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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
—— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-methyl-4-oxo-1-phenylpyridazine-3-carboxamide —— C24H25N3O4
N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-6-methyl-4-oxo-1-phenylpyridazine-3-carboxamide
—— (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-nitrofuran-2-yl)prop-2-enamide —— C19H20N2O6
(E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-nitrofuran-2-yl)prop-2-enamide
—— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propanamide —— C24H27N3O4
N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propanamide
—— (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide —— C17H23NO5S
(3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide
—— (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C21H23NO4
(2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-phenylsulfanylprop-2-enamide —— C21H23NO3S
(E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-phenylsulfanylprop-2-enamide
—— (2R)-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H21NO3
(2R)-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (2S)-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H21NO3
(2S)-N-cyclopropyl-N-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (2S)-N-methyl-N-[(2-thiophen-2-yl-1,3-thiazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H16N2O2S2
(2S)-N-methyl-N-[(2-thiophen-2-yl-1,3-thiazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— (2R)-N-methyl-N-[(2-thiophen-2-yl-1,3-thiazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C18H16N2O2S2
(2R)-N-methyl-N-[(2-thiophen-2-yl-1,3-thiazol-4-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
—— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(2-hydroxyethylamino)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]methanone —— C19H22N4O3
[(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-(2-hydroxyethylamino)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]methanone
—— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[4-(2-hydroxyethylamino)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]methanone —— C19H22N4O3
[(2S)-2,3-dihydro-1-benzofuran-2-yl]-[4-(2-hydroxyethylamino)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]methanone
—— [4-(cyclopropylamino)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]-[(2S)-2,3-dihydro-1-benzofuran-2-yl]methanone —— C20H22N4O2
[4-(cyclopropylamino)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]-[(2S)-2,3-dihydro-1-benzofuran-2-yl]methanone
—— 1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-2-(5-methyl-1H-imidazol-4-yl)imidazole —— C16H16N4O
1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-2-(5-methyl-1H-imidazol-4-yl)imidazole
—— 1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-2-(5-methyl-1H-imidazol-4-yl)imidazole —— C16H16N4O
1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-2-(5-methyl-1H-imidazol-4-yl)imidazole
—— 2-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine —— C19H24N4O
2-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine
—— 2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine —— C19H24N4O
2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine
—— 2-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine —— C20H23N5O
2-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine
—— 2-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine —— C20H23N5O
2-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine
—— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-oxo-5-(trifluoromethyl)pyridin-1-yl]acetamide —— C20H21F3N2O4
N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-oxo-5-(trifluoromethyl)pyridin-1-yl]acetamide
—— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine —— C18H22N4O
N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine
—— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-oxo-5-(trifluoromethyl)pyridin-1-yl]acetamide —— C20H21F3N2O4
N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-oxo-5-(trifluoromethyl)pyridin-1-yl]acetamide
—— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine —— C18H22N4O
N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-amine
—— N-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-3-(5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl)propanamide —— C19H24N4O2
N-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-3-(5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl)propanamide
—— N-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-3-(5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl)propanamide —— C19H24N4O2
N-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-3-(5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-2-yl)propanamide
—— 2-[1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine —— C19H21N5O
2-[1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine
—— 2-[1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine —— C19H21N5O
2-[1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine
—— (4R)-4-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-1-ethylpyrrolidin-2-one —— C19H23N3O2
(4R)-4-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-1-ethylpyrrolidin-2-one
—— (4S)-4-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-1-ethylpyrrolidin-2-one —— C19H23N3O2
(4S)-4-[2-(2,2-dimethyl-3H-1-benzofuran-5-yl)imidazol-1-yl]-1-ethylpyrrolidin-2-one
—— 3-[5-[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]-4,6,7,8-tetrahydropyrazolo[1,5-a][1,4]diazepin-2-yl]propanoic acid —— C19H21N3O4
3-[5-[(2S)-2,3-dihydro-1-benzofuran-2-carbonyl]-4,6,7,8-tetrahydropyrazolo[1,5-a][1,4]diazepin-2-yl]propanoic acid
—— 3-[5-[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]-4,6,7,8-tetrahydropyrazolo[1,5-a][1,4]diazepin-2-yl]propanoic acid —— C19H21N3O4
3-[5-[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]-4,6,7,8-tetrahydropyrazolo[1,5-a][1,4]diazepin-2-yl]propanoic acid
—— 1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-methyl-N-[(5-methylsulfonyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-2-yl)methyl]methanamine —— C18H24N4O3S
1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-methyl-N-[(5-methylsulfonyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-2-yl)methyl]methanamine
—— 2-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine —— C19H21N5O
2-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine
—— 2-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine —— C19H21N5O
2-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine
—— N-(3-methoxypropyl)-1-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-amine —— C20H32N2O2
N-(3-methoxypropyl)-1-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-amine
—— 2-[1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine —— C18H19N5O
2-[1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine
—— N-(3-methoxypropyl)-1-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-amine —— C20H32N2O2
N-(3-methoxypropyl)-1-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-amine
—— 2-[1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine —— C18H19N5O
2-[1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine
—— (2S)-5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate —— C10H9O4-
(2S)-5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate
—— 3-[5-[1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]thiophen-3-yl]prop-2-yn-1-ol —— C19H16N2O2S
3-[5-[1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]thiophen-3-yl]prop-2-yn-1-ol
—— 3-[5-[1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]thiophen-3-yl]prop-2-yn-1-ol —— C19H16N2O2S
3-[5-[1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]thiophen-3-yl]prop-2-yn-1-ol
—— N-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-(4-methyl-1,3-thiazol-5-yl)ethanamine —— C17H22N2OS
N-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-(4-methyl-1,3-thiazol-5-yl)ethanamine
—— N-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-(4-methyl-1,3-thiazol-5-yl)ethanamine —— C17H22N2OS
N-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-(4-methyl-1,3-thiazol-5-yl)ethanamine
—— 2,2-dimethyl-N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide —— C26H35N3O2
2,2-dimethyl-N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide
—— 2,2-dimethyl-N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide —— C26H35N3O2
2,2-dimethyl-N-[(S)-[(3S)-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide
—— 2,2-dimethyl-N-[(R)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-(1,3-thiazol-2-yl)methyl]propanamide —— C24H33N3O2S
2,2-dimethyl-N-[(R)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-(1,3-thiazol-2-yl)methyl]propanamide
—— 2,2-dimethyl-N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-(1,3-thiazol-2-yl)methyl]propanamide —— C24H33N3O2S
2,2-dimethyl-N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-(1,3-thiazol-2-yl)methyl]propanamide
—— 2,2-dimethyl-N-[(S)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-(1,3-thiazol-2-yl)methyl]propanamide —— C24H33N3O2S
2,2-dimethyl-N-[(S)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-(1,3-thiazol-2-yl)methyl]propanamide
—— 1-[2-(3-methoxyphenyl)-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-5-yl]-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propan-1-one —— C25H26N2O3S
1-[2-(3-methoxyphenyl)-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-5-yl]-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propan-1-one
—— 1-[2-(3-methoxyphenyl)-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-5-yl]-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propan-1-one —— C25H26N2O3S
1-[2-(3-methoxyphenyl)-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-5-yl]-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propan-1-one