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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
    —— (2S)-N-(3-ethyl-1-methyl-2H-pyrazolo[3,4-c]pyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17N5O2
    (2S)-N-(3-ethyl-1-methyl-2H-pyrazolo[3,4-c]pyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(3-ethyl-1-methyl-2H-pyrazolo[3,4-c]pyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17N5O2
    (2R)-N-(3-ethyl-1-methyl-2H-pyrazolo[3,4-c]pyrazol-4-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(1S)-2-methyl-1-(3-methylpyridin-2-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H22N2O2
    (2R)-N-[(1S)-2-methyl-1-(3-methylpyridin-2-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-(3-carbamoyl-5-methylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H14N2O3S
    (2S)-N-(3-carbamoyl-5-methylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-[(2S)-2-hydroxy-2-phenylpropyl]urea —— C20H24N2O3
    1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-[(2S)-2-hydroxy-2-phenylpropyl]urea
    —— (2S)-N-[(1R)-2-methyl-1-(3-methylpyridin-2-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H22N2O2
    (2S)-N-[(1R)-2-methyl-1-(3-methylpyridin-2-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(1R)-2-methyl-1-(3-methylpyridin-2-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C19H22N2O2
    (2R)-N-[(1R)-2-methyl-1-(3-methylpyridin-2-yl)propyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-(3-carbamoyl-5-methylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H14N2O3S
    (2R)-N-(3-carbamoyl-5-methylthiophen-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-[(2R)-2-hydroxy-2-phenylpropyl]urea —— C20H24N2O3
    1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-3-[(2R)-2-hydroxy-2-phenylpropyl]urea
    —— (3S,8aR)-2-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine —— C16H22N2O3S
    (3S,8aR)-2-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine
    —— (3R,8aR)-2-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine —— C16H22N2O3S
    (3R,8aR)-2-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine
    —— (3S)-N-[(4-cyano-2-fluorophenyl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H13FN2O2
    (3S)-N-[(4-cyano-2-fluorophenyl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— (3R)-N-[(4-cyano-2-fluorophenyl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C17H13FN2O2
    (3R)-N-[(4-cyano-2-fluorophenyl)methyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[3-(methylamino)-7,8-dihydro-5H-pyrido[4,3-c]pyridazin-6-yl]methanone —— C17H18N4O2
    [(2S)-2,3-dihydro-1-benzofuran-2-yl]-[3-(methylamino)-7,8-dihydro-5H-pyrido[4,3-c]pyridazin-6-yl]methanone
    —— [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[3-(methylamino)-7,8-dihydro-5H-pyrido[4,3-c]pyridazin-6-yl]methanone —— C17H18N4O2
    [(2R)-2,3-dihydro-1-benzofuran-2-yl]-[3-(methylamino)-7,8-dihydro-5H-pyrido[4,3-c]pyridazin-6-yl]methanone
    —— ethyl (1S,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl-[(1,5-dimethylpyrazol-3-yl)methyl]amino]methyl]cyclopropane-1-carboxylate —— C22H27N3O4
    ethyl (1S,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl-[(1,5-dimethylpyrazol-3-yl)methyl]amino]methyl]cyclopropane-1-carboxylate
    —— ethyl (1R,2R)-2-[[2,3-dihydro-1-benzofuran-5-ylmethyl-(1,5-dimethylpyrazole-3-carbonyl)amino]methyl]cyclopropane-1-carboxylate —— C22H27N3O4
    ethyl (1R,2R)-2-[[2,3-dihydro-1-benzofuran-5-ylmethyl-(1,5-dimethylpyrazole-3-carbonyl)amino]methyl]cyclopropane-1-carboxylate
    —— N-[(1,5-dimethylpyrazol-3-yl)methyl]-N-[(2,5-dimethylpyrazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C21H25N5O2
    N-[(1,5-dimethylpyrazol-3-yl)methyl]-N-[(2,5-dimethylpyrazol-3-yl)methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— tert-butyl N-(2,3-dihydro-1-benzofuran-5-carbonyl)-N-[3-(1,3-thiazol-2-ylmethylamino)propyl]carbamate —— C21H27N3O4S
    tert-butyl N-(2,3-dihydro-1-benzofuran-5-carbonyl)-N-[3-(1,3-thiazol-2-ylmethylamino)propyl]carbamate
    —— ethyl (1R,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl-[(1,3,5-trimethylpyrazol-4-yl)methyl]amino]methyl]cyclopropane-1-carboxylate —— C23H29N3O4
    ethyl (1R,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl-[(1,3,5-trimethylpyrazol-4-yl)methyl]amino]methyl]cyclopropane-1-carboxylate
    —— ethyl (1R,2R)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl-[(1,3,5-trimethylpyrazol-4-yl)methyl]amino]methyl]cyclopropane-1-carboxylate —— C23H29N3O4
    ethyl (1R,2R)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl-[(1,3,5-trimethylpyrazol-4-yl)methyl]amino]methyl]cyclopropane-1-carboxylate
    —— N-(2-acetamidoethyl)-N'-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]butanediamide —— C18H25N3O4
    N-(2-acetamidoethyl)-N'-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]butanediamide
    —— (8aR)-2-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine —— C15H20N2O3S
    (8aR)-2-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine
    —— [(2S)-1-[6-(2,3-dihydro-1-benzofuran-5-ylmethylamino)pyrimidin-4-yl]pyrrolidin-2-yl]methanol —— C18H22N4O2
    [(2S)-1-[6-(2,3-dihydro-1-benzofuran-5-ylmethylamino)pyrimidin-4-yl]pyrrolidin-2-yl]methanol
    —— [(2R)-1-[6-(2,3-dihydro-1-benzofuran-5-ylmethylamino)pyrimidin-4-yl]pyrrolidin-2-yl]methanol —— C18H22N4O2
    [(2R)-1-[6-(2,3-dihydro-1-benzofuran-5-ylmethylamino)pyrimidin-4-yl]pyrrolidin-2-yl]methanol
    —— 1-[2-(dimethylamino)ethyl]-3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-(2-methoxyethyl)urea —— C18H29N3O3
    1-[2-(dimethylamino)ethyl]-3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-(2-methoxyethyl)urea
    —— 3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(2-morpholin-4-ylethyl)urea —— C18H27N3O3
    3-[(3R)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(2-morpholin-4-ylethyl)urea
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine —— C18H28N2O3
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-[(2R)-4-methylmorpholin-2-yl]methanamine
    —— 3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(2-morpholin-4-ylethyl)urea —— C18H27N3O3
    3-[(3S)-6,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl]-1-methyl-1-(2-morpholin-4-ylethyl)urea
    —— (2R)-N-[(3S)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17NO4S
    (2R)-N-[(3S)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(3S)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17NO4S
    (2S)-N-[(3S)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-N-[(3R)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17NO4S
    (2S)-N-[(3R)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(3R)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H17NO4S
    (2R)-N-[(3R)-1,1-dioxothiolan-3-yl]-N-prop-2-ynyl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— 3-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-1-[[(2S)-oxolan-2-yl]methyl]-1-prop-2-ynylurea —— C24H26N2O3
    3-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-1-[[(2S)-oxolan-2-yl]methyl]-1-prop-2-ynylurea
    —— 3-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-1-[[(2R)-oxolan-2-yl]methyl]-1-prop-2-ynylurea —— C24H26N2O3
    3-[[4-(2,3-dihydro-1-benzofuran-5-yl)phenyl]methyl]-1-[[(2R)-oxolan-2-yl]methyl]-1-prop-2-ynylurea
    —— (2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxooxolane-2-carboxamide —— C21H25NO4
    (2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxooxolane-2-carboxamide
    —— (2S)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide —— C19H22ClN3O3
    (2S)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide
    —— (2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide —— C19H22ClN3O3
    (2R)-N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide
    —— (2S)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxooxolane-2-carboxamide —— C21H25NO4
    (2S)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-5-oxooxolane-2-carboxamide
    —— N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-methylsulfonylacetamide —— C17H20ClN3O4S
    N-[(4-chloro-1-methylpyrazol-3-yl)methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)-2-methylsulfonylacetamide
    —— (2R)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide —— C21H27NO3
    (2R)-N-[[(1R)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide
    —— (2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide —— C21H27NO3
    (2R)-N-[[(1S)-cyclohex-3-en-1-yl]methyl]-N-(2,3-dihydro-1-benzofuran-5-ylmethyl)oxolane-2-carboxamide
    —— ethyl (1S,2S)-2-[[2,3-dihydro-1-benzofuran-7-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate —— C25H29NO4
    ethyl (1S,2S)-2-[[2,3-dihydro-1-benzofuran-7-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate
    —— N-[(2-methylphenyl)methyl]-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C25H25NO2
    N-[(2-methylphenyl)methyl]-N-[(1R)-1-phenylethyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— N-(cyclohexylmethyl)-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide —— C21H25NO3
    N-(cyclohexylmethyl)-N-(furan-2-ylmethyl)-2,3-dihydro-1-benzofuran-7-carboxamide
    —— N-[(2-methylphenyl)methyl]-N-propan-2-yl-2,3-dihydro-1-benzofuran-7-carboxamide —— C20H23NO2
    N-[(2-methylphenyl)methyl]-N-propan-2-yl-2,3-dihydro-1-benzofuran-7-carboxamide
    —— ethyl (1R,2R)-2-[[2,3-dihydro-1-benzofuran-7-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate —— C25H29NO4
    ethyl (1R,2R)-2-[[2,3-dihydro-1-benzofuran-7-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate
    —— N-cyclohexyl-N-[(2-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C23H27NO2
    N-cyclohexyl-N-[(2-methylphenyl)methyl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— ethyl (1S,2S)-2-[[butyl(2,3-dihydro-1-benzofuran-7-carbonyl)amino]methyl]cyclopropane-1-carboxylate —— C20H27NO4
    ethyl (1S,2S)-2-[[butyl(2,3-dihydro-1-benzofuran-7-carbonyl)amino]methyl]cyclopropane-1-carboxylate
    —— ethyl (1S,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate —— C25H29NO4
    ethyl (1S,2S)-2-[[2,3-dihydro-1-benzofuran-5-carbonyl(3-phenylpropyl)amino]methyl]cyclopropane-1-carboxylate