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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
    —— (E/Z)-6-benzyloxy-2,3-dihydrobenzofuran-3-oxime O-benzyl ether 188884-82-4 C22H19NO3
    (E/Z)-6-benzyloxy-2,3-dihydrobenzofuran-3-oxime O-benzyl ether
    —— methyl 4-(2,3-dihydrobenzofuran-3-yl)-2-methylenebutanoate 1361133-02-9 C14H16O3
    methyl 4-(2,3-dihydrobenzofuran-3-yl)-2-methylenebutanoate
    —— ((3R)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)acetic acid 1452478-14-6 C17H14Cl2O4
    ((3R)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)acetic acid
    —— 2,2-dimethyl-N-(4-oxy-7-vinyl-2,3-dihydrofuro[3,2-b]pyridin-5-yl)butyramide 1029128-37-7 C15H20N2O3
    2,2-dimethyl-N-(4-oxy-7-vinyl-2,3-dihydrofuro[3,2-b]pyridin-5-yl)butyramide
    —— tert-butyl 2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,7,9a tetrahydrodibenzo[b,d]furan-9a-yl)ethyl(methyl)carbamate 1315613-99-0 C25H35NO7
    tert-butyl 2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,7,9a tetrahydrodibenzo[b,d]furan-9a-yl)ethyl(methyl)carbamate
    —— 2-Hydroxy-1,4-dimethyl-3-hexamethylenamino-5a,6,7,8,9,10-hexahydro-azepino<2.1-b>benzoxazol 18735-59-6 C20H30N2O2
    2-Hydroxy-1,4-dimethyl-3-hexamethylenamino-5a,6,7,8,9,10-hexahydro-azepino<2.1-b>benzoxazol
    —— 1422044-89-0 C21H20O5
    —— methyl 2,3-dihydro-5-hydroxy-2-methylbenzofuran-4-carboxylate 79952-89-9 C11H12O4
    methyl 2,3-dihydro-5-hydroxy-2-methylbenzofuran-4-carboxylate
    —— opt.-akt. 2-(2,3-Dihydro-2-benzofuryl)-2-propanol 24007-50-9 C11H14O2
    opt.-akt. 2-(2,3-Dihydro-2-benzofuryl)-2-propanol
    —— (E)-2-(2,2-bis(methoxymethyl)-7-trifluoromethylchroman-4-ylidene)acetic acid 1042973-49-8 C16H17F3O5
    (E)-2-(2,2-bis(methoxymethyl)-7-trifluoromethylchroman-4-ylidene)acetic acid
    —— 3-bromo-6,8-dichloro-3-nitro-2-trichloromethylchroman-4-ol 1283597-81-8 C10H5BrCl5NO4
    3-bromo-6,8-dichloro-3-nitro-2-trichloromethylchroman-4-ol
    —— ethyl 7-[2,3-dihydro-2,2,4-trimethyl-6-(propan-2-yl)benzo[b]furan-7-yl]-3,5-dihydroxyheptanoate 149245-40-9 C23H36O5
    ethyl 7-[2,3-dihydro-2,2,4-trimethyl-6-(propan-2-yl)benzo[b]furan-7-yl]-3,5-dihydroxyheptanoate
    —— N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methylacetamide 1315614-11-9 C22H27NO6
    N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methylacetamide
    —— ethyl (E)-7-chloro-2,3-dihydro-5-(o-fluorobenzoyl)-6-hydroxybenzofuran-2-carboxylate oxime 90246-88-1 C18H15ClFNO5
    ethyl (E)-7-chloro-2,3-dihydro-5-(o-fluorobenzoyl)-6-hydroxybenzofuran-2-carboxylate oxime
    —— 3-morpholin-4-yl-3-phenyl-3H-benzofuran-2-one 95218-96-5 C18H17NO3
    3-morpholin-4-yl-3-phenyl-3H-benzofuran-2-one
    —— 2-benzyl-2-methyl-2,3-dihydro-benzofuran 72374-38-0 C16H16O
    2-benzyl-2-methyl-2,3-dihydro-benzofuran
    —— ethyl (E)-7-chloro-2,3-dihydro-6-hydroxy-5-(α-thienylcarbonyl)benzofuran-2-carboxylate oxime 90246-92-7 C16H14ClNO5S
    ethyl (E)-7-chloro-2,3-dihydro-6-hydroxy-5-(α-thienylcarbonyl)benzofuran-2-carboxylate oxime
    —— (R)-5-Methoxycarbonylamino-2,3-dihydro-benzofuran-2-carboxylic acid 871213-69-3 C11H11NO5
    (R)-5-Methoxycarbonylamino-2,3-dihydro-benzofuran-2-carboxylic acid
    —— trans-10-Bromo-7-methoxy-4-methyl-1,3,4,4a,5,10b-hexahydro-2H-<1>benzopyrano<3,4-b>pyridine 118715-89-2 C14H18BrNO2
    trans-10-Bromo-7-methoxy-4-methyl-1,3,4,4a,5,10b-hexahydro-2H-<1>benzopyrano<3,4-b>pyridine
    —— 3,8-Dibrom-4b,9b-dimethyl-4b,9b-dihydro-benzofuro<3,2-b>benzofuran 4200-11-7 C16H12Br2O2
    3,8-Dibrom-4b,9b-dimethyl-4b,9b-dihydro-benzofuro<3,2-b>benzofuran
    —— 1,6-Dimethoxy-4b,9b-dimethyl-4b,9b-dihydro-benzofuro<3,2-b>benzofuran 4200-08-2 C18H18O4
    1,6-Dimethoxy-4b,9b-dimethyl-4b,9b-dihydro-benzofuro<3,2-b>benzofuran
    —— N-(2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methylacetamide 1315614-10-8 C22H29NO6
    N-(2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methylacetamide
    —— 1422044-90-3 C22H22O6
    —— 6-chloro-2H-spiro[benzofuran-3,1'-cyclohexan]-2-one 1419174-54-1 C13H13ClO2
    6-chloro-2H-spiro[benzofuran-3,1'-cyclohexan]-2-one
    —— methyl (2-hydroxymethyl-2,3-dihydrobenzo[b]furan-5-yl)acetate 129503-79-3 C12H14O4
    methyl (2-hydroxymethyl-2,3-dihydrobenzo[b]furan-5-yl)acetate
    —— 6-methyl-benzofuran-3-one oxime 90563-73-8 C9H9NO2
    6-methyl-benzofuran-3-one oxime
    —— 3-{6-[(2,6-dichloro-4-methylphenyl)methoxy]-7-fluoro-2H-spiro[l-benzofuran-3,4'-piperidine]-1'-yl}propanoic acid hydrochloride 1355085-22-1 C23H24Cl2FNO4*ClH
    3-{6-[(2,6-dichloro-4-methylphenyl)methoxy]-7-fluoro-2H-spiro[l-benzofuran-3,4'-piperidine]-1'-yl}propanoic acid hydrochloride
    —— 2-Isopropylamino-1-(2-methyl-2,3-dihydro-benzofuran-5-yl)-ethanol 6992-88-7 C14H21NO2
    2-Isopropylamino-1-(2-methyl-2,3-dihydro-benzofuran-5-yl)-ethanol
    —— 4-(5-bromo-4-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine 1619243-86-5 C13H15BrFNO
    4-(5-bromo-4-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine
    —— 2-acetyl-3<i>t</i>-hydroxymethyl-1-methyl-(3a<i>r</i>,9b<i>c</i>)-1,2,3,3a,4,9b-hexahydro-chromeno[4,3-<i>c</i>]pyrazole 25614-44-2 C14H18N2O3
    2-acetyl-3<i>t</i>-hydroxymethyl-1-methyl-(3a<i>r</i>,9b<i>c</i>)-1,2,3,3a,4,9b-hexahydro-chromeno[4,3-<i>c</i>]pyrazole
    —— 5-fluoro-2-iodomethyl-2,3-dihydro-benzofuran 135634-29-6 C9H8FIO
    5-fluoro-2-iodomethyl-2,3-dihydro-benzofuran
    —— (S)-2-((R)-5-Ethyl-2,3-dihydro-benzofuran-2-yl)-propan-1-ol 87503-39-7 C13H18O2
    (S)-2-((R)-5-Ethyl-2,3-dihydro-benzofuran-2-yl)-propan-1-ol
    —— methyl {(3S)-6-[(3-bromo-2,4-dimethylbenzyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate 1258398-79-6 C20H22BrNO3
    methyl {(3S)-6-[(3-bromo-2,4-dimethylbenzyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate
    —— (2R,3R)-3-Hydroxy-2-methoxy-5-methyl-2,3-dihydro-benzofuran-2,3-dicarboxylic acid dimethyl ester 73499-90-8 C14H16O7
    (2R,3R)-3-Hydroxy-2-methoxy-5-methyl-2,3-dihydro-benzofuran-2,3-dicarboxylic acid dimethyl ester
    —— 7-Methoxy-2,3-dihydro-benzofuran-2-carbonitrile 185407-86-7 C10H9NO2
    7-Methoxy-2,3-dihydro-benzofuran-2-carbonitrile
    —— (2R)-14-(4-fluorophenyl)-N,2-dimethyl-9-methylsulfonyl-13-oxa-3,4,5,9-tetrazatetracyclo[8.7.0.03,7.012,16]heptadeca-1(10),4,6,11,14,16-hexaene-15-carboxamide 1374230-36-0 C22H20FN5O4S
    (2R)-14-(4-fluorophenyl)-N,2-dimethyl-9-methylsulfonyl-13-oxa-3,4,5,9-tetrazatetracyclo[8.7.0.03,7.012,16]heptadeca-1(10),4,6,11,14,16-hexaene-15-carboxamide
    —— ethyl 7-[2,3-dihydro-2,2,4,6-tetramethylbenzo[b]furan-7-yl]-3,5-dihydroxyheptanoate 149245-12-5 C21H32O5
    ethyl 7-[2,3-dihydro-2,2,4,6-tetramethylbenzo[b]furan-7-yl]-3,5-dihydroxyheptanoate
    —— 2,3-dihydro-3,3-dimethyl-2-hydroxy-6-isopropylbenzofuran-5-yl methanesulphonate 26225-77-4 C14H20O5S
    2,3-dihydro-3,3-dimethyl-2-hydroxy-6-isopropylbenzofuran-5-yl methanesulphonate
    —— (3S,4aR,6aS,12aR,12bS)-3,11-diacetoxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene 479637-03-1 C25H34O5
    (3S,4aR,6aS,12aR,12bS)-3,11-diacetoxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene
    —— 2,3-dihydro-3,3-dimethyl-2-hydroxy-6-methoxybenzofuran-5-yl methanesulphonate 26322-83-8 C12H16O6S
    2,3-dihydro-3,3-dimethyl-2-hydroxy-6-methoxybenzofuran-5-yl methanesulphonate
    —— trans-2-Morpholino-3-brom-chroman 36055-15-9 C13H16BrNO2
    trans-2-Morpholino-3-brom-chroman
    —— ethyl 2-bromo-3-oxo-3-(7-bromo-3-phenyl-2,3-dihydrobenzofuran-3-yl)-propanoate 918304-97-9 C19H16Br2O4
    ethyl 2-bromo-3-oxo-3-(7-bromo-3-phenyl-2,3-dihydrobenzofuran-3-yl)-propanoate
    —— 6-[2-(2-amino-1H-imidazol-5-yl)ethylamino]-1-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-[(4-ethylphenyl)methyl]-1,3,5-triazine-2,4-dione 1148128-10-2 C26H29N7O3
    6-[2-(2-amino-1H-imidazol-5-yl)ethylamino]-1-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-[(4-ethylphenyl)methyl]-1,3,5-triazine-2,4-dione
    —— 892406-68-7 C20H35NO4Si
    —— 3-Benzofurancarboxamide,7-bromo-2,3-dihydro-3-phenyl-N-[(1S)-1-phenylethyl]-, (3S)- 217493-13-5 C23H20BrNO2
    3-Benzofurancarboxamide,7-bromo-2,3-dihydro-3-phenyl-N-[(1S)-1-phenylethyl]-, (3S)-
    —— 2-ethyl-5,8-dimethyl-2H-chromen-7-ol 1609940-30-8 C13H16O2
    2-ethyl-5,8-dimethyl-2H-chromen-7-ol
    —— (1-Benzofuran-3-ylideneamino) acetate 1041684-08-5 C10H9NO3
    (1-Benzofuran-3-ylideneamino) acetate
    —— 1432752-91-4 C13H16O3
    —— 3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl acetate 1380697-52-8 C12H14O3
    3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl acetate
    —— (+/-)-2,3,4,5,6,6a-Hexahydro-3-formyl-8-methoxy-11-chloro-1H-4,11b-methanobenzofuro<3,2-d>azocin-6-one 88304-36-3 C16H16ClNO4
    (+/-)-2,3,4,5,6,6a-Hexahydro-3-formyl-8-methoxy-11-chloro-1H-4,11b-methanobenzofuro<3,2-d>azocin-6-one