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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
    —— 3-[(4-chlorophenyl)methyl-(cyclobutanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H31ClN2O7
    3-[(4-chlorophenyl)methyl-(cyclobutanecarbonyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-ethoxyacetyl)-[(2-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H29FN2O6
    3-[(2-ethoxyacetyl)-[(2-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[1-adamantylmethyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H48N2O5
    3-[1-adamantylmethyl(octanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H29F3N2O7
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2S)-2-(cyclopentylamino)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile —— C15H18N2O
    (2S)-2-(cyclopentylamino)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile
    —— 5-Methoxy-2-methyl-6,7-dinitro-2,3-dihydro-1-benzofuran —— C10H10N2O6
    5-Methoxy-2-methyl-6,7-dinitro-2,3-dihydro-1-benzofuran
    —— (3R)-3-(cyclopentylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C14H16N2O2
    (3R)-3-(cyclopentylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— (3S)-3-(cyclopentylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C14H16N2O2
    (3S)-3-(cyclopentylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— 3-[dodecanoyl(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C35H56N2O8
    3-[dodecanoyl(3-propan-2-yloxypropyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cycloheptyl(3-cyclopentylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C32H46N2O7
    3-[cycloheptyl(3-cyclopentylpropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cycloheptyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H42N2O8
    3-[cycloheptyl(5-oxohexanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cycloheptyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H44N2O7
    3-[cycloheptyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentanecarbonyl-[(4-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H35FN2O7
    3-[cyclopentanecarbonyl-[(4-fluorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3R)-3-(cyclopropylmethylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C13H14N2O2
    (3R)-3-(cyclopropylmethylamino)-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— 3-[1-adamantylmethyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C38H56N2O5
    3-[1-adamantylmethyl(dodecanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[2-(dimethylamino)ethylamino]acetonitrile —— C14H19N3O
    (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[2-(dimethylamino)ethylamino]acetonitrile
    —— (2R)-2-(1,4-diazepan-1-yl)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile —— C15H19N3O
    (2R)-2-(1,4-diazepan-1-yl)-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile
    —— (3S)-3-(1,4-diazepan-1-yl)-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C14H17N3O2
    (3S)-3-(1,4-diazepan-1-yl)-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— (3R)-3-[2-(dimethylamino)ethylamino]-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C13H17N3O2
    (3R)-3-[2-(dimethylamino)ethylamino]-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— (3S)-3-[2-(dimethylamino)ethylamino]-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C13H17N3O2
    (3S)-3-[2-(dimethylamino)ethylamino]-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile —— C15H18N2O2
    (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[[(2S)-oxolan-2-yl]methylamino]acetonitrile
    —— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[2-(dimethylamino)ethylamino]acetonitrile —— C14H19N3O
    (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[2-(dimethylamino)ethylamino]acetonitrile
    —— (3S)-6-hydroxy-3-[[(2R)-oxolan-2-yl]methylamino]-2H-1-benzofuran-3-carbonitrile —— C14H16N2O3
    (3S)-6-hydroxy-3-[[(2R)-oxolan-2-yl]methylamino]-2H-1-benzofuran-3-carbonitrile
    —— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile —— C15H18N2O2
    (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile
    —— 2-(2,3-Dihydro-1-benzofuran-5-yl)-3-(pyridin-4-ylmethyl)-1,3-thiazinan-4-one —— C18H18N2O2S
    2-(2,3-Dihydro-1-benzofuran-5-yl)-3-(pyridin-4-ylmethyl)-1,3-thiazinan-4-one
    —— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(thiophen-2-ylmethylamino)acetonitrile —— C15H14N2OS
    (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(thiophen-2-ylmethylamino)acetonitrile
    —— (3R)-6-hydroxy-3-[[(2R)-oxolan-2-yl]methylamino]-2H-1-benzofuran-3-carbonitrile —— C14H16N2O3
    (3R)-6-hydroxy-3-[[(2R)-oxolan-2-yl]methylamino]-2H-1-benzofuran-3-carbonitrile
    —— (3S)-6-hydroxy-3-[[(2S)-oxolan-2-yl]methylamino]-2H-1-benzofuran-3-carbonitrile —— C14H16N2O3
    (3S)-6-hydroxy-3-[[(2S)-oxolan-2-yl]methylamino]-2H-1-benzofuran-3-carbonitrile
    —— 4-(2-benzylidene-5-nitro-3H-1-benzofuran-3-yl)morpholin-4-ium —— C19H19N2O4+
    4-(2-benzylidene-5-nitro-3H-1-benzofuran-3-yl)morpholin-4-ium
    —— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile —— C15H18N2O2
    (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-[[(2R)-oxolan-2-yl]methylamino]acetonitrile
    —— (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(thiophen-2-ylmethylamino)acetonitrile —— C15H14N2OS
    (2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(thiophen-2-ylmethylamino)acetonitrile
    —— (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-methylpropylamino)acetonitrile —— C14H18N2O
    (2S)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(2-methylpropylamino)acetonitrile
    —— (3S)-6-hydroxy-3-(2-methylpropylamino)-2H-1-benzofuran-3-carbonitrile —— C13H16N2O2
    (3S)-6-hydroxy-3-(2-methylpropylamino)-2H-1-benzofuran-3-carbonitrile
    —— 2-methyl-1-(3-morpholin-4-ium-4-yl-5-nitro-3H-1-benzofuran-2-ylidene)propan-2-ol —— C16H21N2O5+
    2-methyl-1-(3-morpholin-4-ium-4-yl-5-nitro-3H-1-benzofuran-2-ylidene)propan-2-ol
    —— (2R)-2-anilino-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile —— C16H14N2O
    (2R)-2-anilino-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile
    —— (2S)-2-anilino-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile —— C16H14N2O
    (2S)-2-anilino-2-(2,3-dihydro-1-benzofuran-5-yl)acetonitrile
    —— (3R)-3-anilino-6-hydroxy-2H-1-benzofuran-3-carbonitrile —— C15H12N2O2
    (3R)-3-anilino-6-hydroxy-2H-1-benzofuran-3-carbonitrile
    —— ethyl (2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-carboximidate —— C14H19NO3
    ethyl (2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-carboximidate
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]aniline —— C15H15NO
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]aniline
    —— methyl (2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-carboximidate —— C13H17NO3
    methyl (2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-carboximidate
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylpropan-2-amine —— C13H19NO
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylpropan-2-amine
    —— 3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2H-1,2,4-oxadiazol-5-one —— C13H14N2O4
    3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-2H-1,2,4-oxadiazol-5-one
    —— 5-chloro-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2,4-oxadiazole —— C13H13ClN2O3
    5-chloro-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]-1,2,4-oxadiazole
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylpropan-2-amine —— C13H19NO
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-methylpropan-2-amine
    —— (1S)-N-(cyclopropylmethyl)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methylethane-1,2-diamine —— C15H22N2O
    (1S)-N-(cyclopropylmethyl)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-methylethane-1,2-diamine
    —— 3-[1-adamantylmethyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C32H42N2O5
    3-[1-adamantylmethyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(1H-1,2,4-triazol-5-ylmethyl)propan-1-amine —— C14H18N4O
    (1S)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(1H-1,2,4-triazol-5-ylmethyl)propan-1-amine
    —— (2S)-5-chloro-N-(1H-1,2,4-triazol-5-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C12H11ClN4O2
    (2S)-5-chloro-N-(1H-1,2,4-triazol-5-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(1H-1,2,4-triazol-5-ylmethyl)ethanamine —— C13H16N4O
    (1R)-1-(2,3-dihydro-1-benzofuran-5-yl)-N-(1H-1,2,4-triazol-5-ylmethyl)ethanamine
    —— (2S)-N-(1H-1,2,4-triazol-5-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C12H12N4O2
    (2S)-N-(1H-1,2,4-triazol-5-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide