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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
    —— 5-[[4-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]piperazin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole —— C19H26N4O2
    5-[[4-[(1R)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]piperazin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole
    —— 5-[[4-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]piperazin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole —— C19H26N4O2
    5-[[4-[(1S)-1-(2,3-dihydro-1-benzofuran-5-yl)propyl]piperazin-1-yl]methyl]-3-methyl-1,2,4-oxadiazole
    —— 4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methoxy]-3-methoxybenzaldehyde —— C20H22O5
    4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methoxy]-3-methoxybenzaldehyde
    —— 2-(2,4-dimethyl-1,3-thiazol-5-yl)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,3,4-oxadiazole —— C19H21N3O3S2
    2-(2,4-dimethyl-1,3-thiazol-5-yl)-5-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-1,3,4-oxadiazole
    —— (3R)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-methylbutanamide —— C18H23N3O2
    (3R)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-methylbutanamide
    —— (3S)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-methylbutanamide —— C18H23N3O2
    (3S)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-methylbutanamide
    —— 5-chloro-N-[(2R)-1-cyanopropan-2-yl]-N-methyl-2,3-dihydro-1-benzofuran-7-sulfonamide —— C13H15ClN2O3S
    5-chloro-N-[(2R)-1-cyanopropan-2-yl]-N-methyl-2,3-dihydro-1-benzofuran-7-sulfonamide
    —— 5-chloro-N-[(2S)-1-cyanopropan-2-yl]-N-methyl-2,3-dihydro-1-benzofuran-7-sulfonamide —— C13H15ClN2O3S
    5-chloro-N-[(2S)-1-cyanopropan-2-yl]-N-methyl-2,3-dihydro-1-benzofuran-7-sulfonamide
    —— 1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-(pyridin-3-ylmethyl)urea —— C15H13F2N3O2
    1-[(3R)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-(pyridin-3-ylmethyl)urea
    —— 5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[(5-propan-2-yl-1,3-thiazol-2-yl)methyl]-1,3,4-oxadiazol-2-amine —— C17H18N4O2S
    5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[(5-propan-2-yl-1,3-thiazol-2-yl)methyl]-1,3,4-oxadiazol-2-amine
    —— 5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(5-propan-2-yl-1,3-thiazol-2-yl)methyl]-1,3,4-oxadiazol-2-amine —— C17H18N4O2S
    5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(5-propan-2-yl-1,3-thiazol-2-yl)methyl]-1,3,4-oxadiazol-2-amine
    —— 1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-(pyridin-3-ylmethyl)urea —— C15H13F2N3O2
    1-[(3S)-4,6-difluoro-2,3-dihydro-1-benzofuran-3-yl]-3-(pyridin-3-ylmethyl)urea
    —— N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-[(3S)-oxolan-3-yl]methanamine —— C15H20ClNO2
    N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-[(3S)-oxolan-3-yl]methanamine
    —— (3R)-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine —— C15H21NOS
    (3R)-N-[(1S)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine
    —— (3R)-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine —— C15H21NOS
    (3R)-N-[(1R)-1-[(3S)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine
    —— (3R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine —— C15H21NOS
    (3R)-N-[(1R)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine
    —— 4-[[(3R)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]pyrrolidin-3-yl]methyl]morpholine —— C18H25ClN2O2
    4-[[(3R)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]pyrrolidin-3-yl]methyl]morpholine
    —— (2R)-4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-methyl-2-(1-methylpyrazol-4-yl)morpholine —— C18H22ClN3O2
    (2R)-4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-methyl-2-(1-methylpyrazol-4-yl)morpholine
    —— 3-[(3R)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-3-yl]propanamide —— C17H23ClN2O2
    3-[(3R)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-3-yl]propanamide
    —— (3R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine —— C15H21NOS
    (3R)-N-[(1S)-1-[(3R)-2,3-dihydro-1-benzofuran-3-yl]ethyl]thian-3-amine
    —— (2R,3S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-3-methylsulfonylbutan-2-amine —— C15H22ClNO3S
    (2R,3S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-3-methylsulfonylbutan-2-amine
    —— (2S)-4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-methyl-2-(1-methylpyrazol-4-yl)morpholine —— C18H22ClN3O2
    (2S)-4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-methyl-2-(1-methylpyrazol-4-yl)morpholine
    —— (3R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-cyclopropyl-1,1-dioxothiolan-3-amine —— C16H20ClNO3S
    (3R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-cyclopropyl-1,1-dioxothiolan-3-amine
    —— (2S)-4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl-methylamino]butan-2-ol —— C14H20ClNO2
    (2S)-4-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl-methylamino]butan-2-ol
    —— 3-[(3S)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-3-yl]propanamide —— C17H23ClN2O2
    3-[(3S)-1-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-3-yl]propanamide
    —— (2S,3R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-3-methylsulfonylbutan-2-amine —— C15H22ClNO3S
    (2S,3R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-3-methylsulfonylbutan-2-amine
    —— (2S,3S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-3-methylsulfonylbutan-2-amine —— C15H22ClNO3S
    (2S,3S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-3-methylsulfonylbutan-2-amine
    —— N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-[(3R)-oxolan-3-yl]methanamine —— C15H20ClNO2
    N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-N-methyl-1-[(3R)-oxolan-3-yl]methanamine
    —— (3S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-1,1-dioxothian-3-amine —— C14H18ClNO3S
    (3S)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-1,1-dioxothian-3-amine
    —— (3R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-1,1-dioxothian-3-amine —— C14H18ClNO3S
    (3R)-N-[(5-chloro-2,3-dihydro-1-benzofuran-7-yl)methyl]-1,1-dioxothian-3-amine
    —— 4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-2,6-dimethylpyrimidine-5-carbonitrile —— C19H21N3O2S
    4-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-2,6-dimethylpyrimidine-5-carbonitrile
    —— 4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-2,6-dimethylpyrimidine-5-carbonitrile —— C19H21N3O2S
    4-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methylsulfanyl]-2,6-dimethylpyrimidine-5-carbonitrile
    —— (3R)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-hydroxy-N-methyl-3-phenylbutanamide —— C19H21NO3
    (3R)-N-(2,3-dihydro-1-benzofuran-5-yl)-3-hydroxy-N-methyl-3-phenylbutanamide
    —— tert-butyl (3S)-3-cyano-4-[[(3S)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate —— C18H22N2O4
    tert-butyl (3S)-3-cyano-4-[[(3S)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate
    —— tert-butyl (3S)-3-cyano-4-[[(3R)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate —— C18H22N2O4
    tert-butyl (3S)-3-cyano-4-[[(3R)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate
    —— tert-butyl (3R)-3-cyano-4-[[(3R)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate —— C18H22N2O4
    tert-butyl (3R)-3-cyano-4-[[(3R)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate
    —— tert-butyl (3R)-3-cyano-4-[[(3S)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate —— C18H22N2O4
    tert-butyl (3R)-3-cyano-4-[[(3S)-2,3-dihydro-1-benzofuran-3-yl]amino]-3-methyl-4-oxobutanoate
    —— (3S)-5-methyl-N-[(2S)-4-pyrazol-1-ylbutan-2-yl]-2,3-dihydro-1-benzofuran-3-amine —— C16H21N3O
    (3S)-5-methyl-N-[(2S)-4-pyrazol-1-ylbutan-2-yl]-2,3-dihydro-1-benzofuran-3-amine
    —— (3R)-5-methyl-N-[(2S)-4-pyrazol-1-ylbutan-2-yl]-2,3-dihydro-1-benzofuran-3-amine —— C16H21N3O
    (3R)-5-methyl-N-[(2S)-4-pyrazol-1-ylbutan-2-yl]-2,3-dihydro-1-benzofuran-3-amine
    —— (3R)-5-methyl-N-[(2R)-4-pyrazol-1-ylbutan-2-yl]-2,3-dihydro-1-benzofuran-3-amine —— C16H21N3O
    (3R)-5-methyl-N-[(2R)-4-pyrazol-1-ylbutan-2-yl]-2,3-dihydro-1-benzofuran-3-amine
    —— (2S)-5-ethoxy-2-methyl-N-[(3R)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine —— C15H21NO3
    (2S)-5-ethoxy-2-methyl-N-[(3R)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine
    —— (2R)-5-ethoxy-2-methyl-N-[(3S)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine —— C15H21NO3
    (2R)-5-ethoxy-2-methyl-N-[(3S)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine
    —— (2S)-5-ethoxy-2-methyl-N-[(3S)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine —— C15H21NO3
    (2S)-5-ethoxy-2-methyl-N-[(3S)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine
    —— (2R)-5-ethoxy-2-methyl-N-[(3R)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine —— C15H21NO3
    (2R)-5-ethoxy-2-methyl-N-[(3R)-oxolan-3-yl]-2,3-dihydro-1-benzofuran-6-amine
    —— 5-[[[5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-1,3,4-oxadiazol-2-yl]amino]methyl]thiophene-3-carboxamide —— C16H14N4O3S
    5-[[[5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-1,3,4-oxadiazol-2-yl]amino]methyl]thiophene-3-carboxamide
    —— 5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-1,3,4-oxadiazol-2-amine —— C16H16N4O3
    5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-1,3,4-oxadiazol-2-amine
    —— 5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[(2-ethyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-amine —— C16H16N4O2S
    5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-N-[(2-ethyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-amine
    —— 5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(2-ethyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-amine —— C16H16N4O2S
    5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[(2-ethyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-amine
    —— 5-[[[5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-1,3,4-oxadiazol-2-yl]amino]methyl]thiophene-3-carboxamide —— C16H14N4O3S
    5-[[[5-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-1,3,4-oxadiazol-2-yl]amino]methyl]thiophene-3-carboxamide
    —— 5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[[5-(methoxymethyl)furan-2-yl]methyl]-1,3,4-oxadiazol-2-amine —— C17H17N3O4
    5-[(2S)-2,3-dihydro-1-benzofuran-2-yl]-N-[[5-(methoxymethyl)furan-2-yl]methyl]-1,3,4-oxadiazol-2-amine