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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-cyclopropyl-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]propanamide —— C22H29N3O2
    N-cyclopropyl-3-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(1,3,5-trimethylpyrazol-4-yl)methyl]propanamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[(4-methylphenyl)methyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H30N2O5
    4-hydroxy-N-(2-hydroxyethyl)-3-[(4-methylphenyl)methyl-propanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (3S,8aR)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine —— C17H24N2O
    (3S,8aR)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine
    —— (3S,8aS)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine —— C17H24N2O
    (3S,8aS)-2-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-methyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[pent-2-enoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O6
    4-hydroxy-N-(2-hydroxyethyl)-3-[pent-2-enoyl(3-propan-2-yloxypropyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,5-dimethylpyrazol-1-yl)acetamide —— C16H19N3O2
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,5-dimethylpyrazol-1-yl)acetamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[oxolan-2-ylmethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H36N2O8
    4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3-[oxolan-2-ylmethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopropylmethyl(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H30N2O8
    3-[cyclopropylmethyl(2-oxobutanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[benzyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H38N2O7
    3-[benzyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 1-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)-3-piperidin-1-ium-1-ylpropan-1-one —— C17H24NO2+
    1-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)-3-piperidin-1-ium-1-ylpropan-1-one
    —— 1-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)-3-piperidin-1-ylpropan-1-one —— C17H23NO2
    1-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)-3-piperidin-1-ylpropan-1-one
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-(3-methoxyphenyl)ethyl-(2-methylpropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H34N2O6
    4-hydroxy-N-(2-hydroxyethyl)-3-[2-(3-methoxyphenyl)ethyl-(2-methylpropanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,5-dimethylpyrazol-1-yl)acetamide —— C16H19N3O2
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,5-dimethylpyrazol-1-yl)acetamide
    —— 4-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)butan-2-one —— C13H16O2
    4-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)butan-2-one
    —— 3-[(2-fluorophenyl)methyl-propanoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H29FN2O7
    3-[(2-fluorophenyl)methyl-propanoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[1-adamantylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C33H44N2O5
    3-[1-adamantylmethyl-(2-cyclopentylacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]acetamide —— C15H17N3O3
    2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]acetamide
    —— 2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]acetamide —— C15H17N3O3
    2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]acetamide
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,4,5-trimethylpyrazol-1-yl)acetamide —— C17H21N3O2
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,4,5-trimethylpyrazol-1-yl)acetamide
    —— N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,4,5-trimethylpyrazol-1-yl)acetamide —— C17H21N3O2
    N-[[(2S)-2,3-dihydro-1-benzofuran-2-yl]methyl]-2-(3,4,5-trimethylpyrazol-1-yl)acetamide
    —— (1R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine —— C22H26N2O2S2
    (1R)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine
    —— (1S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine —— C22H26N2O2S2
    (1S)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine
    —— (1R,2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methyl-1,2-oxazol-5-yl)methyl]cyclopentan-1-amine —— C22H30N2O3
    (1R,2S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-2-[(3-methyl-1,2-oxazol-5-yl)methyl]cyclopentan-1-amine
    —— (1R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine —— C22H26N2O2S2
    (1R)-N-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine
    —— 2-[(3S,8aS)-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-3-yl]ethanol —— C21H32N2O3
    2-[(3S,8aS)-2-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-3-yl]ethanol
    —— N'-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-2-ylmethyl)ethane-1,2-diamine —— C22H31N3O2
    N'-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-2-ylmethyl)ethane-1,2-diamine
    —— (1S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine —— C22H26N2O2S2
    (1S)-N-[[(2S)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-1-(4-methyl-1,3-thiazol-2-yl)-2-thiophen-3-ylethanamine
    —— N'-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-3-ylmethyl)ethane-1,2-diamine —— C22H31N3O2
    N'-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-3-ylmethyl)ethane-1,2-diamine
    —— N'-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-2-ylmethyl)ethane-1,2-diamine —— C22H31N3O2
    N'-[[(2R)-5-ethoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl]methyl]-N,N-dimethyl-N'-(pyridin-2-ylmethyl)ethane-1,2-diamine
    —— 1-[4-[(1-ethylpyrazol-4-yl)methyl]piperazin-1-yl]-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone —— C21H28N4O2
    1-[4-[(1-ethylpyrazol-4-yl)methyl]piperazin-1-yl]-2-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone
    —— 1-[4-[(1-ethylpyrazol-4-yl)methyl]piperazin-1-yl]-2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone —— C21H28N4O2
    1-[4-[(1-ethylpyrazol-4-yl)methyl]piperazin-1-yl]-2-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]ethanone
    —— N-[(S)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide —— C26H29N3O2S
    N-[(S)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide
    —— N-[(S)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide —— C23H29N3O2
    N-[(S)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide
    —— N-[(S)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide —— C26H29N3O2S
    N-[(S)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide
    —— (2S)-N-(3-methoxypropyl)-2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide —— C24H29NO4
    (2S)-N-(3-methoxypropyl)-2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide —— C23H29N3O2
    N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide
    —— 2-cyclopentyl-N-[(R)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide —— C28H37N3O2
    2-cyclopentyl-N-[(R)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide
    —— 7-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-propan-2-yl-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepin-4-one —— C21H27N3O2
    7-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-propan-2-yl-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepin-4-one
    —— N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide —— C26H29N3O2S
    N-[(R)-[1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide
    —— N-(3-methoxypropyl)-2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-4,5,6,7-tetrahydroindazole-3-carboxamide —— C23H31N3O3
    N-(3-methoxypropyl)-2-methyl-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-4,5,6,7-tetrahydroindazole-3-carboxamide
    —— N-(3-fluorophenyl)-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7-dihydro-4H-[1,2]oxazolo[4,5-c]pyridin-3-amine —— C22H22FN3O2
    N-(3-fluorophenyl)-5-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-6,7-dihydro-4H-[1,2]oxazolo[4,5-c]pyridin-3-amine
    —— N-cyclopentyl-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-(pyridin-2-ylmethyl)propanamide —— C23H28N2O2
    N-cyclopentyl-3-[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]-N-(pyridin-2-ylmethyl)propanamide
    —— (3R,4R)-N,N-dimethyl-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-4-(2-piperidin-1-ylpyrimidin-4-yl)pyrrolidine-3-carboxamide —— C26H35N5O2
    (3R,4R)-N,N-dimethyl-1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-4-(2-piperidin-1-ylpyrimidin-4-yl)pyrrolidine-3-carboxamide
    —— N-[(R)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide —— C26H29N3O2S
    N-[(R)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]thiophene-2-carboxamide
    —— N-(3-methoxypropyl)-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide —— C19H22F3N3O3
    N-(3-methoxypropyl)-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide
    —— 7-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-propan-2-yl-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepin-4-one —— C21H27N3O2
    7-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-propan-2-yl-5,6,8,9-tetrahydro-3H-pyrimido[4,5-d]azepin-4-one
    —— N-(3-methoxypropyl)-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide —— C19H22F3N3O3
    N-(3-methoxypropyl)-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide
    —— N-[(S)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide —— C23H29N3O2
    N-[(S)-[1-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-4-yl]-pyridin-2-ylmethyl]acetamide
    —— 3-methoxy-N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide —— C25H33N3O3
    3-methoxy-N-[(S)-[(3S)-1-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]piperidin-3-yl]-pyridin-2-ylmethyl]propanamide
    —— (2R)-N-[(4-methoxyphenyl)methyl]-2-methyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide —— C24H24N2O3
    (2R)-N-[(4-methoxyphenyl)methyl]-2-methyl-N-(pyridin-3-ylmethyl)-2,3-dihydro-1-benzofuran-5-carboxamide