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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
—— (2Z)-(4,6-dimethyl-1-benzofuran-3(2H)-ylidene)ethanoate —— C12H11O3-
(2Z)-(4,6-dimethyl-1-benzofuran-3(2H)-ylidene)ethanoate
—— (1R,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methyl-1,2-oxazol-5-yl)methyl]cyclopentan-1-amine —— C22H30N2O3
(1R,2S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methyl-1,2-oxazol-5-yl)methyl]cyclopentan-1-amine
—— N'-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-3-ylmethyl)ethane-1,2-diamine —— C22H31N3O2
N'-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-3-ylmethyl)ethane-1,2-diamine
—— (2S)-N-(3-methoxypropyl)-2-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C24H29NO4
(2S)-N-(3-methoxypropyl)-2-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
—— (3R,4R)-N,N-dimethyl-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-4-(2-piperidin-1-ylpyrimidin-4-yl)pyrrolidine-3-carboxamide —— C26H35N5O2
(3R,4R)-N,N-dimethyl-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-4-(2-piperidin-1-ylpyrimidin-4-yl)pyrrolidine-3-carboxamide
—— (2R)-N-(3-methoxypropyl)-2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C24H29NO4
(2R)-N-(3-methoxypropyl)-2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
—— N-[(2-methoxyphenyl)methyl]-2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-(pyridin-3-ylmethyl)acetamide —— C25H26N2O3
N-[(2-methoxyphenyl)methyl]-2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-(pyridin-3-ylmethyl)acetamide
—— 2-cyclopentyl-N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide —— C28H37N3O2
2-cyclopentyl-N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide
—— N-(3-fluorophenyl)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7-dihydro-4H-[1,2]oxazolo[4,5-c]pyridin-3-amine —— C22H22FN3O2
N-(3-fluorophenyl)-5-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7-dihydro-4H-[1,2]oxazolo[4,5-c]pyridin-3-amine
—— (4aR,9bR)-8,9b-dimethyl-2-[(4-methylpiperazin-1-yl)methyl]-4,4a-dihydrodibenzofuran-3-one —— C20H26N2O2
(4aR,9bR)-8,9b-dimethyl-2-[(4-methylpiperazin-1-yl)methyl]-4,4a-dihydrodibenzofuran-3-one
—— 2-methyl-7-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepin-4-one —— C19H23N3O2
2-methyl-7-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepin-4-one
—— 2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1-[4-[(2-methyl-1,3-thiazol-4-yl)methyl]piperazin-1-yl]ethanone —— C20H25N3O2S
2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1-[4-[(2-methyl-1,3-thiazol-4-yl)methyl]piperazin-1-yl]ethanone
—— (1R)-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine —— C20H22N2OS2
(1R)-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine
—— N-[(2S)-1-methoxypropan-2-yl]-2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(3-methylphenyl)methyl]acetamide —— C23H29NO3
N-[(2S)-1-methoxypropan-2-yl]-2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(3-methylphenyl)methyl]acetamide
—— N-[(2S)-1-methoxypropan-2-yl]-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(3-methylphenyl)methyl]acetamide —— C23H29NO3
N-[(2S)-1-methoxypropan-2-yl]-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(3-methylphenyl)methyl]acetamide
—— 2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(R)-(4-methylphenyl)-pyridin-4-ylmethyl]acetamide —— C24H24N2O2
2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(R)-(4-methylphenyl)-pyridin-4-ylmethyl]acetamide
—— 4-[(2Z)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholine —— C20H18ClFN2O5
4-[(2Z)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholine
—— N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-4-oxo-4-thiophen-2-ylbutanamide —— C19H21NO4S
N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-4-oxo-4-thiophen-2-ylbutanamide
—— (1E)-2-methyl-1-(3-morpholin-4-yl-5-nitro-3H-1-benzofuran-2-ylidene)propan-2-ol —— C16H20N2O5
(1E)-2-methyl-1-(3-morpholin-4-yl-5-nitro-3H-1-benzofuran-2-ylidene)propan-2-ol
—— (2S)-5-chloro-N-[2-[4-(difluoromethoxy)phenyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H16ClF2NO3
(2S)-5-chloro-N-[2-[4-(difluoromethoxy)phenyl]ethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-(2-phenoxyethyl)piperazin-1-yl]methanone —— C21H23ClN2O3
[(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-(2-phenoxyethyl)piperazin-1-yl]methanone
—— (2S)-5-chloro-N'-[2-(2-cyanophenoxy)acetyl]-2,3-dihydro-1-benzofuran-2-carbohydrazide —— C18H14ClN3O4
(2S)-5-chloro-N'-[2-(2-cyanophenoxy)acetyl]-2,3-dihydro-1-benzofuran-2-carbohydrazide
—— (2S)-5-chloro-N-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]methyl]-N-cyclopropyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H17Cl2N3O3
(2S)-5-chloro-N-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]methyl]-N-cyclopropyl-2,3-dihydro-1-benzofuran-2-carboxamide
—— 4-benzyl-3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1H-1,2,4-triazol-5-one —— C21H23N3O3S
4-benzyl-3-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1H-1,2,4-triazol-5-one
—— (2R)-2-[(2R)-1,2-dihydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-carbaldehyde —— C12H14O4
(2R)-2-[(2R)-1,2-dihydroxypropan-2-yl]-2,3-dihydro-1-benzofuran-5-carbaldehyde
—— ethyl (2E)-2-[(3R)-3-hydroxy-3-methyl-1-benzofuran-2-ylidene]acetate —— C13H14O4
ethyl (2E)-2-[(3R)-3-hydroxy-3-methyl-1-benzofuran-2-ylidene]acetate
—— [(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone —— C23H24ClNO5
[(2R)-5-chloro-2,3-dihydro-1-benzofuran-2-yl]-[4-(2,4,6-trimethoxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]methanone
—— (E)-{1-[3-(diethylammonio)propyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene}(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate —— C26H32N2O5
(E)-{1-[3-(diethylammonio)propyl]-2-(5-methylfuran-2-yl)-4,5-dioxopyrrolidin-3-ylidene}(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanolate
—— (2S)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-2-(4-methoxyphenoxy)propanamide —— C21H20N2O4S
(2S)-N-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-2-(4-methoxyphenoxy)propanamide
—— 1-[3-(diethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methylfuran-2-yl)-1,5-dihydro-2H-pyrrol-2-one —— C26H32N2O5
1-[3-(diethylamino)propyl]-3-hydroxy-4-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]-5-(5-methylfuran-2-yl)-1,5-dihydro-2H-pyrrol-2-one
—— (2R)-2-(3-bromophenoxy)-N'-[2-(2,3-dihydro-1-benzofuran-5-yl)acetyl]propanehydrazide —— C19H19BrN2O4
(2R)-2-(3-bromophenoxy)-N'-[2-(2,3-dihydro-1-benzofuran-5-yl)acetyl]propanehydrazide
—— (4E)-1-[2-(dimethylamino)ethyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione —— C23H26N2O5
(4E)-1-[2-(dimethylamino)ethyl]-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-(5-methylfuran-2-yl)pyrrolidine-2,3-dione
—— (4E)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-ylpyrrolidine-2,3-dione —— C24H20N2O5
(4E)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-ylpyrrolidine-2,3-dione
—— (4E)-5-(furan-2-yl)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione —— C23H19NO6
(4E)-5-(furan-2-yl)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione
—— (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione —— C24H20N2O5
(4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione
—— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione —— C25H21N3O4
(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-pyridin-4-yl-1-(pyridin-3-ylmethyl)pyrrolidine-2,3-dione
—— prop-2-enyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C27H23N3O6S
prop-2-enyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— prop-2-enyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C26H22N2O6S2
prop-2-enyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— prop-2-enyl 2-[(3E)-2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C26H22N2O7S
prop-2-enyl 2-[(3E)-2-(furan-2-yl)-3-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4,5-dioxopyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— ethyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C25H22N2O6S2
ethyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— methyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C25H21N3O6S
methyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-pyridin-4-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— methyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate —— C24H20N2O6S2
methyl 2-[(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2,3-dioxo-5-thiophen-2-ylpyrrolidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
—— (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)pyrrolidine-2,3-dione —— C25H28N2O6
(4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-morpholin-4-ylpropyl)pyrrolidine-2,3-dione
—— 3-hydroxy-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-1-[3-(morpholin-4-yl)propyl]-5-(thiophen-2-yl)-2,5-dihydro-1H-pyrrol-2-one —— C25H28N2O5S
3-hydroxy-4-(2-methyl-2,3-dihydro-1-benzofuran-5-carbonyl)-1-[3-(morpholin-4-yl)propyl]-5-(thiophen-2-yl)-2,5-dihydro-1H-pyrrol-2-one
—— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione —— C23H24N2O5
(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)-5-pyridin-4-ylpyrrolidine-2,3-dione
—— (4E)-1-[2-(dimethylamino)ethyl]-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione —— C22H24N2O5
(4E)-1-[2-(dimethylamino)ethyl]-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]pyrrolidine-2,3-dione
—— (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)pyrrolidine-2,3-dione —— C22H23NO6
(4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(3-methoxypropyl)pyrrolidine-2,3-dione
—— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione —— C21H21NO5S
(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-thiophen-2-ylpyrrolidine-2,3-dione
—— (4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-pyridin-4-ylpyrrolidine-2,3-dione —— C22H22N2O5
(4E)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)-5-pyridin-4-ylpyrrolidine-2,3-dione
—— (4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)pyrrolidine-2,3-dione —— C21H21NO6
(4E)-5-(furan-2-yl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-1-(2-methoxyethyl)pyrrolidine-2,3-dione