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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
    —— [(4aS,9bR)-9bH-dibenzofuran-4a-yl]hydrazine —— C12H12N2O
    [(4aS,9bR)-9bH-dibenzofuran-4a-yl]hydrazine
    —— [(4aR,9bR)-9bH-dibenzofuran-4a-yl]hydrazine —— C12H12N2O
    [(4aR,9bR)-9bH-dibenzofuran-4a-yl]hydrazine
    —— N-[[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-2-[(3S)-6-methyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]acetamide —— C22H22N4O4S
    N-[[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-2-[(3S)-6-methyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]acetamide
    —— 5-(furan-2-yl)-N-[[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-1,2-oxazole-3-carboxamide —— C21H17N3O5
    5-(furan-2-yl)-N-[[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-1,2-oxazole-3-carboxamide
    —— 4-methyl-N-[[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]thiadiazole-5-carboxamide —— C17H16N4O3S
    4-methyl-N-[[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]thiadiazole-5-carboxamide
    —— N-[[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-2-[(3S)-6-methyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]acetamide —— C22H22N4O4S
    N-[[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-2-[(3S)-6-methyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]acetamide
    —— 4-methyl-N-[[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]thiadiazole-5-carboxamide —— C17H16N4O3S
    4-methyl-N-[[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]thiadiazole-5-carboxamide
    —— N-[[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-2-[(3R)-6-methyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]acetamide —— C22H22N4O4S
    N-[[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2-oxazol-3-yl]methyl]-2-[(3R)-6-methyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-3-yl]acetamide
    —— N-cyclopropyl-2-[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]acetamide —— C17H18N2O3
    N-cyclopropyl-2-[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]acetamide
    —— 2-[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]-N-[[(2S)-oxolan-2-yl]methyl]acetamide —— C19H22N2O4
    2-[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]-N-[[(2S)-oxolan-2-yl]methyl]acetamide
    —— 2-[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]-N-(pyridin-4-ylmethyl)acetamide —— C20H19N3O3
    2-[5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]-N-(pyridin-4-ylmethyl)acetamide
    —— N-(5-ethylsulfanyl-1,3,4-thiadiazol-2-yl)-2-[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]acetamide —— C18H18N4O3S2
    N-(5-ethylsulfanyl-1,3,4-thiadiazol-2-yl)-2-[5-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-1,2-oxazol-3-yl]acetamide
    —— Methyl 5-{(Z)-1-[5-(2-chlorophenyl)-2-furyl]methylidene}-2A-methyl-6-oxo-2,2A-dihydro-7AH-[1]benzofuro[2,3-E]cyclopropa[D][1,3]thiazolo[3,2-A]pyrimidine-2(6H)-carboxylate —— C27H19ClN2O5S
    Methyl 5-{(Z)-1-[5-(2-chlorophenyl)-2-furyl]methylidene}-2A-methyl-6-oxo-2,2A-dihydro-7AH-[1]benzofuro[2,3-E]cyclopropa[D][1,3]thiazolo[3,2-A]pyrimidine-2(6H)-carboxylate
    —— 3-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]propanoic acid —— C12H14O4
    3-[(3R)-5-methoxy-2,3-dihydro-1-benzofuran-3-yl]propanoic acid
    —— methyl (1R,2S,3S,7E,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate —— C27H19ClN2O5S
    methyl (1R,2S,3S,7E,10R)-7-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-3-methyl-8-oxo-17-oxa-6-thia-4,9-diazapentacyclo[8.7.0.01,3.05,9.011,16]heptadeca-4,11,13,15-tetraene-2-carboxylate
    —— (3R)-3-(hydroxymethyl)-3-(methylamino)-2H-1-benzofuran-6-ol —— C10H13NO3
    (3R)-3-(hydroxymethyl)-3-(methylamino)-2H-1-benzofuran-6-ol
    —— (2R)-2-amino-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethanol —— C13H19NO3
    (2R)-2-amino-2-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]ethanol
    —— (3R)-3-amino-3-(hydroxymethyl)-2H-1-benzofuran-6-ol —— C9H11NO3
    (3R)-3-amino-3-(hydroxymethyl)-2H-1-benzofuran-6-ol
    —— (3S)-3-(hydroxymethyl)-3-(methylamino)-2H-1-benzofuran-6-ol —— C10H13NO3
    (3S)-3-(hydroxymethyl)-3-(methylamino)-2H-1-benzofuran-6-ol
    —— (3R)-3-(hydroxymethyl)-3-(propan-2-ylamino)-2H-1-benzofuran-6-ol —— C12H17NO3
    (3R)-3-(hydroxymethyl)-3-(propan-2-ylamino)-2H-1-benzofuran-6-ol
    —— 2-piperidin-1-ylethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydrochloride —— C23H30ClNO3
    2-piperidin-1-ylethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydrochloride
    —— (3R)-3-(ethylamino)-3-(hydroxymethyl)-2H-1-benzofuran-6-ol —— C11H15NO3
    (3R)-3-(ethylamino)-3-(hydroxymethyl)-2H-1-benzofuran-6-ol
    —— 2-(dimethylamino)ethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydron;chloride —— C20H26ClNO3
    2-(dimethylamino)ethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydron;chloride
    —— 2-morpholin-4-ylethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydrochloride —— C22H28ClNO4
    2-morpholin-4-ylethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydrochloride
    —— 2-(diethylamino)ethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydron;chloride —— C22H30ClNO3
    2-(diethylamino)ethyl (2Z)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;hydron;chloride
    —— (2S)-N-(3-hydroxypropyl)-N-propan-2-yl-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H21NO3
    (2S)-N-(3-hydroxypropyl)-N-propan-2-yl-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (3S)-3-[2-[(2S)-oxolan-2-yl]ethylamino]-2,3-dihydro-1-benzofuran-6-ol —— C14H19NO3
    (3S)-3-[2-[(2S)-oxolan-2-yl]ethylamino]-2,3-dihydro-1-benzofuran-6-ol
    —— (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-[(2S)-oxolan-2-yl]ethyl]ethanamine —— C16H23NO2
    (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-[(2S)-oxolan-2-yl]ethyl]ethanamine
    —— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-[(2R)-oxolan-2-yl]ethyl]ethanamine —— C16H23NO2
    (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-[(2R)-oxolan-2-yl]ethyl]ethanamine
    —— (3R)-3-[2-[(2R)-oxolan-2-yl]ethylamino]-2,3-dihydro-1-benzofuran-6-ol —— C14H19NO3
    (3R)-3-[2-[(2R)-oxolan-2-yl]ethylamino]-2,3-dihydro-1-benzofuran-6-ol
    —— (3R)-3-[(4-methyl-1,3-thiazol-2-yl)methylamino]-2,3-dihydro-1-benzofuran-6-ol —— C13H14N2O2S
    (3R)-3-[(4-methyl-1,3-thiazol-2-yl)methylamino]-2,3-dihydro-1-benzofuran-6-ol
    —— (3S)-3-[[(2R)-2-(dimethylamino)propyl]amino]-2,3-dihydro-1-benzofuran-6-ol —— C13H20N2O2
    (3S)-3-[[(2R)-2-(dimethylamino)propyl]amino]-2,3-dihydro-1-benzofuran-6-ol
    —— (2R)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C16H26N2O
    (2R)-1-N-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine
    —— (2S)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C16H26N2O
    (2S)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]-2-N,2-N-dimethylpropane-1,2-diamine
    —— (2S)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine —— C15H24N2O
    (2S)-1-N-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-2-N,2-N-dimethylpropane-1,2-diamine
    —— (2R)-2-(azepan-1-yl)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile —— C16H20N2O
    (2R)-2-(azepan-1-yl)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile
    —— (3S)-3-(azepan-1-yl)-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C15H18N2O2
    (3S)-3-(azepan-1-yl)-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— (3S)-3-[[(3R)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol —— C13H17NO4S
    (3S)-3-[[(3R)-1,1-dioxothiolan-3-yl]methylamino]-2,3-dihydro-1-benzofuran-6-ol
    —— (1S)-1-[3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
    (1S)-1-[3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
    —— (1R)-1-[3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
    (1R)-1-[3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
    —— [4-fluoro-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine —— C16H16FNO
    [4-fluoro-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]methanamine
    —— (1R)-1-[2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
    (1R)-1-[2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
    —— (1S)-1-[2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine —— C17H19NO
    (1S)-1-[2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]phenyl]ethanamine
    —— 4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H14O2
    4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
    —— 2-fluoro-5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H13FO2
    2-fluoro-5-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
    —— (1S)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine —— C16H17NO
    (1S)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]ethanamine
    —— (1R)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine —— C17H19NO
    (1R)-1-[3-(2,3-dihydro-1-benzofuran-5-yl)phenyl]-N-methylethanamine
    —— 3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H14O2
    3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
    —— 2-fluoro-4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde —— C16H13FO2
    2-fluoro-4-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]benzaldehyde
    —— 4-methyl-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]aniline —— C16H17NO
    4-methyl-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]aniline