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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-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1R,3S)-3-(trifluoromethyl)cyclohexyl]acetamide —— C19H24F3NO3
2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[(1R,3S)-3-(trifluoromethyl)cyclohexyl]acetamide
—— 3-[acetyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H34N2O7
3-[acetyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopentyl(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H38N2O7
3-[cyclopentyl(3-methylbutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[furan-3-ylmethyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H32N2O6
3-[furan-3-ylmethyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— Ethyl 2-(5-chloropyrimidin-2-yl)oxy-2-(2,3-dihydro-1-benzofuran-5-yl)acetate —— C16H15ClN2O4
Ethyl 2-(5-chloropyrimidin-2-yl)oxy-2-(2,3-dihydro-1-benzofuran-5-yl)acetate
—— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methylpropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H40N2O8
4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methylpropanoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methoxyethyl(pent-4-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H32N2O8
8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-methoxyethyl(pent-4-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[(3,4-dichlorophenyl)methyl-(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H30Cl2N2O8
3-[(3,4-dichlorophenyl)methyl-(oxolane-3-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(2-methylpropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H34N2O8
4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[2-methoxyethyl(2-methylpropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopropylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O8
3-[cyclopropylmethyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[(3,4-dichlorophenyl)methyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H28Cl2N2O5
3-[(3,4-dichlorophenyl)methyl-pent-2-enoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 8-formyl-3-[hexyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H40N2O7
8-formyl-3-[hexyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[(3,4-dichlorophenyl)methyl-pentanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H34Cl2N2O7
3-[(3,4-dichlorophenyl)methyl-pentanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[benzyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H28N2O5
3-[benzyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopentanecarbonyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H33FN2O5
3-[cyclopentanecarbonyl-[2-(3-fluorophenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopropanecarbonyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O5
3-[cyclopropanecarbonyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H42N2O7
3-[cyclohexylmethyl-(2-cyclopentylacetyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[dodecanoyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C37H52N2O7
3-[dodecanoyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (2S)-5-chloro-N-[3-[2-methoxyethyl(methyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H23ClN2O3
(2S)-5-chloro-N-[3-[2-methoxyethyl(methyl)amino]propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— 3-[cyclohexyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O6
3-[cyclohexyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclohexylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O5
3-[cyclohexylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cycloheptyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O6
3-[cycloheptyl(2-oxobutanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopentanecarbonyl(hexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H40N2O7
3-[cyclopentanecarbonyl(hexyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopropylmethyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H32N2O8
3-[cyclopropylmethyl(oxolane-2-carbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopropylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O7
3-[cyclopropylmethyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[hexyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H40N2O7
3-[hexyl(3-methylbut-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[3-cyclopentylpropanoyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O5
3-[3-cyclopentylpropanoyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (2R)-5-chloro-N-[3-(1,2,4-triazol-1-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H15ClN4O2
(2R)-5-chloro-N-[3-(1,2,4-triazol-1-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (2S)-5-chloro-N-[3-(1,2,4-triazol-1-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H15ClN4O2
(2S)-5-chloro-N-[3-(1,2,4-triazol-1-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— 3-[furan-3-ylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H34N2O8
3-[furan-3-ylmethyl(pentanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 8-formyl-3-[hept-6-enoyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H42N2O7
8-formyl-3-[hept-6-enoyl(hexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopentanecarbonyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C32H40N2O8
3-[cyclopentanecarbonyl-[2-(2-methoxyphenyl)ethyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (2R)-N-[(2R)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H24N2O3
(2R)-N-[(2R)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— 3-[2-(3-fluorophenyl)ethyl-pent-4-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H33FN2O7
3-[2-(3-fluorophenyl)ethyl-pent-4-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (2S)-N-[(2R)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H24N2O3
(2S)-N-[(2R)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (2R)-N-[(2S)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H24N2O3
(2R)-N-[(2S)-2-(dimethylamino)-2-(3-methoxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(pyridin-3-ylmethylsulfanyl)acetamide —— C20H24N2O3S
N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(pyridin-3-ylmethylsulfanyl)acetamide
—— 3-[(4-chlorophenyl)methyl-(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H35ClN2O7
3-[(4-chlorophenyl)methyl-(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 8-formyl-3-[furan-3-ylmethyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H38N2O8
8-formyl-3-[furan-3-ylmethyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)butanamide —— C19H25N3O4
N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)butanamide
—— (3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide —— C23H33N3O4
(3R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide
—— (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide —— C23H33N3O4
(3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide
—— (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide —— C23H33N3O4
(3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(pyrrolidine-1-carbonyl)piperidine-3-carboxamide
—— 5-[1-(4-Chlorophenyl)ethenyl]-2,3-dihydro-1-benzofuran —— C16H13ClO
5-[1-(4-Chlorophenyl)ethenyl]-2,3-dihydro-1-benzofuran
—— 3-[cyclopentyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O7
3-[cyclopentyl(pent-2-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[butanoyl(2,2,2-trifluoroethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C21H25F3N2O5
3-[butanoyl(2,2,2-trifluoroethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[(3,4-Difluorophenyl)methyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazolidin-4-one —— C18H15F2NO2S
3-[(3,4-Difluorophenyl)methyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazolidin-4-one
—— 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-(thiophen-2-ylmethyl)-1,3-thiazolidin-4-one —— C16H15NO2S2
2-(2,3-Dihydro-1-benzofuran-5-yl)-3-(thiophen-2-ylmethyl)-1,3-thiazolidin-4-one
—— 3-[dodecanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H46N2O6
3-[dodecanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclopentanecarbonyl(cyclopentyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O5
3-[cyclopentanecarbonyl(cyclopentyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide