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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
—— (2R)-N-cyclopropyl-2-methyl-2,3-dihydro-1-benzofuran-5-amine —— C12H15NO
(2R)-N-cyclopropyl-2-methyl-2,3-dihydro-1-benzofuran-5-amine
—— (3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexanoic acid —— C15H20O3
(3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexanoic acid
—— (3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexanoic acid —— C15H20O3
(3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexanoic acid
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(oxan-4-yl)ethanamine —— C15H21NO2
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(oxan-4-yl)ethanamine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(oxan-4-yl)ethanamine —— C15H21NO2
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(oxan-4-yl)ethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine —— C14H15NOS
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine —— C14H15NOS
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine
—— (3R)-3-cyclopentyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine —— C16H23NO
(3R)-3-cyclopentyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine
—— (3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-(furan-2-yl)propan-1-amine —— C15H17NO2
(3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-(furan-2-yl)propan-1-amine
—— (3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-(furan-2-yl)propan-1-amine —— C15H17NO2
(3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-3-(furan-2-yl)propan-1-amine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-2-ylethanamine —— C15H16N2O
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-2-ylethanamine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-4-ylethanamine —— C15H16N2O
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-4-ylethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-4-ylethanamine —— C15H16N2O
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-4-ylethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-phenylethanamine —— C16H17NO
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-phenylethanamine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-phenylethanamine —— C16H17NO
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-phenylethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-3-ylethanamine —— C15H16N2O
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-3-ylethanamine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-3-ylethanamine —— C15H16N2O
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-3-ylethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-2-ylethanamine —— C15H16N2O
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-pyridin-2-ylethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-dimethylbutane-1,4-diamine —— C14H22N2O
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-dimethylbutane-1,4-diamine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-dimethylbutane-1,4-diamine —— C14H22N2O
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-dimethylbutane-1,4-diamine
—— (3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexan-1-amine —— C15H23NO
(3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexan-1-amine
—— (3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexan-1-amine —— C15H23NO
(3S)-3-(2,3-dihydro-1-benzofuran-5-yl)-5-methylhexan-1-amine
—— (3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-4,4-dimethylpentan-1-amine —— C15H23NO
(3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-4,4-dimethylpentan-1-amine
—— (3S)-3-cyclobutyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine —— C15H21NO
(3S)-3-cyclobutyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine
—— (3R)-3-cyclobutyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine —— C15H21NO
(3R)-3-cyclobutyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(furan-2-yl)ethanamine —— C14H15NO2
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(furan-2-yl)ethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(furan-2-yl)ethanamine —— C14H15NO2
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(furan-2-yl)ethanamine
—— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutan-1-amine —— C14H21NO
(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutan-1-amine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutan-1-amine —— C14H21NO
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutan-1-amine
—— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-4-methylpentan-1-amine —— C14H21NO
(2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-4-methylpentan-1-amine
—— (2R)-2-cyclobutyl-2-(2,3-dihydro-1-benzofuran-5-yl)ethanamine —— C14H19NO
(2R)-2-cyclobutyl-2-(2,3-dihydro-1-benzofuran-5-yl)ethanamine
—— (2S)-2-cyclobutyl-2-(2,3-dihydro-1-benzofuran-5-yl)ethanamine —— C14H19NO
(2S)-2-cyclobutyl-2-(2,3-dihydro-1-benzofuran-5-yl)ethanamine
—— (3S)-3-cyclopropyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine —— C14H19NO
(3S)-3-cyclopropyl-3-(2,3-dihydro-1-benzofuran-5-yl)propan-1-amine
—— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-nitropyridin-3-yl)oxyacetamide —— C19H21N3O6
N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(2-nitropyridin-3-yl)oxyacetamide
—— 2-methyl-2,3-dihydrobenzofuran-4-carbaldehyd —— C10H10O2
2-methyl-2,3-dihydrobenzofuran-4-carbaldehyd
—— (2R)-2-methyl-2,3-dihydro-1-benzofuran-6-carbaldehyde —— C10H10O2
(2R)-2-methyl-2,3-dihydro-1-benzofuran-6-carbaldehyde
—— 2-methyl-2,3-dihydrobenzofuran-4-carbaldehyd —— C10H10O2
2-methyl-2,3-dihydrobenzofuran-4-carbaldehyd
—— (S)-2-Methyl-2,3-dihydrobenzofuran-6-carbaldehyde —— C10H10O2
(S)-2-Methyl-2,3-dihydrobenzofuran-6-carbaldehyde
—— (3S)-3-(2,3-dihydro-1-benzofuran-5-yl)pentan-1-amine —— C13H19NO
(3S)-3-(2,3-dihydro-1-benzofuran-5-yl)pentan-1-amine
—— (3R)-3-(2,3-dihydro-1-benzofuran-5-yl)pentan-1-amine —— C13H19NO
(3R)-3-(2,3-dihydro-1-benzofuran-5-yl)pentan-1-amine
—— (2S)-2-cyclopropyl-2-(2,3-dihydro-1-benzofuran-5-yl)ethanamine —— C13H17NO
(2S)-2-cyclopropyl-2-(2,3-dihydro-1-benzofuran-5-yl)ethanamine
—— 2-[5-(2,3-dihydro-1-benzofuran-5-yl)-2-methyl-1-propan-2-ylpyrrol-3-yl]acetic acid —— C18H21NO3
2-[5-(2,3-dihydro-1-benzofuran-5-yl)-2-methyl-1-propan-2-ylpyrrol-3-yl]acetic acid
—— 3-[4-(2,3-dihydro-1-benzofuran-5-yl)-2,6-dimethylpyrimidin-5-yl]propanoic acid —— C17H18N2O3
3-[4-(2,3-dihydro-1-benzofuran-5-yl)-2,6-dimethylpyrimidin-5-yl]propanoic acid
—— 2-[1-cyclopropyl-5-(2,3-dihydro-1-benzofuran-5-yl)-2-methylpyrrol-3-yl]acetic acid —— C18H19NO3
2-[1-cyclopropyl-5-(2,3-dihydro-1-benzofuran-5-yl)-2-methylpyrrol-3-yl]acetic acid
—— 2-(3-cyano-5-nitro-2-oxopyridin-1-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H20N4O6
2-(3-cyano-5-nitro-2-oxopyridin-1-yl)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
—— 2-(3-cyano-5-nitro-2-oxopyridin-1-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide —— C20H20N4O6
2-(3-cyano-5-nitro-2-oxopyridin-1-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]acetamide
—— (1R)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-N,N-dimethylethane-1,2-diamine —— C15H19N3OS
(1R)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazol-2-yl]-N,N-dimethylethane-1,2-diamine
—— 3-[(5R)-5-(2,3-dihydro-1-benzofuran-5-yl)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]propanoic acid —— C15H17NO5
3-[(5R)-5-(2,3-dihydro-1-benzofuran-5-yl)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]propanoic acid
—— 3-[(5S)-5-(2,3-dihydro-1-benzofuran-5-yl)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]propanoic acid —— C15H17NO5
3-[(5S)-5-(2,3-dihydro-1-benzofuran-5-yl)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]propanoic acid
—— 4-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)-1,3-thiazole-5-carboxylic acid —— C14H14N2O3S
4-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)-1,3-thiazole-5-carboxylic acid