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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
    —— N-(1-cyanocyclohexyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C19H24N2O3
    N-(1-cyanocyclohexyl)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— (5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione —— C15H15NO4S
    (5Z)-5-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione
    —— (5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione —— C15H15NO4S
    (5Z)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylidene]-1,3-thiazolidine-2,4-dione
    —— (2S)-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H18N2O3
    (2S)-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R)-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H18N2O3
    (2R)-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide —— C17H22F3NO4
    (3S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide
    —— ethyl 4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-4-oxobutanoate —— C18H25NO5
    ethyl 4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylamino]-4-oxobutanoate
    —— (2S)-N'-[5-(4-fluorophenyl)thiophene-2-carbonyl]-2,3-dihydro-1-benzofuran-2-carbohydrazide —— C20H15FN2O3S
    (2S)-N'-[5-(4-fluorophenyl)thiophene-2-carbonyl]-2,3-dihydro-1-benzofuran-2-carbohydrazide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-3-yl-1,2,4-oxadiazol-5-yl)propanamide —— C21H23N3O4S
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3-(3-thiophen-3-yl-1,2,4-oxadiazol-5-yl)propanamide
    —— (3aS,8bR)-3-ethyl-5-methoxy-3a-methyl-1,8b-dihydro-[1]benzofuro[2,3-c]pyrrole —— C14H17NO2
    (3aS,8bR)-3-ethyl-5-methoxy-3a-methyl-1,8b-dihydro-[1]benzofuro[2,3-c]pyrrole
    —— (E)-3-(1-benzylpyrazol-4-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide —— C25H27N3O3
    (E)-3-(1-benzylpyrazol-4-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide
    —— (E)-3-(1-benzyltriazol-4-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide —— C24H26N4O3
    (E)-3-(1-benzyltriazol-4-yl)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]prop-2-enamide
    —— 5-acetyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-2-carboxamide —— C19H21NO4S
    5-acetyl-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]thiophene-2-carboxamide
    —— (2R)-5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate —— C10H9O4-
    (2R)-5-methoxy-2,3-dihydro-1-benzofuran-2-carboxylate
    —— N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-methylphenoxy)acetamide —— C21H24N2O4
    N-[(Z)-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-2-(3-methylphenoxy)acetamide
    —— N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(5-nitro-2-oxopyridin-1-yl)acetamide —— C19H21N3O6
    N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(5-nitro-2-oxopyridin-1-yl)acetamide
    —— N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(5-nitro-2-oxopyridin-1-yl)acetamide —— C19H21N3O6
    N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-(5-nitro-2-oxopyridin-1-yl)acetamide
    —— (2R)-2-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]-4-propan-2-ylmorpholine —— C17H21N3O3
    (2R)-2-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,2,4-oxadiazol-3-yl]-4-propan-2-ylmorpholine
    —— 1-butyl-3-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]thiourea —— C17H25N3O2S
    1-butyl-3-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]thiourea
    —— 1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-ethylthiourea —— C15H21N3O2S
    1-[(Z)-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylideneamino]-3-ethylthiourea
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(1-methylpyrazol-4-yl)methanone —— C18H22N4O2
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(1-methylpyrazol-4-yl)methanone
    —— 4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-oxoethoxy]benzonitrile —— C22H24N3O3+
    4-[2-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-oxoethoxy]benzonitrile
    —— 2-(2-Chloro-4-fluorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone —— C21H22ClFN2O3
    2-(2-Chloro-4-fluorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone
    —— (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-thiophen-2-ylprop-2-en-1-one —— C20H22N2O2S
    (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-thiophen-2-ylprop-2-en-1-one
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-methoxyphenoxy)ethanone —— C22H27N2O4+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-methoxyphenoxy)ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(3-ethylphenoxy)ethanone —— C23H29N2O3+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(3-ethylphenoxy)ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-fluorophenoxy)ethanone —— C21H24FN2O3+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-(4-fluorophenoxy)ethanone
    —— [2-[[[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]amino]methyl]phenyl]methyl-dimethylazanium —— C22H29N2O3+
    [2-[[[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]amino]methyl]phenyl]methyl-dimethylazanium
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(2,6-dimethylphenoxy)ethanone —— C23H28N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(2,6-dimethylphenoxy)ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-methoxyphenyl)sulfanylethanone —— C22H26N2O3S
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(4-methoxyphenyl)sulfanylethanone
    —— N-[[2-[(dimethylamino)methyl]phenyl]methyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide —— C22H28N2O3
    N-[[2-[(dimethylamino)methyl]phenyl]methyl]-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetamide
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(3-methylphenoxy)propan-1-one —— C23H28N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(3-methylphenoxy)propan-1-one
    —— [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(5-methyl-4-propylthiophen-2-yl)methanone —— C22H29N2O2S+
    [4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-(5-methyl-4-propylthiophen-2-yl)methanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(4-methylphenyl)methylsulfanyl]ethanone —— C23H28N2O2S
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-[(4-methylphenyl)methylsulfanyl]ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-4-thiophen-2-ylbutane-1,4-dione —— C21H25N2O3S+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-4-thiophen-2-ylbutane-1,4-dione
    —— N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-1H-pyrrole-2-carbohydrazide —— C17H19N3O4
    N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-1H-pyrrole-2-carbohydrazide
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-[3-(trifluoromethyl)pyrazol-1-yl]ethanone —— C19H22F3N4O2+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-[3-(trifluoromethyl)pyrazol-1-yl]ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(4-methylphenoxy)propan-1-one —— C23H28N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(4-methylphenoxy)propan-1-one
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-phenylsulfanylethanone —— C21H25N2O2S+
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]-2-phenylsulfanylethanone
    —— 2-(3-Chlorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone —— C21H23ClN2O3
    2-(3-Chlorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone
    —— (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(5-methylthiophen-2-yl)prop-2-en-1-one —— C21H24N2O2S
    (E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-3-(5-methylthiophen-2-yl)prop-2-en-1-one
    —— (2E,4E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]hexa-2,4-dien-1-one —— C19H25N2O2+
    (2E,4E)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-4-ium-1-yl]hexa-2,4-dien-1-one
    —— 2-(2-Chloro-5-methylphenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone —— C22H25ClN2O3
    2-(2-Chloro-5-methylphenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone
    —— [4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)methanone —— C21H24N2O2S
    [4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-(5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)methanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-4-thiophen-2-ylbutane-1,4-dione —— C21H24N2O3S
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-4-thiophen-2-ylbutane-1,4-dione
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(2-methylphenoxy)ethanone —— C22H26N2O3
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-(2-methylphenoxy)ethanone
    —— 1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-thiophen-2-ylethanone —— C19H22N2O2S
    1-[4-(2,3-Dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-2-thiophen-2-ylethanone
    —— 2-(2-Chlorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone —— C21H23ClN2O3
    2-(2-Chlorophenoxy)-1-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]ethanone
    —— (2R)-N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-2-(2-fluorophenoxy)propanehydrazide —— C21H23FN2O5
    (2R)-N'-[2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]acetyl]-2-(2-fluorophenoxy)propanehydrazide
    —— (2R)-7-chloro-2-methyl-N-[(2R,3R)-2-methyloxolan-3-yl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C14H18ClNO4S
    (2R)-7-chloro-2-methyl-N-[(2R,3R)-2-methyloxolan-3-yl]-2,3-dihydro-1-benzofuran-5-sulfonamide