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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)-5-tert-butyl-N-cyclopropyl-2,3-dihydro-1-benzofuran-3-amine —— C15H21NO
(3S)-5-tert-butyl-N-cyclopropyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5-propoxy-2,3-dihydro-1-benzofuran-3-amine —— C11H15NO2
(3S)-5-propoxy-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-7-tert-butyl-N,5-diethyl-2,3-dihydro-1-benzofuran-3-amine —— C16H25NO
(3R)-7-tert-butyl-N,5-diethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5,7-dichloro-N-ethyl-2,3-dihydro-1-benzofuran-3-amine —— C10H11Cl2NO
(3S)-5,7-dichloro-N-ethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-6,7-dimethyl-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine —— C13H19NO
(3R)-6,7-dimethyl-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-5-(2-methylbutan-2-yl)-N-propyl-2,3-dihydro-1-benzofuran-3-amine —— C16H25NO
(3R)-5-(2-methylbutan-2-yl)-N-propyl-2,3-dihydro-1-benzofuran-3-amine
—— (6R)-2,2-dimethyl-N-propyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine —— C15H21NO2
(6R)-2,2-dimethyl-N-propyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine
—— (3R)-5-Bromo-7-fluoro-2,3-dihydro-1-benzofuran-3-amine —— C8H7BrFNO
(3R)-5-Bromo-7-fluoro-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-5-bromo-7-fluoro-N-methyl-2,3-dihydro-1-benzofuran-3-amine —— C9H9BrFNO
(3R)-5-bromo-7-fluoro-N-methyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5-Bromo-7-fluoro-2,3-dihydro-1-benzofuran-3-amine —— C8H7BrFNO
(3S)-5-Bromo-7-fluoro-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-5-Ethoxy-2,3-dihydro-3-benzofuranamine 1228547-94-1 C10H13NO2
(3R)-5-Ethoxy-2,3-dihydro-3-benzofuranamine
—— (3S)-5-Bromo-7-chloro-2,3-dihydro-1-benzofuran-3-amine —— C8H7BrClNO
(3S)-5-Bromo-7-chloro-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5-ethoxy-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine —— C13H19NO2
(3S)-5-ethoxy-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5-ethoxy-N-methyl-2,3-dihydro-1-benzofuran-3-amine —— C11H15NO2
(3S)-5-ethoxy-N-methyl-2,3-dihydro-1-benzofuran-3-amine
—— (6R)-N-ethyl-2,2-dimethyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine —— C14H19NO2
(6R)-N-ethyl-2,2-dimethyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine
—— (3S)-7-tert-butyl-4-methyl-N-propyl-2,3-dihydro-1-benzofuran-3-amine —— C16H25NO
(3S)-7-tert-butyl-4-methyl-N-propyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-3-amine —— C10H13NO
(3S)-5,6-dimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-N-ethyl-5-(2-methylbutan-2-yl)-2,3-dihydro-1-benzofuran-3-amine —— C15H23NO
(3R)-N-ethyl-5-(2-methylbutan-2-yl)-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-N,4,6-trimethyl-2,3-dihydro-1-benzofuran-3-amine —— C11H15NO
(3R)-N,4,6-trimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-5-(2-methylbutan-2-yl)-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine —— C16H25NO
(3R)-5-(2-methylbutan-2-yl)-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-7-bromo-N,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine —— C10H12BrNO
(3R)-7-bromo-N,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-4,7-Dimethyl-2,3-dihydro-1-benzofuran-3-amine —— C10H13NO
(3R)-4,7-Dimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-5,7-difluoro-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine —— C11H13F2NO
(3R)-5,7-difluoro-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5-chloro-N-ethyl-7-methyl-2,3-dihydro-1-benzofuran-3-amine —— C11H14ClNO
(3S)-5-chloro-N-ethyl-7-methyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-amine —— C11H15NO
(3S)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (6R)-N-cyclopropyl-2,2-dimethyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine —— C15H19NO2
(6R)-N-cyclopropyl-2,2-dimethyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine
—— (3S)-7-bromo-N,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine —— C10H12BrNO
(3S)-7-bromo-N,5-dimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-N,5,6-trimethyl-2,3-dihydro-1-benzofuran-3-amine —— C11H15NO
(3R)-N,5,6-trimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-N-ethyl-4,7-dimethyl-2,3-dihydro-1-benzofuran-3-amine —— C12H17NO
(3S)-N-ethyl-4,7-dimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (6S)-2,2-dimethyl-N-propan-2-yl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine —— C15H21NO2
(6S)-2,2-dimethyl-N-propan-2-yl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine
—— (3S)-N-ethyl-5,6-dimethyl-2,3-dihydro-1-benzofuran-3-amine —— C12H17NO
(3S)-N-ethyl-5,6-dimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5,7-difluoro-N-propyl-2,3-dihydro-1-benzofuran-3-amine —— C11H13F2NO
(3S)-5,7-difluoro-N-propyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-7-tert-butyl-N-cyclopropyl-4-methyl-2,3-dihydro-1-benzofuran-3-amine —— C16H23NO
(3R)-7-tert-butyl-N-cyclopropyl-4-methyl-2,3-dihydro-1-benzofuran-3-amine
—— 2-[[5-[(2-chlorophenoxy)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide —— C22H23ClN4O4S
2-[[5-[(2-chlorophenoxy)methyl]-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]-N-[(3S)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetamide
—— (3S)-N,4,7-trimethyl-2,3-dihydro-1-benzofuran-3-amine —— C11H15NO
(3S)-N,4,7-trimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5,6-dimethyl-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine —— C13H19NO
(3S)-5,6-dimethyl-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5,7-difluoro-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine —— C11H13F2NO
(3S)-5,7-difluoro-N-propan-2-yl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-N-ethyl-5,7-difluoro-2,3-dihydro-1-benzofuran-3-amine —— C10H11F2NO
(3S)-N-ethyl-5,7-difluoro-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-7-tert-butyl-N-ethyl-4-methyl-2,3-dihydro-1-benzofuran-3-amine —— C15H23NO
(3S)-7-tert-butyl-N-ethyl-4-methyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-5,7-difluoro-N-methyl-2,3-dihydro-1-benzofuran-3-amine —— C9H9F2NO
(3R)-5,7-difluoro-N-methyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-5-ethoxy-2,3-dihydro-1-benzofuran-3-amine —— C10H13NO2
(3S)-5-ethoxy-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-4,7-Dimethyl-2,3-dihydro-1-benzofuran-3-amine —— C10H13NO
(3S)-4,7-Dimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-amine —— C11H15NO
(3R)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-amine
—— (6S)-2,2-dimethyl-N-propyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine —— C15H21NO2
(6S)-2,2-dimethyl-N-propyl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine
—— (3R)-7-tert-butyl-N-cyclopropyl-5-methyl-2,3-dihydro-1-benzofuran-3-amine —— C16H23NO
(3R)-7-tert-butyl-N-cyclopropyl-5-methyl-2,3-dihydro-1-benzofuran-3-amine
—— (3S)-N-cyclopropyl-5-(2-methylbutan-2-yl)-2,3-dihydro-1-benzofuran-3-amine —— C16H23NO
(3S)-N-cyclopropyl-5-(2-methylbutan-2-yl)-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-N-cyclopropyl-5-(2-methylbutan-2-yl)-2,3-dihydro-1-benzofuran-3-amine —— C16H23NO
(3R)-N-cyclopropyl-5-(2-methylbutan-2-yl)-2,3-dihydro-1-benzofuran-3-amine
—— (3R)-N-ethyl-5,7-difluoro-2,3-dihydro-1-benzofuran-3-amine —— C10H11F2NO
(3R)-N-ethyl-5,7-difluoro-2,3-dihydro-1-benzofuran-3-amine
—— (6R)-2,2-dimethyl-N-propan-2-yl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine —— C15H21NO2
(6R)-2,2-dimethyl-N-propan-2-yl-6,7-dihydro-3H-furo[3,2-g][1]benzofuran-6-amine
—— (3R)-5-ethoxy-N-ethyl-2,3-dihydro-1-benzofuran-3-amine —— C12H17NO2
(3R)-5-ethoxy-N-ethyl-2,3-dihydro-1-benzofuran-3-amine