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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-[cyclopentanecarbonyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H34N2O5
    3-[cyclopentanecarbonyl-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(octanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H44N2O7
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[3-methylbutyl(octanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[acetyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O8
    3-[acetyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[3-cyclopentylpropanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H36N2O6
    3-[3-cyclopentylpropanoyl(2-methoxyethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-octanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C34H44N2O8
    8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3-[2-(2-methoxyphenyl)ethyl-octanoylamino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[butanoyl-[(2,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H28Cl2N2O5
    3-[butanoyl-[(2,4-dichlorophenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[dodecanoyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C35H54N2O8
    3-[dodecanoyl(3-propan-2-yloxypropyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2,4-dichlorophenyl)methyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H28Cl2N2O6
    3-[(2,4-dichlorophenyl)methyl-(oxolane-2-carbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— N-[(6-methoxy-1-benzofuran-3-ylidene)amino]-2-(2-methylphenoxy)acetamide —— C18H18N2O4
    N-[(6-methoxy-1-benzofuran-3-ylidene)amino]-2-(2-methylphenoxy)acetamide
    —— N-[(5-methoxy-1-benzofuran-3-ylidene)amino]-2-(4-methylphenoxy)acetamide —— C18H18N2O4
    N-[(5-methoxy-1-benzofuran-3-ylidene)amino]-2-(4-methylphenoxy)acetamide
    —— N-(1-benzofuran-3-ylideneamino)-2-(3-chlorophenoxy)propanamide —— C17H15ClN2O3
    N-(1-benzofuran-3-ylideneamino)-2-(3-chlorophenoxy)propanamide
    —— N-[(5-methoxy-1-benzofuran-3-ylidene)amino]-2-(2-methylphenoxy)acetamide —— C18H18N2O4
    N-[(5-methoxy-1-benzofuran-3-ylidene)amino]-2-(2-methylphenoxy)acetamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[3-methylbutyl(pentanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H36N2O5
    4-hydroxy-N-(2-hydroxyethyl)-3-[3-methylbutyl(pentanoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 2-(3-chlorophenoxy)-N-[(6-methyl-1-benzofuran-3-ylidene)amino]propanamide —— C18H17ClN2O3
    2-(3-chlorophenoxy)-N-[(6-methyl-1-benzofuran-3-ylidene)amino]propanamide
    —— N-(1-benzofuran-3-ylideneamino)-2-(4-chlorophenoxy)acetamide —— C16H13ClN2O3
    N-(1-benzofuran-3-ylideneamino)-2-(4-chlorophenoxy)acetamide
    —— 5-[[1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino]oxymethyl]-N,N-dimethylfuran-2-sulfonamide —— C17H20N2O5S
    5-[[1-(2,3-dihydro-1-benzofuran-5-yl)ethylideneamino]oxymethyl]-N,N-dimethylfuran-2-sulfonamide
    —— 3-[cycloheptyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H40N2O5
    3-[cycloheptyl(hept-6-enoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— Ethyl 2-cyano-3-(2,3-dihydro-1-benzofuran-3-ylamino)prop-2-enoate —— C14H14N2O3
    Ethyl 2-cyano-3-(2,3-dihydro-1-benzofuran-3-ylamino)prop-2-enoate
    —— N-(2,3-dihydro-1-benzofuran-3-yl)-3-pyrazin-2-ylprop-2-enamide —— C15H13N3O2
    N-(2,3-dihydro-1-benzofuran-3-yl)-3-pyrazin-2-ylprop-2-enamide
    —— N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-3-(1,3-thiazol-4-yl)prop-2-enamide —— C15H14N2O2S
    N-(2,3-dihydro-1-benzofuran-2-ylmethyl)-3-(1,3-thiazol-4-yl)prop-2-enamide
    —— 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)acetamide —— C19H22N2O3S
    2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)-N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)acetamide
    —— 2-[2-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)ethenyl]-1H-pyrimidin-6-one —— C14H11BrN2O2
    2-[2-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)ethenyl]-1H-pyrimidin-6-one
    —— N-[2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-thiophen-3-ylprop-2-enamide —— C19H22N2O2S
    N-[2-(2,3-dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethyl]-3-thiophen-3-ylprop-2-enamide
    —— N-[2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(furan-2-yl)prop-2-enamide —— C17H17NO4
    N-[2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]-3-(furan-2-yl)prop-2-enamide
    —— 3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H31ClN2O7
    3-[(4-chlorophenyl)methyl-(2-methylpropanoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(furan-2-ylmethyl)-amide —— C22H19NO8
    (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(furan-2-ylmethyl)-amide
    —— (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(furan-3-ylmethyl)-amide —— C22H19NO8
    (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(furan-3-ylmethyl)-amide
    —— 3-[acetyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C21H26N2O5
    3-[acetyl(cyclopropylmethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[acetyl(cyclohexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C25H34N2O7
    3-[acetyl(cyclohexyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(thiophen-3-ylmethyl)-amide —— C22H19NO7S
    (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(thiophen-3-ylmethyl)-amide
    —— (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(thiophen-2-ylmethyl)-amide —— C22H19NO7S
    (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid(thiophen-2-ylmethyl)-amide
    —— 3-[2-(3-fluorophenyl)ethyl-octanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C31H39FN2O5
    3-[2-(3-fluorophenyl)ethyl-octanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclohexyl(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H36N2O7
    3-[cyclohexyl(3-methylbut-2-enoyl)amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid 3-chloro-benzylamide —— C24H20ClNO7
    (S)-8-Acetyl-6,9-dihydroxy-3-methoxy-6b-methyl-1,7-dioxo-6b,7-dihydro-1H-4,11-dioxa-2-aza-benzo[a]fluorene-2-carboxylic acid 3-chloro-benzylamide
    —— 3-[(4-fluorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C27H31FN2O7
    3-[(4-fluorophenyl)methyl-propanoylamino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 2-Methyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-2,3-dihydro-1-benzofuran —— C19H20O2
    2-Methyl-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-2,3-dihydro-1-benzofuran
    —— 3-[furan-3-ylmethyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C23H26N2O6
    3-[furan-3-ylmethyl(propanoyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(4-fluorophenyl)methyl-pent-2-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H31FN2O7
    3-[(4-fluorophenyl)methyl-pent-2-enoylamino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[cyclopentanecarbonyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H41N3O8
    3-[cyclopentanecarbonyl(2-morpholin-4-ylethyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 4-hydroxy-N-(2-hydroxyethyl)-3-[2-morpholin-4-ylethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H35N3O6
    4-hydroxy-N-(2-hydroxyethyl)-3-[2-morpholin-4-ylethyl(pent-2-enoyl)amino]-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 1-Methyl-2-(2,3,6,7-tetrahydro-benzo[1,2-b;4,5-b'']difuran-4-yl)-ethyl-ammonium; chloride —— C13H18NO2+
    1-Methyl-2-(2,3,6,7-tetrahydro-benzo[1,2-b;4,5-b'']difuran-4-yl)-ethyl-ammonium; chloride
    —— [(2S)-1-[4-(trifluoromethyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl]propan-2-yl]azanium —— C14H17F3NO2+
    [(2S)-1-[4-(trifluoromethyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl]propan-2-yl]azanium
    —— 1-Methyl-2-(8-trifluoromethyl-2,3,6,7-tetrahydro-benzo[1,2-b;4,5-b'']difuran-4-yl)-ethyl-ammonium; chloride —— C14H17F3NO2+
    1-Methyl-2-(8-trifluoromethyl-2,3,6,7-tetrahydro-benzo[1,2-b;4,5-b'']difuran-4-yl)-ethyl-ammonium; chloride
    —— [(2R)-1-(2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)propan-2-yl]azanium —— C13H18NO2+
    [(2R)-1-(2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)propan-2-yl]azanium
    —— 3-[cyclobutanecarbonyl-[(4-methylphenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C30H34N2O7
    3-[cyclobutanecarbonyl-[(4-methylphenyl)methyl]amino]-8-formyl-4-hydroxy-N-(2-hydroxyethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[benzyl-(2-ethoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C26H30N2O6
    3-[benzyl-(2-ethoxyacetyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— 3-[(2-ethoxyacetyl)-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C29H36N2O8
    3-[(2-ethoxyacetyl)-[(4-methylphenyl)methyl]amino]-4-hydroxy-N-(2-hydroxyethyl)-8-(hydroxymethyl)-6-methoxy-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide
    —— methyl (3R)-3-(aminomethyl)-2,3-dihydro-1-benzofuran-7-carboxylate —— C11H13NO3
    methyl (3R)-3-(aminomethyl)-2,3-dihydro-1-benzofuran-7-carboxylate
    —— methyl (3R)-3-(aminomethyl)-2,3-dihydro-1-benzofuran-7-carboxylate;hydrochloride —— C11H14ClNO3
    methyl (3R)-3-(aminomethyl)-2,3-dihydro-1-benzofuran-7-carboxylate;hydrochloride
    —— 3-[cycloheptyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide —— C28H38N2O5
    3-[cycloheptyl(cyclopentanecarbonyl)amino]-4-hydroxy-N-(2-hydroxyethyl)-3,4,4a,9b-tetrahydrodibenzofuran-1-carboxamide