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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-[(3R)-1,1-dioxothiolan-3-yl]-N-ethyl-2,3-dihydro-1-benzofuran-7-carboxamide —— C15H19NO4S
N-[(3R)-1,1-dioxothiolan-3-yl]-N-ethyl-2,3-dihydro-1-benzofuran-7-carboxamide
—— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3-methylpyridin-2-yl)methyl]piperazin-1-yl]methanone —— C20H23N3O2
[(2R)-2,3-dihydro-1-benzofuran-2-yl]-[4-[(3-methylpyridin-2-yl)methyl]piperazin-1-yl]methanone
—— [(2R)-5-methyl-7-[6-(1-methylimidazol-2-yl)pyridazin-3-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H19N5O
[(2R)-5-methyl-7-[6-(1-methylimidazol-2-yl)pyridazin-3-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-5-methyl-7-[6-(1-methylimidazol-2-yl)pyridazin-3-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H19N5O
[(2S)-5-methyl-7-[6-(1-methylimidazol-2-yl)pyridazin-3-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(5,6-dimethylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H18N2O
[(2S)-7-(5,6-dimethylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(5,6-dimethylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H18N2O
[(2R)-7-(5,6-dimethylpyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(5-ethylpyrimidin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C15H16FN3O
[(2S)-7-(5-ethylpyrimidin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-chloro-5-(5-fluoropyrimidin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C13H11ClFN3O
[(2R)-7-chloro-5-(5-fluoropyrimidin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(5-ethylpyrimidin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C15H16FN3O
[(2R)-7-(5-ethylpyrimidin-2-yl)-4-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— 2-[(2S)-2-(aminomethyl)-5-chloro-2,3-dihydro-1-benzofuran-7-yl]-N,6-dimethylpyrimidin-4-amine —— C15H17ClN4O
2-[(2S)-2-(aminomethyl)-5-chloro-2,3-dihydro-1-benzofuran-7-yl]-N,6-dimethylpyrimidin-4-amine
—— 1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[[2-(furan-2-yl)-1,3-thiazol-4-yl]methyl]methanamine —— C17H16N2O2S
1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[[2-(furan-2-yl)-1,3-thiazol-4-yl]methyl]methanamine
—— 2-[(2R)-2-(aminomethyl)-5-chloro-2,3-dihydro-1-benzofuran-7-yl]-N,6-dimethylpyrimidin-4-amine —— C15H17ClN4O
2-[(2R)-2-(aminomethyl)-5-chloro-2,3-dihydro-1-benzofuran-7-yl]-N,6-dimethylpyrimidin-4-amine
—— 4-ethyl-2-methyl-5-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-1,2,4-triazol-3-one —— C20H28N4O2
4-ethyl-2-methyl-5-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-1,2,4-triazol-3-one
—— (3R)-1-[3-[2-(2,3-dihydro-1-benzofuran-5-yl)imidazol-1-yl]propyl]piperidin-3-ol —— C19H25N3O2
(3R)-1-[3-[2-(2,3-dihydro-1-benzofuran-5-yl)imidazol-1-yl]propyl]piperidin-3-ol
—— 4-ethyl-2-methyl-5-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-1,2,4-triazol-3-one —— C20H28N4O2
4-ethyl-2-methyl-5-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-1,2,4-triazol-3-one
—— 4-[(2R)-2-(aminomethyl)-5-fluoro-2,3-dihydro-1-benzofuran-7-yl]-6-methoxypyrimidin-2-amine —— C14H15FN4O2
4-[(2R)-2-(aminomethyl)-5-fluoro-2,3-dihydro-1-benzofuran-7-yl]-6-methoxypyrimidin-2-amine
—— 4-[(2S)-2-(aminomethyl)-5-fluoro-2,3-dihydro-1-benzofuran-7-yl]-6-methoxypyrimidin-2-amine —— C14H15FN4O2
4-[(2S)-2-(aminomethyl)-5-fluoro-2,3-dihydro-1-benzofuran-7-yl]-6-methoxypyrimidin-2-amine
—— 5-[(2S)-2-(aminomethyl)-5-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-benzyl-N,N-dimethyl-1,2,4-triazol-3-amine —— C21H25N5O
5-[(2S)-2-(aminomethyl)-5-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-benzyl-N,N-dimethyl-1,2,4-triazol-3-amine
—— [(2R)-5-methyl-7-pyrazin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H15N3O
[(2R)-5-methyl-7-pyrazin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-4-fluoro-7-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H20FNO4
[(2S)-4-fluoro-7-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— 5-[(2R)-2-(aminomethyl)-5-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-benzyl-N,N-dimethyl-1,2,4-triazol-3-amine —— C21H25N5O
5-[(2R)-2-(aminomethyl)-5-methyl-2,3-dihydro-1-benzofuran-7-yl]-2-benzyl-N,N-dimethyl-1,2,4-triazol-3-amine
—— [(2R)-7-(3-fluoro-4-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H16FNO2
[(2R)-7-(3-fluoro-4-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-5-methyl-7-pyrazin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H15N3O
[(2S)-5-methyl-7-pyrazin-2-yl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(5-chloropyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H13ClN2O
[(2R)-7-(5-chloropyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(5-chloropyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H13ClN2O
[(2S)-7-(5-chloropyridin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-[3-(aminomethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H18N2O
[(2S)-7-[3-(aminomethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-[3-(aminomethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H18N2O
[(2R)-7-[3-(aminomethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-5-(5-ethylpyrimidin-2-yl)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C15H16FN3O
[(2S)-5-(5-ethylpyrimidin-2-yl)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-4-fluoro-7-[5-(imidazol-1-ylmethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H17FN4O
[(2S)-4-fluoro-7-[5-(imidazol-1-ylmethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(5-fluoropyridin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C15H15FN2O
[(2R)-7-(5-fluoropyridin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-5-(5-ethylpyrimidin-2-yl)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C15H16FN3O
[(2R)-5-(5-ethylpyrimidin-2-yl)-7-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(5-fluoropyridin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C15H15FN2O
[(2S)-7-(5-fluoropyridin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-4-fluoro-7-[5-(imidazol-1-ylmethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H17FN4O
[(2R)-4-fluoro-7-[5-(imidazol-1-ylmethyl)pyridin-2-yl]-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(2-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H16ClNO
[(2S)-7-(2-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(2-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H16ClNO
[(2R)-7-(2-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(2,4-difluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H15F2NO
[(2S)-7-(2,4-difluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(5-fluoropyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H14FN3O
[(2S)-7-(5-fluoropyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(2,4-difluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H15F2NO
[(2R)-7-(2,4-difluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(5-fluoropyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H14FN3O
[(2R)-7-(5-fluoropyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [4-[(2S)-2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-3-(hydroxymethyl)phenyl]methanol —— C17H19NO3
[4-[(2S)-2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-3-(hydroxymethyl)phenyl]methanol
—— [4-[(2R)-2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-3-(hydroxymethyl)phenyl]methanol —— C17H19NO3
[4-[(2R)-2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-3-(hydroxymethyl)phenyl]methanol
—— [(2S)-7-(4-methylpyrimidin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H15N3O
[(2S)-7-(4-methylpyrimidin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-5-methyl-7-(2-methyl-5-propylpyrimidin-4-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C18H23N3O
[(2S)-5-methyl-7-(2-methyl-5-propylpyrimidin-4-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(4-methylpyrimidin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C14H15N3O
[(2R)-7-(4-methylpyrimidin-2-yl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-[5-(aminomethyl)pyridin-2-yl]-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H19N3O
[(2S)-7-[5-(aminomethyl)pyridin-2-yl]-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-[5-(aminomethyl)pyridin-2-yl]-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C16H19N3O
[(2R)-7-[5-(aminomethyl)pyridin-2-yl]-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2S)-7-(4-ethyl-5-methylpyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C17H21N3O
[(2S)-7-(4-ethyl-5-methylpyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— [(2R)-7-(4-ethyl-5-methylpyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine —— C17H21N3O
[(2R)-7-(4-ethyl-5-methylpyrimidin-2-yl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methanamine
—— N-[(2R)-3-(2,3-dichlorophenoxy)-2-hydroxypropyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C18H17Cl2NO4
N-[(2R)-3-(2,3-dichlorophenoxy)-2-hydroxypropyl]-2,3-dihydro-1-benzofuran-5-carboxamide
—— N-(1H-imidazol-2-ylmethyl)-N-methyl-1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine —— C15H19N3O
N-(1H-imidazol-2-ylmethyl)-N-methyl-1-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methanamine