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 |
|
—— | (E)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(5-nitrofuran-2-yl)prop-2-enamide | —— | C19H20N2O6 |
|
—— | 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 |
|
—— | (3S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1,1-dioxothiolane-3-carboxamide | —— | C17H23NO5S |
|
—— | (2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide | —— | C21H23NO4 |
|
—— | (E)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-phenylsulfanylprop-2-enamide | —— | C21H23NO3S |
|
—— | (2R)-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 | —— | C20H21NO3 |
|
—— | (2S)-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 | —— | C18H16N2O2S2 |
|
—— | [(2R)-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 | —— | C19H22N4O3 |
|
—— | [4-(cyclopropylamino)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]-[(2S)-2,3-dihydro-1-benzofuran-2-yl]methanone | —— | C20H22N4O2 |
|
—— | 1-[(2R)-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 | —— | C16H16N4O |
|
—— | 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-[[(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-[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-[[(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 |
|
—— | 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)-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)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[2-oxo-5-(trifluoromethyl)pyridin-1-yl]acetamide | —— | C20H21F3N2O4 |
|
—— | 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-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 | —— | C19H24N4O2 |
|
—— | 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-[(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 |
|
—— | (4R)-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 | —— | C19H23N3O2 |
|
—— | 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-[(2R)-2,3-dihydro-1-benzofuran-2-carbonyl]-4,6,7,8-tetrahydropyrazolo[1,5-a][1,4]diazepin-2-yl]propanoic acid | —— | C19H21N3O4 |
|
—— | 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 |
|
—— | 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-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]imidazol-2-yl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine | —— | C19H21N5O |
|
—— | N-(3-methoxypropyl)-1-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-amine | —— | C20H32N2O2 |
|
—— | 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 |
|
—— | N-(3-methoxypropyl)-1-methyl-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-amine | —— | C20H32N2O2 |
|
—— | 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 |
|
—— | (2S)-5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate | —— | C10H9O4- |
|
—— | 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-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]imidazol-2-yl]thiophen-3-yl]prop-2-yn-1-ol | —— | C19H16N2O2S |
|
—— | 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-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-(4-methyl-1,3-thiazol-5-yl)ethanamine | —— | C17H22N2OS |
|
—— | 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-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide | —— | C26H35N3O2 |
|
—— | 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-[[(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-[(S)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-(1,3-thiazol-2-yl)methyl]propanamide | —— | C24H33N3O2S |
|
—— | 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-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]propan-1-one | —— | C25H26N2O3S |
|