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    首页 分子通 按分子结构分类 有机化合物 有机杂环化合物 香豆素

    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。

    相关化合物

    中文名称 英文名称 CAS号 化学式 结构式图片
    —— (2R)-N-[[2-(cyclopropylmethoxy)pyridin-4-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H20N2O3
    (2R)-N-[[2-(cyclopropylmethoxy)pyridin-4-yl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-[2-[[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methylamino]methyl]phenoxy]-N-methylacetamide —— C19H22N2O3
    2-[2-[[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methylamino]methyl]phenoxy]-N-methylacetamide
    —— 5-bromo-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyrimidin-2-amine —— C13H12BrN3O
    5-bromo-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyrimidin-2-amine
    —— 5-bromo-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyrimidin-2-amine —— C13H12BrN3O
    5-bromo-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]pyrimidin-2-amine
    —— N-[2-(4-methyl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C14H16N4O2S
    N-[2-(4-methyl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)ethyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-4-[ethyl(methylsulfonyl)amino]piperidine-1-carboxamide —— C19H29N3O4S
    N-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-4-[ethyl(methylsulfonyl)amino]piperidine-1-carboxamide
    —— N-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-4-[ethyl(methylsulfonyl)amino]piperidine-1-carboxamide —— C19H29N3O4S
    N-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-4-[ethyl(methylsulfonyl)amino]piperidine-1-carboxamide
    —— 3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-(3-methoxypropyl)-1-methylurea —— C15H22N2O3
    3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-(3-methoxypropyl)-1-methylurea
    —— 3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-(3-methoxypropyl)-1-methylurea —— C15H22N2O3
    3-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-(3-methoxypropyl)-1-methylurea
    —— N-[(4-ethyl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C14H16N4O2S
    N-[(4-ethyl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-1-(pyridin-2-ylmethyl)urea —— C19H23N3O3
    3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1-methyl-1-(pyridin-2-ylmethyl)urea
    —— (2R)-N-[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18N4O3
    (2R)-N-[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 2-chloro-1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone —— C11H11ClO2
    2-chloro-1-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone
    —— (2S)-N-[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H18N4O3
    (2S)-N-[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(S)-amino-[(2S)-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C11H14N2O3
    N-[(S)-amino-[(2S)-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— N-[(R)-amino-[(2S)-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C11H14N2O3
    N-[(R)-amino-[(2S)-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— N-[(R)-amino-[(2R)-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide —— C11H14N2O3
    N-[(R)-amino-[(2R)-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]acetamide
    —— (2R)-N-prop-2-enyl-N-(2,2,2-trifluoroethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H14F3NO2
    (2R)-N-prop-2-enyl-N-(2,2,2-trifluoroethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-prop-2-enyl-N-(2,2,2-trifluoroethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H14F3NO2
    (2S)-N-prop-2-enyl-N-(2,2,2-trifluoroethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-propan-2-ylthiophene-2-carboxamide —— C19H23NO3S
    N-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-propan-2-ylthiophene-2-carboxamide
    —— N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-propan-2-ylthiophene-2-carboxamide —— C19H23NO3S
    N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-propan-2-ylthiophene-2-carboxamide
    —— (7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-7-(trifluoromethyl)furo[2,3-f][1,3]benzodioxol-6-one —— C18H13F3O7
    (7R)-7-(4-hydroxy-3,5-dimethoxyphenyl)-7-(trifluoromethyl)furo[2,3-f][1,3]benzodioxol-6-one
    —— (7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-7-(trifluoromethyl)furo[2,3-f][1,3]benzodioxol-6-one —— C18H13F3O7
    (7S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-7-(trifluoromethyl)furo[2,3-f][1,3]benzodioxol-6-one
    —— 3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(4-fluorophenyl)methyl]-1-prop-2-ynylurea —— C20H19FN2O2
    3-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-1-[(4-fluorophenyl)methyl]-1-prop-2-ynylurea
    —— 1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[[5-methoxy-2-(pyridin-2-ylmethoxy)phenyl]methyl]methanamine —— C23H24N2O3
    1-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[[5-methoxy-2-(pyridin-2-ylmethoxy)phenyl]methyl]methanamine
    —— 1-(2-chloropyridin-3-yl)-3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]urea —— C18H20ClN3O3
    1-(2-chloropyridin-3-yl)-3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]urea
    —— N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-nitropyrazol-1-yl)propanamide —— C17H20N4O5
    N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-nitropyrazol-1-yl)propanamide
    —— N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethoxyphenyl)propanamide —— C22H27NO4
    N-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-(4-ethoxyphenyl)propanamide
    —— N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine —— C18H28N2O3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2S)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2S)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine —— C17H26N2O3
    N-[[(2R)-5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine —— C18H28N2O3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine
    —— 1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-1-hydroxypropan-2-yl]urea —— C15H22N2O4
    1-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-1-hydroxypropan-2-yl]urea
    —— 1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-1-hydroxypropan-2-yl]urea —— C15H22N2O4
    1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2R)-1-hydroxypropan-2-yl]urea
    —— 1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2S)-1-hydroxypropan-2-yl]urea —— C15H22N2O4
    1-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-3-[(2S)-1-hydroxypropan-2-yl]urea
    —— (2S)-5-chloro-N,N-bis(cyanomethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C13H10ClN3O2
    (2S)-5-chloro-N,N-bis(cyanomethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-5-chloro-N,N-bis(cyanomethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C13H10ClN3O2
    (2R)-5-chloro-N,N-bis(cyanomethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 4-chloro-2-(2,4-difluorophenyl)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]pyridazin-3-one —— C22H20ClF2N3O3
    4-chloro-2-(2,4-difluorophenyl)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]pyridazin-3-one
    —— 4-chloro-2-(2,4-difluorophenyl)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]pyridazin-3-one —— C22H20ClF2N3O3
    4-chloro-2-(2,4-difluorophenyl)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]pyridazin-3-one
    —— (2R)-N-[[(2R)-oxolan-2-yl]methyl]-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H22N2O3
    (2R)-N-[[(2R)-oxolan-2-yl]methyl]-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methyl-1,3-thiazole-4-carboxamide —— C17H20N2O3S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methyl-1,3-thiazole-4-carboxamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methyl-1,3-thiazole-4-carboxamide —— C17H20N2O3S
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-methyl-1,3-thiazole-4-carboxamide
    —— 3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(furan-2-ylmethyl)-1-methylurea —— C19H24N2O4
    3-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(furan-2-ylmethyl)-1-methylurea
    —— (2S)-N-[[(2S)-oxolan-2-yl]methyl]-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H22N2O3
    (2S)-N-[[(2S)-oxolan-2-yl]methyl]-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide