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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
    —— 6-[2-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)vinyl]-5-nitro-2,4-pyrimidinediol —— C15H13N3O5
    6-[2-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)vinyl]-5-nitro-2,4-pyrimidinediol
    —— (4E)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione —— C23H19NO5S
    (4E)-1-(furan-2-ylmethyl)-4-[hydroxy-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-5-thiophen-2-ylpyrrolidine-2,3-dione
    —— [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(4-chlorophenyl)carbamate —— C17H15ClN2O3
    [(E)-1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino] N-(4-chlorophenyl)carbamate
    —— (Z)-N-[(4-chlorophenyl)methoxy]-1-(2,3-dihydro-1-benzofuran-5-yl)ethanimine —— C17H16ClNO2
    (Z)-N-[(4-chlorophenyl)methoxy]-1-(2,3-dihydro-1-benzofuran-5-yl)ethanimine
    —— [(Z)-2,3-dihydro-1-benzofuran-5-ylmethylideneamino] N-(4-chlorophenyl)carbamate —— C16H13ClN2O3
    [(Z)-2,3-dihydro-1-benzofuran-5-ylmethylideneamino] N-(4-chlorophenyl)carbamate
    —— (3Z)-6-methoxy-1-benzofuran-3(2H)-one O-(2-chloroacetyl)oxime —— C11H10ClNO4
    (3Z)-6-methoxy-1-benzofuran-3(2H)-one O-(2-chloroacetyl)oxime
    —— (3R)-6-methoxy-3,4-dimethyl-2,3-dihydro-1-benzofuran-5-ol —— C11H14O3
    (3R)-6-methoxy-3,4-dimethyl-2,3-dihydro-1-benzofuran-5-ol
    —— 4-{[(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]methyl}-2-phenyl-1,3-thiazole —— C20H19NO2S
    4-{[(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]methyl}-2-phenyl-1,3-thiazole
    —— 6-{[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]methyl}-N-phenyl-1,3,5-triazine-2,4-diamine —— C20H21N5O2
    6-{[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]methyl}-N-phenyl-1,3,5-triazine-2,4-diamine
    —— 2-[(3S)-3-methyl-2H-1-benzofuran-3-yl]acetaldehyde —— C11H12O2
    2-[(3S)-3-methyl-2H-1-benzofuran-3-yl]acetaldehyde
    —— 2-[(3R)-3-methyl-2H-1-benzofuran-3-yl]acetaldehyde —— C11H12O2
    2-[(3R)-3-methyl-2H-1-benzofuran-3-yl]acetaldehyde
    —— tert-butyl N-[(2R)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]-3-oxopropyl]carbamate —— C19H27NO4
    tert-butyl N-[(2R)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]-3-oxopropyl]carbamate
    —— (3S)-3-(aminomethyl)-4-(2,3-dihydro-1-benzofuran-5-yl)butan-2-one —— C13H17NO2
    (3S)-3-(aminomethyl)-4-(2,3-dihydro-1-benzofuran-5-yl)butan-2-one
    —— (3R)-3-(aminomethyl)-4-(2,3-dihydro-1-benzofuran-5-yl)butan-2-one —— C13H17NO2
    (3R)-3-(aminomethyl)-4-(2,3-dihydro-1-benzofuran-5-yl)butan-2-one
    —— tert-butyl N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-oxopropyl]carbamate —— C17H23NO4
    tert-butyl N-[(2R)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-oxopropyl]carbamate
    —— tert-butyl N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-oxopropyl]carbamate —— C17H23NO4
    tert-butyl N-[(2S)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-oxopropyl]carbamate
    —— tert-butyl N-[(2S)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]-3-oxopropyl]carbamate —— C19H27NO4
    tert-butyl N-[(2S)-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)methyl]-3-oxopropyl]carbamate
    —— 1-(2,2-dimethyl-3H-1-benzofuran-5-yl)pyrazol-3-amine —— C13H15N3O
    1-(2,2-dimethyl-3H-1-benzofuran-5-yl)pyrazol-3-amine
    —— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[propanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C22H27F3N2O7
    4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[propanoyl(2,2,2-trifluoroethyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(4-chlorophenyl)methyl-dodecanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C36H49ClN2O7
    3-[(4-chlorophenyl)methyl-dodecanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[1-adamantylmethyl(pentanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H44N2O7
    3-[1-adamantylmethyl(pentanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-cyclopentylpropanoyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H40N2O5
    3-[3-cyclopentylpropanoyl(3-methylbutyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[acetyl-[(4-methylphenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H30N2O7
    3-[acetyl-[(4-methylphenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[acetyl(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C24H32N2O8
    3-[acetyl(3-ethoxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[butanoyl-[(3,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H28Cl2N2O5
    3-[butanoyl-[(3,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— N-(2,3-dihydro-1-benzofuran-5-ylmethyl)cyclopropanamine —— C12H15NO
    N-(2,3-dihydro-1-benzofuran-5-ylmethyl)cyclopropanamine
    —— 3-[acetyl-[(2,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H28Cl2N2O7
    3-[acetyl-[(2,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentanecarbonyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O8
    3-[cyclopentanecarbonyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-ethoxypropyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H38N2O9
    3-[3-ethoxypropyl(oxolane-3-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (Z)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(furan-2-yl)prop-2-en-1-amine —— C16H17NO2
    (Z)-N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(furan-2-yl)prop-2-en-1-amine
    —— (Z)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(furan-2-yl)prop-2-en-1-amine —— C16H17NO2
    (Z)-N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-3-(furan-2-yl)prop-2-en-1-amine
    —— 3-[cyclohexyl(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O7
    3-[cyclohexyl(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-ethoxypropyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H38N2O9
    3-[3-ethoxypropyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl (Z)-3-(1,3-thiazol-4-yl)prop-2-enoate —— C15H12FNO3S
    [(2S)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl (Z)-3-(1,3-thiazol-4-yl)prop-2-enoate
    —— [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl (Z)-3-(1,3-thiazol-4-yl)prop-2-enoate —— C15H12FNO3S
    [(2R)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl (Z)-3-(1,3-thiazol-4-yl)prop-2-enoate
    —— 3-[cyclohexyl(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H38N2O8
    3-[cyclohexyl(5-oxohexanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (Z)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]prop-2-enenitrile —— C20H16ClF3N2O2
    (Z)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]prop-2-enenitrile
    —— (Z)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]prop-2-enenitrile —— C20H16ClF3N2O2
    (Z)-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-7-yl]prop-2-enenitrile
    —— [(Z)-but-2-enyl] 2,3-dihydro-1-benzofuran-5-carboxylate —— C13H14O3
    [(Z)-but-2-enyl] 2,3-dihydro-1-benzofuran-5-carboxylate
    —— (2Z,4Z)-N-(2,3-dihydro-1-benzofuran-5-yl)hexa-2,4-dienamide —— C14H15NO2
    (2Z,4Z)-N-(2,3-dihydro-1-benzofuran-5-yl)hexa-2,4-dienamide
    —— (2Z,4E)-N-(2,3-dihydro-1-benzofuran-5-yl)hexa-2,4-dienamide —— C14H15NO2
    (2Z,4E)-N-(2,3-dihydro-1-benzofuran-5-yl)hexa-2,4-dienamide
    —— (2E,4Z)-N-(2,3-dihydro-1-benzofuran-5-yl)hexa-2,4-dienamide —— C14H15NO2
    (2E,4Z)-N-(2,3-dihydro-1-benzofuran-5-yl)hexa-2,4-dienamide
    —— 2,3-dihydro-1-benzofuran-5-yl-[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methanone —— C22H24N2O2
    2,3-dihydro-1-benzofuran-5-yl-[4-[(Z)-3-phenylprop-2-enyl]piperazin-1-yl]methanone
    —— 3-[cyclopentyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H34N2O7
    3-[cyclopentyl(cyclopropanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 8-formyl-3-[hexyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H38N2O8
    8-formyl-3-[hexyl(3-methoxypropanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (Z)-1-(2,3-dihydro-1-benzofuran-5-yl)-3-(1-methylpyrazol-4-yl)prop-2-en-1-one —— C15H14N2O2
    (Z)-1-(2,3-dihydro-1-benzofuran-5-yl)-3-(1-methylpyrazol-4-yl)prop-2-en-1-one
    —— 2-[(Z)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]-1H-pyrimidin-6-one —— C14H12N2O2
    2-[(Z)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]-1H-pyrimidin-6-one
    —— (E)-2-cyano-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[1-(2-methoxyethyl)-2,5-dimethylpyrrol-3-yl]prop-2-enamide —— C21H23N3O3
    (E)-2-cyano-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-3-[1-(2-methoxyethyl)-2,5-dimethylpyrrol-3-yl]prop-2-enamide
    —— (E)-2-cyano-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[1-(2-methoxyethyl)-2,5-dimethylpyrrol-3-yl]prop-2-enamide —— C21H23N3O3
    (E)-2-cyano-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-3-[1-(2-methoxyethyl)-2,5-dimethylpyrrol-3-yl]prop-2-enamide
    —— 3-[(5E)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-3,4-dihydro-2H-pyridin-6-yl]pyridine —— C19H18N2O
    3-[(5E)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-3,4-dihydro-2H-pyridin-6-yl]pyridine