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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
—— (4S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-ethyl-4,5-dihydro-1,3-thiazol-2-amine —— C14H18N2OS
(4S)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-ethyl-4,5-dihydro-1,3-thiazol-2-amine
—— (3S)-1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-ethylpyrrolidin-3-amine —— C15H22N2O
(3S)-1-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-N-ethylpyrrolidin-3-amine
—— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1,5-diazocane —— C15H22N2O
1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1,5-diazocane
—— 2-amino-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]ethanesulfonamide —— C11H16N2O3S
2-amino-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]ethanesulfonamide
—— 2-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridine-2,5-diamine —— C14H15N3O
2-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridine-2,5-diamine
—— 3-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-fluorobenzene-1,3-diamine —— C15H15FN2O
3-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-fluorobenzene-1,3-diamine
—— (4R)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-ethyl-4,5-dihydro-1,3-thiazol-2-amine —— C14H18N2OS
(4R)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-ethyl-4,5-dihydro-1,3-thiazol-2-amine
—— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidin-4-one —— C14H17NO2
1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidin-4-one
—— 4-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-methyl-1H-1,2,4-triazole-5-thione —— C12H13N3OS
4-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-methyl-1H-1,2,4-triazole-5-thione
—— 5-amino-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1H-pyrazole-4-carboxamide —— C13H14N4O2
5-amino-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1H-pyrazole-4-carboxamide
—— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(2-methoxyacetyl)-(3-methylbutyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O8
8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[(2-methoxyacetyl)-(3-methylbutyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
—— 2-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridine-2,4-diamine —— C14H15N3O
2-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyridine-2,4-diamine
—— 4-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]benzene-1,4-diamine —— C15H16N2O
4-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]benzene-1,4-diamine
—— 1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidin-4-amine —— C14H20N2O
1-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidin-4-amine
—— (2S)-N-tert-butyl-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)acetamide —— C14H18ClNO2
(2S)-N-tert-butyl-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)acetamide
—— (2S)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylacetamide —— C14H18ClNO2
(2S)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylacetamide
—— (2R)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylacetamide —— C14H18ClNO2
(2R)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-N,N-diethylacetamide
—— (2R)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-1-morpholin-4-ylethanone —— C14H16ClNO3
(2R)-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)-1-morpholin-4-ylethanone
—— (2R)-N-tert-butyl-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)acetamide —— C14H18ClNO2
(2R)-N-tert-butyl-2-chloro-2-(2,3-dihydro-1-benzofuran-5-yl)acetamide
—— (R)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanol —— C14H18O3
(R)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanol
—— (2S)-5-[(R)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19ClO2
(2S)-5-[(R)-chloro-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
—— 5-[(R)-bromo-[(2R)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran —— C14H17BrO2
5-[(R)-bromo-[(2R)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran
—— 5-[(S)-bromo-[(2R)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran —— C14H17BrO2
5-[(S)-bromo-[(2R)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran
—— (2R)-5-[(S)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19BrO2
(2R)-5-[(S)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
—— (2R)-5-[(R)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran —— C15H19BrO2
(2R)-5-[(R)-bromo-[(2S)-oxan-2-yl]methyl]-2-methyl-2,3-dihydro-1-benzofuran
—— (R)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanol —— C14H18O3
(R)-2,3-dihydro-1-benzofuran-5-yl-[(2R)-oxan-2-yl]methanol
—— 5-[(R)-bromo-[(2S)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran —— C14H17BrO2
5-[(R)-bromo-[(2S)-oxan-2-yl]methyl]-2,3-dihydro-1-benzofuran
—— (S)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanamine —— C14H19NO2
(S)-2,3-dihydro-1-benzofuran-5-yl-[(2S)-oxan-2-yl]methanamine
—— [(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-[(2R)-oxan-2-yl]methanone —— C15H18O3
[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-[(2R)-oxan-2-yl]methanone
—— [(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-[(2R)-oxan-2-yl]methanone —— C15H18O3
[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-[(2R)-oxan-2-yl]methanone
—— [(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-[(2S)-oxan-2-yl]methanone —— C15H18O3
[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-[(2S)-oxan-2-yl]methanone
—— (1S)-1-(5-chlorothiophen-2-yl)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methylmethanamine —— C14H14ClNOS
(1S)-1-(5-chlorothiophen-2-yl)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methylmethanamine
—— (R)-cyclohepten-1-yl(2,3-dihydro-1-benzofuran-5-yl)methanamine —— C16H21NO
(R)-cyclohepten-1-yl(2,3-dihydro-1-benzofuran-5-yl)methanamine
—— N-[(2R)-2-cyanobutan-2-yl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C14H16N2O2
N-[(2R)-2-cyanobutan-2-yl]-2,3-dihydro-1-benzofuran-5-carboxamide
—— N-[(R)-(5-chlorothiophen-2-yl)-(2,3-dihydro-1-benzofuran-5-yl)methyl]ethanamine —— C15H16ClNOS
N-[(R)-(5-chlorothiophen-2-yl)-(2,3-dihydro-1-benzofuran-5-yl)methyl]ethanamine
—— 5-[(S)-chloro-(2,5-difluorophenyl)methyl]-2,3-dihydro-1-benzofuran —— C15H11ClF2O
5-[(S)-chloro-(2,5-difluorophenyl)methyl]-2,3-dihydro-1-benzofuran
—— N-[(2E)-2-amino-2-hydroxyiminoethyl]-N-methyl-2,3-dihydro-1-benzofuran-5-carboxamide —— C12H15N3O3
N-[(2E)-2-amino-2-hydroxyiminoethyl]-N-methyl-2,3-dihydro-1-benzofuran-5-carboxamide
—— (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine —— C14H15NOS
(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-thiophen-2-ylethanamine
—— 5-[(S)-bromo-(2,5-difluorophenyl)methyl]-2,3-dihydro-1-benzofuran —— C15H11BrF2O
5-[(S)-bromo-(2,5-difluorophenyl)methyl]-2,3-dihydro-1-benzofuran
—— (R)-cyclopropyl-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]methanamine —— C14H15N3O2
(R)-cyclopropyl-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]methanamine
—— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-1-(1-ethylimidazol-2-yl)-N-methylmethanamine —— C15H19N3O
(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-1-(1-ethylimidazol-2-yl)-N-methylmethanamine
—— 5-[(R)-chloro-(2,5-difluorophenyl)methyl]-2,3-dihydro-1-benzofuran —— C15H11ClF2O
5-[(R)-chloro-(2,5-difluorophenyl)methyl]-2,3-dihydro-1-benzofuran
—— N-ethyl-N-[(3R)-pyrrolidin-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C15H20N2O2
N-ethyl-N-[(3R)-pyrrolidin-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide
—— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-(1H-imidazol-2-yl)ethanamine —— C13H15N3O
(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-(1H-imidazol-2-yl)ethanamine
—— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-ethyl-2-thiophen-2-ylethanamine —— C16H19NOS
(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-ethyl-2-thiophen-2-ylethanamine
—— (S)-(2,5-dibromothiophen-3-yl)-(2,3-dihydro-1-benzofuran-5-yl)methanol —— C13H10Br2O2S
(S)-(2,5-dibromothiophen-3-yl)-(2,3-dihydro-1-benzofuran-5-yl)methanol
—— N-[(R)-cyclohexen-1-yl(2,3-dihydro-1-benzofuran-5-yl)methyl]ethanamine —— C17H23NO
N-[(R)-cyclohexen-1-yl(2,3-dihydro-1-benzofuran-5-yl)methyl]ethanamine
—— (1S)-1-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]ethanamine —— C12H13N3O2
(1S)-1-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]ethanamine
—— (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-(1H-imidazol-2-yl)ethanamine —— C13H15N3O
(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-2-(1H-imidazol-2-yl)ethanamine
—— (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-ethyl-2-thiophen-2-ylethanamine —— C16H19NOS
(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-ethyl-2-thiophen-2-ylethanamine