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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
    —— 7-[N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyloxy]-2,2-dimethyl-2,3-dihydrobenzofuran 66997-56-6 C19H27NO4S
    7-[N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyloxy]-2,2-dimethyl-2,3-dihydrobenzofuran
    —— Trihydroxy-2,4',4'-diphenylessigsaeurelacton 31542-79-7 C14H10O4
    Trihydroxy-2,4',4'-diphenylessigsaeurelacton
    —— 5a,10b-Bis(4-bromophenyl)-[1]benzofuro[2,3-b][1]benzofuran-3,8-diol 1224839-33-1 C26H16Br2O4
    5a,10b-Bis(4-bromophenyl)-[1]benzofuro[2,3-b][1]benzofuran-3,8-diol
    —— 2,2-dimethyl-2,3-dihydrobenzofuran-6-amine 31010-95-4 C10H13NO
    2,2-dimethyl-2,3-dihydrobenzofuran-6-amine
    —— 7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan 124435-71-8 C14H20O
    7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan
    —— 5-(2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5-yl)cyclohexane-1,3-dione 157189-02-1 C19H24O3
    5-(2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5-yl)cyclohexane-1,3-dione
    —— 6-fluoro-2,3-dihydro-benzofuran-2-carboxylic acid 26018-67-7 C9H7FO3
    6-fluoro-2,3-dihydro-benzofuran-2-carboxylic acid
    —— 7-tert-butyl-2,3-dihydro-3-ethyl-3-methylbenzofuran 205241-90-3 C15H22O
    7-tert-butyl-2,3-dihydro-3-ethyl-3-methylbenzofuran
    —— 5-Benzofuranmethanamine, 7-chloro-2,3-dihydro-N,2-dimethyl- 1550873-40-9 C11H14ClNO
    5-Benzofuranmethanamine, 7-chloro-2,3-dihydro-N,2-dimethyl-
    —— (2,2-dimethyl-2,3-dihydro-benzofuran-5-yl)-acetonitrile 57899-20-4 C12H13NO
    (2,2-dimethyl-2,3-dihydro-benzofuran-5-yl)-acetonitrile
    —— 5-methoxy-2,3-dihydrobenzofuran 13391-30-5 C9H10O2
    5-methoxy-2,3-dihydrobenzofuran
    —— 2,3-dihydro-7-methoxy-2,2-dimethyl-5-benzofurancarboxaldehyde 363185-19-7 C12H14O3
    2,3-dihydro-7-methoxy-2,2-dimethyl-5-benzofurancarboxaldehyde
    —— diethyl 2,2'-((1R,4S,4aR,9bS)-4-((tert-butyldimethylsilyl)oxy)-6-methoxy-1,4,4a,9b-tetrahydrodibenzo[b,d]furan-1,9b-diyl)diacetate 1440947-65-8 C27H40O7Si
    diethyl 2,2'-((1R,4S,4aR,9bS)-4-((tert-butyldimethylsilyl)oxy)-6-methoxy-1,4,4a,9b-tetrahydrodibenzo[b,d]furan-1,9b-diyl)diacetate
    —— tert-butyl 2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-(tert-butyldimethyl-silyloxy)-4-methoxy-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl(methyl)-carbamate 1315613-97-8 C31H49NO7Si
    tert-butyl 2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-(tert-butyldimethyl-silyloxy)-4-methoxy-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl(methyl)-carbamate
    —— (4S,4aS,9bR)-9-((1,3-dioxolan-2-yl)methyl)-6-methoxy-9b-(2-(methylamino)ethyl)-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-4-ol 1315614-04-0 C20H27NO5
    (4S,4aS,9bR)-9-((1,3-dioxolan-2-yl)methyl)-6-methoxy-9b-(2-(methylamino)ethyl)-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-4-ol
    —— 2,3-dihydro-3,3-dimethyl-7-methoxybenzofuran-4-carboxaldehyde 109433-14-9 C12H14O3
    2,3-dihydro-3,3-dimethyl-7-methoxybenzofuran-4-carboxaldehyde
    —— 5-Fluoro-3-methyl-2,3-dihydro-1-benzofuran 1428773-50-5 C9H9FO
    5-Fluoro-3-methyl-2,3-dihydro-1-benzofuran
    —— 3-(2,3-dihydro-7-methoxybenzo<b>furan-3-yl)propionic acid 155897-02-2 C12H14O4
    3-(2,3-dihydro-7-methoxybenzo<b>furan-3-yl)propionic acid
    —— 2-hydroxy-2,3-dihydro-1-benzofuran-4-carboxylic acid 1151738-95-2 C9H8O4
    2-hydroxy-2,3-dihydro-1-benzofuran-4-carboxylic acid
    —— 2-methoxy-2,3-dihydrobenzofuran-4-carboxylic acid methyl ester 1151739-02-4 C11H12O4
    2-methoxy-2,3-dihydrobenzofuran-4-carboxylic acid methyl ester
    —— 2-methoxy-2,3-dihydrobenzofuran-4-carboxylic acid 1151738-99-6 C10H10O4
    2-methoxy-2,3-dihydrobenzofuran-4-carboxylic acid
    —— 2-vinyl-2,3-dihydrobenzofuran 16198-39-3 C10H10O
    2-vinyl-2,3-dihydrobenzofuran
    —— 4aS,9aR-cis-4a-ethyl-6-methoxy-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridine R-(-)-mandelate 1182348-94-2 C8H8O3*C14H19NO2
    4aS,9aR-cis-4a-ethyl-6-methoxy-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridine R-(-)-mandelate
    —— (S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan 346696-58-0 C11H12O3
    (S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan
    —— 7-[5-formyl-2-trifluoromethoxy-phenyl]-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid dimethylamide 532440-89-4 C21H20F3NO4
    7-[5-formyl-2-trifluoromethoxy-phenyl]-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid dimethylamide
    —— ethyl 2,3-dihydro-4,6-bis(O-methoxymethyl)-2-<[tris(1-methylethyl)silyl]oxy>-3-benzofuranacetate 247570-77-0 C25H42O8Si
    ethyl 2,3-dihydro-4,6-bis(O-methoxymethyl)-2-<[tris(1-methylethyl)silyl]oxy>-3-benzofuranacetate
    —— 4,6-dihydroxy-3-phenyl-3-p-tolylbenzofuran-2(3H)-one 1373335-03-5 C21H16O4
    4,6-dihydroxy-3-phenyl-3-p-tolylbenzofuran-2(3H)-one
    —— (4,5,6-trimethoxy-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol 1240045-79-7 C14H20O5
    (4,5,6-trimethoxy-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol
    —— (2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)methanol 1240045-68-4 C14H20O2
    (2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)methanol
    —— (9aS)-8-Acetyl-1,7-dihydroxy-3-methoxy-N-(2-methoxybenzyl)-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide 925439-32-3 C25H23NO8
    (9aS)-8-Acetyl-1,7-dihydroxy-3-methoxy-N-(2-methoxybenzyl)-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide
    —— 5-hydroxy-3-phenyl-3-p-tolylbenzofuran-2(3H)-one 1373334-97-4 C21H16O3
    5-hydroxy-3-phenyl-3-p-tolylbenzofuran-2(3H)-one
    —— 2-tert-butyl-peroxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate 26244-32-6 C15H22O6S
    2-tert-butyl-peroxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate
    —— (1S,2S,7R,9S)-12-(chloromethyl)-5-methyl-4,6,10-trioxatetracyclo[7.7.0.02,7.011,16]hexadeca-11,13,15-triene 88277-16-1 C15H17ClO3
    (1S,2S,7R,9S)-12-(chloromethyl)-5-methyl-4,6,10-trioxatetracyclo[7.7.0.02,7.011,16]hexadeca-11,13,15-triene
    —— 5-bromo-6-nitro-2,3-dihydrobenzo[b]furan 84594-79-6 C8H6BrNO3
    5-bromo-6-nitro-2,3-dihydrobenzo[b]furan
    —— methyl {(3S)-6-[{7-[(2-amino-4-methylphenyl)amino]-2,3-dihydro-1-benzofuran-3-yl}(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate 1258399-65-3 C28H26F3N3O5
    methyl {(3S)-6-[{7-[(2-amino-4-methylphenyl)amino]-2,3-dihydro-1-benzofuran-3-yl}(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate
    —— 3-azido-5-chloro-4-fluoro-2,3-dihydro-1-benzofuran 1294003-38-5 C8H5ClFN3O
    3-azido-5-chloro-4-fluoro-2,3-dihydro-1-benzofuran
    —— (5R)-5-(5-(6-chloro-2,3-dihydrobenzofuran-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione 1400683-19-3 C22H22ClF3N2O2S
    (5R)-5-(5-(6-chloro-2,3-dihydrobenzofuran-3-ylamino)-2-fluorophenyl)-6,6-difluoro-5,7,7-trimethyl-1,4-oxazepane-3-thione
    —— 5-chloro-2,2,4,6-tetramethyl-7-nitro-2,3-dihydrobenzofuran 144983-32-4 C12H14ClNO3
    5-chloro-2,2,4,6-tetramethyl-7-nitro-2,3-dihydrobenzofuran
    —— 5-amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan 178322-43-5 C14H21NO
    5-amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan
    —— 2,8,13,19-Tetrakis(1,1-dimethylethyl)-11H,22H-4,6:6,10:15,17:17,21-tetramethanodibenzo<b,k><1,10>dioxacyclooctadecin-23,25-dione 145986-91-0 C44H52O4
    2,8,13,19-Tetrakis(1,1-dimethylethyl)-11H,22H-4,6:6,10:15,17:17,21-tetramethanodibenzo<b,k><1,10>dioxacyclooctadecin-23,25-dione
    —— 5-(allyloxy)-2,3-dihydro-2-(2-phenylethyl)benzofuran 138854-09-8 C19H20O2
    5-(allyloxy)-2,3-dihydro-2-(2-phenylethyl)benzofuran
    —— 3-[2-(2-Phenylethyl)-5-phenylmethoxy-2,3-dihydro-1-benzofuran-6-yl]propan-1-ol 139201-47-1 C26H28O3
    3-[2-(2-Phenylethyl)-5-phenylmethoxy-2,3-dihydro-1-benzofuran-6-yl]propan-1-ol
    —— 2,3-dihydro-5-methoxy-2-(2-phenylethyl)benzofuran 138854-08-7 C17H18O2
    2,3-dihydro-5-methoxy-2-(2-phenylethyl)benzofuran
    —— 5-(benzyloxy)-6-(3-bromopropyl)-2,3-dihydro-2-(2-phenylethyl)benzofuran 138854-18-9 C26H27BrO2
    5-(benzyloxy)-6-(3-bromopropyl)-2,3-dihydro-2-(2-phenylethyl)benzofuran
    —— 5-(benzyloxy)-2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)benzofuran 138854-30-5 C32H32O3
    5-(benzyloxy)-2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)benzofuran
    —— 2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-4-propyl-5-benzofuranol 139201-55-1 C28H32O3
    2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-4-propyl-5-benzofuranol
    —— 2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-5-benzofuranol 133174-26-2 C25H26O3
    2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-5-benzofuranol
    —— 6-allyl-2,3-dihydro-2-(2-phenylethyl)-5-benzofuranol 138853-84-6 C19H20O2
    6-allyl-2,3-dihydro-2-(2-phenylethyl)-5-benzofuranol
    —— 2,3-dihydro-2-(2-phenylethyl)-5-benzofuranol 133174-25-1 C16H16O2
    2,3-dihydro-2-(2-phenylethyl)-5-benzofuranol
    —— ethyl 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate 62717-20-8 C11H10Cl2O3
    ethyl 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate