazaniumyl)propyl]-4,5-dioxo-2-thiophen-2-ylpyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate —— C25H30N2O4S
[1-[3-(Diethylazaniumyl)propyl]-4,5-dioxo-2-thiophen-2-ylpyrrolidin-3-ylidene]-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate
—— 1-[3-(Diethylamino)propyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione —— C25H30N2O4S
1-[3-(Diethylamino)propyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione
—— 3-[cyclobutanecarbonyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H28N2O6
3-[cyclobutanecarbonyl(furan-3-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cycloheptyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H38N2O7
3-[cycloheptyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cycloheptyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H40N2O8
3-[cycloheptyl(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclobutanecarbonyl(cycloheptyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H40N2O7
3-[cyclobutanecarbonyl(cycloheptyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cycloheptyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H42N2O7
3-[cycloheptyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[benzyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H34N2O8
3-[benzyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 1-(2,3-dihydro-1-benzofuran-5-yl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone —— C12H11N3O2
1-(2,3-dihydro-1-benzofuran-5-yl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone
—— 4-methyl-6-methylidene-N-[1-(3-methyl-2-methylidene-3H-1-benzofuran-6-yl)hexan-2-yl]-5-propylcyclohexa-2,4-dien-1-imine —— C27H35NO
4-methyl-6-methylidene-N-[1-(3-methyl-2-methylidene-3H-1-benzofuran-6-yl)hexan-2-yl]-5-propylcyclohexa-2,4-dien-1-imine
—— (9aS)-8-acetyl-N-benzyl-1-hydroxy-9a-methyl-7,9-dioxo-3-phenylmethoxydibenzofuran-4-carboxamide —— C30H25NO7
(9aS)-8-acetyl-N-benzyl-1-hydroxy-9a-methyl-7,9-dioxo-3-phenylmethoxydibenzofuran-4-carboxamide
—— 3-[cyclopropylmethyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H50N2O7
3-[cyclopropylmethyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[(3,4-dichlorophenyl)methyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H32Cl2N2O5
3-[(3,4-dichlorophenyl)methyl-hept-6-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[3-ethoxypropyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O9
3-[3-ethoxypropyl-(2-methoxyacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H40N2O5
3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (8-hydroxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-yl) hydrogen carbonate —— C18H16O5
(8-hydroxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-yl) hydrogen carbonate
—— 1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-3-[(2-methoxyphenyl)methylamino]propan-2-ol —— C21H27NO4
1-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-3-[(2-methoxyphenyl)methylamino]propan-2-ol
—— 3-[1-adamantylmethyl(cyclobutanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H44N2O7
3-[1-adamantylmethyl(cyclobutanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclobutanecarbonyl(cyclohexylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O5
3-[cyclobutanecarbonyl(cyclohexylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 4-(Cyclopropylmethyl)-10,14-dimethoxy-15-(phenylmethoxymethyl)-12-oxa-4-azapentacyclo[9.7.1.01,13.05,17.07,19]nonadeca-7(19),8,10-triene —— C31H39NO4
4-(Cyclopropylmethyl)-10,14-dimethoxy-15-(phenylmethoxymethyl)-12-oxa-4-azapentacyclo[9.7.1.01,13.05,17.07,19]nonadeca-7(19),8,10-triene
—— methyl N-[[7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate —— C18H19NO3
methyl N-[[7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate
—— C-[7-(2,5-difluoro-phenyl)-2,3-dihydro-benzofuran-2-yl]-methylamine —— C15H13F2NO
C-[7-(2,5-difluoro-phenyl)-2,3-dihydro-benzofuran-2-yl]-methylamine
—— 4b,9b-Bis(2,3,4,5,6-pentamethylphenyl)-[1]benzofuro[3,2-b][1]benzofuran —— C36H38O2
4b,9b-Bis(2,3,4,5,6-pentamethylphenyl)-[1]benzofuro[3,2-b][1]benzofuran
—— tert-butyl N-tert-butyl-N-[3-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)propoxycarbonyl]carbamate —— C23H35NO5
tert-butyl N-tert-butyl-N-[3-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)propoxycarbonyl]carbamate
—— N-[2-(3-methyl-2,5,6,7-tetrahydrofuro[3,2-g]chromen-3-yl)phenyl]-N-(oxolan-2-ylmethyl)formamide —— C24H27NO4
N-[2-(3-methyl-2,5,6,7-tetrahydrofuro[3,2-g]chromen-3-yl)phenyl]-N-(oxolan-2-ylmethyl)formamide