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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
—— (3S)-3-[[(2S)-2-(dimethylamino)propyl]amino]-2,3-dihydro-1-benzofuran-6-ol —— C13H20N2O2
(3S)-3-[[(2S)-2-(dimethylamino)propyl]amino]-2,3-dihydro-1-benzofuran-6-ol
—— (3R)-3-[[(2S)-2-(dimethylamino)propyl]amino]-2,3-dihydro-1-benzofuran-6-ol —— C13H20N2O2
(3R)-3-[[(2S)-2-(dimethylamino)propyl]amino]-2,3-dihydro-1-benzofuran-6-ol
—— (2S)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C16H26N2O
(2S)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine
—— (2R)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C15H24N2O
(2R)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine
—— (2R)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C16H26N2O
(2R)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine
—— (2R)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C15H24N2O
(2R)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine
—— (2S)-1-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-N,2-N-dimethylpropane-1,2-diamine —— C14H22N2O
(2S)-1-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-N,2-N-dimethylpropane-1,2-diamine
—— (2S)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C15H24N2O
(2S)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine
—— (2R)-1-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-N,2-N-dimethylpropane-1,2-diamine —— C14H22N2O
(2R)-1-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-N,2-N-dimethylpropane-1,2-diamine
—— (3R)-3-(1,4-diazepan-1-yl)-2,3-dihydro-1-benzofuran-6-ol —— C13H18N2O2
(3R)-3-(1,4-diazepan-1-yl)-2,3-dihydro-1-benzofuran-6-ol
—— (3S)-3-(1,4-diazepan-1-yl)-2,3-dihydro-1-benzofuran-6-ol —— C13H18N2O2
(3S)-3-(1,4-diazepan-1-yl)-2,3-dihydro-1-benzofuran-6-ol
—— (2S)-2-(azepan-1-yl)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile —— C16H20N2O
(2S)-2-(azepan-1-yl)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile
—— (3R)-3-(azepan-1-yl)-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C15H18N2O2
(3R)-3-(azepan-1-yl)-6-hydroxy-2H-1-benzofuran-3-carbonitrile
—— (3R)-3-[[(3S)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol —— C13H17NO4S
(3R)-3-[[(3S)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol
—— (3R)-3-[[(3R)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol —— C13H17NO4S
(3R)-3-[[(3R)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol
—— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H36N2O7
4-hydroxy-N-(2-hydroxyethyl)-3-[2-(2-methoxyphenyl)ethyl-(5-oxohexanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[cyclobutanecarbonyl(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O6
3-[cyclobutanecarbonyl(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— (3S)-3-[[(3S)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol —— C13H17NO4S
(3S)-3-[[(3S)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol
—— 3-[cyclobutanecarbonyl(oxolan-2-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O8
3-[cyclobutanecarbonyl(oxolan-2-ylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— [4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine —— C16H17NO
[4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine
—— [2-fluoro-4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine —— C16H16FNO
[2-fluoro-4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine
—— (1R)-1-[3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
(1R)-1-[3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
—— [4-fluoro-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine —— C16H16FNO
[4-fluoro-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine
—— [4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine —— C16H17NO
[4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine
—— (1R)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine —— C17H19NO
(1R)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine
—— [2-fluoro-4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine —— C16H16FNO
[2-fluoro-4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine
—— (1R)-1-[2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
(1R)-1-[2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
—— 2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H14O2
2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— (1R)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine —— C16H17NO
(1R)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine
—— (1R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine —— C16H17NO
(1R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine
—— (1S)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine —— C16H17NO
(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine
—— (1S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine —— C16H17NO
(1S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine
—— (1S)-1-[2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
(1S)-1-[2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
—— (1R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine —— C17H19NO
(1R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine
—— 2-fluoro-5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H13FO2
2-fluoro-5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— (1S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine —— C17H19NO
(1S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine
—— (1S)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine —— C17H19NO
(1S)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine
—— (1R)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine —— C16H17NO
(1R)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine
—— (1S)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine —— C17H19NO
(1S)-1-[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine
—— (1S)-1-[3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
(1S)-1-[3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
—— 4-fluoro-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H13FO2
4-fluoro-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— 2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H14O2
2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— 2-fluoro-4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H13FO2
2-fluoro-4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[oxolane-3-carbonyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O9
4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[oxolane-3-carbonyl(oxolan-2-ylmethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H14O2
3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— 4-fluoro-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H13FO2
4-fluoro-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— 4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H14O2
4-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
—— 4-fluoro-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]aniline —— C15H14FNO
4-fluoro-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]aniline
—— 2-methyl-5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]aniline —— C16H17NO
2-methyl-5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]aniline
—— 3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzoic acid —— C16H14O3
3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzoic acid