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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
    —— 1-(2,7-Dimethyl-2,3,7,8-tetrahydro-benzo[1,2-b;3,4-b']difuran-5-yl)-ethanone 117156-80-6 C14H16O3
    1-(2,7-Dimethyl-2,3,7,8-tetrahydro-benzo[1,2-b;3,4-b']difuran-5-yl)-ethanone
    —— ethyl 6-amino-2,3-dihydro-1-benzofuran-2-carboxylate 944447-80-7 C11H13NO3
    ethyl 6-amino-2,3-dihydro-1-benzofuran-2-carboxylate
    —— methyl 6-(methoxymethoxy)-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carboxylate 1612147-02-0 C15H18O5
    methyl 6-(methoxymethoxy)-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-carboxylate
    —— rac-(6R,7S,12R,13R)-13-hydroxy-13-methyl-6,7,12,13-tetrahydro-6,12-epoxydibenzo[b,f]oxonin-7-yl acetate 130413-20-6 C19H18O5
    rac-(6R,7S,12R,13R)-13-hydroxy-13-methyl-6,7,12,13-tetrahydro-6,12-epoxydibenzo[b,f]oxonin-7-yl acetate
    —— (2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one oxime 3276-14-0 C23H23NO6
    (2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one oxime
    —— 2-methoxy-N-methyl-5-(2-methyl-5-(5-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-f]pyrimidin-7-yl)benzenesulfonamide 883736-17-2 C21H23N7O3S
    2-methoxy-N-methyl-5-(2-methyl-5-(5-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-f]pyrimidin-7-yl)benzenesulfonamide
    —— N-(2-chloropyrimidin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)-2,3-dihydrobenzofuran-5-carboxamide 1224600-22-9 C19H20ClN3O3
    N-(2-chloropyrimidin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)-2,3-dihydrobenzofuran-5-carboxamide
    —— 7-bromo-5-hydroxy-4-nitro-2-(2-oxoethyl)-2,3-dihydrobenzo[b]furan ethylene acetal 197578-62-4 C12H12BrNO6
    7-bromo-5-hydroxy-4-nitro-2-(2-oxoethyl)-2,3-dihydrobenzo[b]furan ethylene acetal
    —— 15-oxopuupehenol 19,20-diacetate 851279-19-1 C25H32O6
    15-oxopuupehenol 19,20-diacetate
    —— 5-[(E)-3-Amino-3-(2-ethoxycarbonyl-propylsulfanyl)-acryloyl]-6,7-dichloro-2,3-dihydro-benzofuran-2-carboxylic acid tert-butyl ester 126201-04-5 C22H27Cl2NO6S
    5-[(E)-3-Amino-3-(2-ethoxycarbonyl-propylsulfanyl)-acryloyl]-6,7-dichloro-2,3-dihydro-benzofuran-2-carboxylic acid tert-butyl ester
    —— methyl [(3S)-6-{[(3S)-7-{[4-(methylsulfonyl)phenyl]amino}-2,3-dihydro-1-benzofuran-3-yl](trifluoroacetyl)amino}-2,3-dihydro-1-benzofuran-3-yl]acetate 1258402-14-0 C28H25F3N2O7S
    methyl [(3S)-6-{[(3S)-7-{[4-(methylsulfonyl)phenyl]amino}-2,3-dihydro-1-benzofuran-3-yl](trifluoroacetyl)amino}-2,3-dihydro-1-benzofuran-3-yl]acetate
    —— (+/-)-2-(azidomethyl)-5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran 852111-42-3 C13H10ClN3OS
    (+/-)-2-(azidomethyl)-5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran
    —— 3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan 820259-17-4 C22H22O
    3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan
    —— 3-(8-methoxy-2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-yl)propionic acid tert-butyl ester 920515-65-7 C18H24O5
    3-(8-methoxy-2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-yl)propionic acid tert-butyl ester
    —— 2,2,3,6,6,7-hexamethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-carbaldehyde 1313913-89-1 C17H22O3
    2,2,3,6,6,7-hexamethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-carbaldehyde
    —— 5-bromo-3-(4-isopropyl-2-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran 820259-15-2 C21H25BrO2
    5-bromo-3-(4-isopropyl-2-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran
    —— 2,3,4,5,5a,10b-Hexahydro-9,10b-dimethyl-1H-benzofuro<2,3-d>azepin 86658-30-2 C14H19NO
    2,3,4,5,5a,10b-Hexahydro-9,10b-dimethyl-1H-benzofuro<2,3-d>azepin
    —— N'-(2,2-Dimethyl-2,3-dihydro-benzofuran-7-yl)-hydrazinecarboxylic acid allyl ester 111268-79-2 C14H18N2O3
    N'-(2,2-Dimethyl-2,3-dihydro-benzofuran-7-yl)-hydrazinecarboxylic acid allyl ester
    —— 5-methyl-4-perhydropyran-2-yloxy-2,3-dihydrobenzo[b]furan 600176-60-1 C14H18O3
    5-methyl-4-perhydropyran-2-yloxy-2,3-dihydrobenzo[b]furan
    —— Methyl 4-((1S,2R,3aS,8bS)-2-((tert-butyldimethylsilyl)oxy)-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl)butanoate 1416129-68-4 C23H36O5Si
    Methyl 4-((1S,2R,3aS,8bS)-2-((tert-butyldimethylsilyl)oxy)-1-(hydroxymethyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl)butanoate
    —— 2.2.2'.2'-Tetramethyl-3.3'-bicumaran 111977-51-6 C20H22O2
    2.2.2'.2'-Tetramethyl-3.3'-bicumaran
    —— Ethyl 4-(3-methoxypropoxy)-2,3-dihydro-1-benzofuran-6-carboxylate 944141-32-6 C15H20O5
    Ethyl 4-(3-methoxypropoxy)-2,3-dihydro-1-benzofuran-6-carboxylate
    —— 2,3-dihydro-2,3-dimethyl-3-methoxybenzo<b>furan-2-ol 131588-89-1 C11H14O3
    2,3-dihydro-2,3-dimethyl-3-methoxybenzo<b>furan-2-ol
    —— 6,7-dichloro-2,3-dihydro-5-[(1-hydroxy-2-phenyl)-ethyl]benzofuran-2-carboxylic acid 67287-25-6 C17H14Cl2O4
    6,7-dichloro-2,3-dihydro-5-[(1-hydroxy-2-phenyl)-ethyl]benzofuran-2-carboxylic acid
    —— (3S,4R)-3-allyl-4-(nitromethyl)chroman-2-ol 1260789-29-4 C13H15NO4
    (3S,4R)-3-allyl-4-(nitromethyl)chroman-2-ol
    —— 3-ethyl-3-phenylbenzofuran-2(3H)-one 4374-69-0 C16H14O2
    3-ethyl-3-phenylbenzofuran-2(3H)-one
    —— ethyl 3-(5-(formylamino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)propanoate 1206733-86-9 C25H31NO4
    ethyl 3-(5-(formylamino)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)propanoate
    —— methyl (3Z)-3-[(dimethylamino)methylidene]-6-fluoro-4-oxo-3,4-dihydro-2H-chroman-2-carboxylate 1354560-75-0 C14H14FNO4
    methyl (3Z)-3-[(dimethylamino)methylidene]-6-fluoro-4-oxo-3,4-dihydro-2H-chroman-2-carboxylate
    —— O-Ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-5-nitro-7-benzofuranyl)thiophosphate 96408-32-1 C15H22NO6PS
    O-Ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-5-nitro-7-benzofuranyl)thiophosphate
    —— ethyl 5-iodo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate 1352740-13-6 C13H15IO3
    ethyl 5-iodo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate
    —— 1446282-64-9 C20H24N2O2
    —— 8-(2,4-dichlorophenyl)-6-(propylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine 488124-60-3 C20H21Cl2NOS
    8-(2,4-dichlorophenyl)-6-(propylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine
    —— 5-bromo-3-(4-isopropylphenyl)-3,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran 820257-32-7 C21H25BrO
    5-bromo-3-(4-isopropylphenyl)-3,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran
    —— methyl 4-bromo-2,3-dihydro-5-hydroxy-6-methyl-3-(phenoxycarbonyloxymethyl)benzofuran-2-carboxylate 84019-26-1 C19H17BrO7
    methyl 4-bromo-2,3-dihydro-5-hydroxy-6-methyl-3-(phenoxycarbonyloxymethyl)benzofuran-2-carboxylate
    —— (+/-)-8,9b-dimethyl-(4a<i>r</i>,9b<i>c</i>)-1,4,4a,9b-tetrahydro-2<i>H</i>-dibenzofuran-3-one semicarbazone 108170-26-9 C15H19N3O2
    (+/-)-8,9b-dimethyl-(4a<i>r</i>,9b<i>c</i>)-1,4,4a,9b-tetrahydro-2<i>H</i>-dibenzofuran-3-one semicarbazone
    —— (-)-(6S,6aR,10S,10aR)-ethyl 2,4-dichloro-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate 1631166-06-7 C17H17Cl2NO5
    (-)-(6S,6aR,10S,10aR)-ethyl 2,4-dichloro-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate
    —— 6-(5-Methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol 849354-11-6 C18H21F3O4S
    6-(5-Methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol
    —— 3,3-dimethyl-5-[(1S,2S)-1,2-methano-3-oxo-propyl]-2,3-dihydro-benzofuran 623176-69-2 C14H16O2
    3,3-dimethyl-5-[(1S,2S)-1,2-methano-3-oxo-propyl]-2,3-dihydro-benzofuran
    —— 2-(3-Diethylamino-propylaminomethyl)-2,3-dihydro-benzofuran 21130-32-5 C16H26N2O
    2-(3-Diethylamino-propylaminomethyl)-2,3-dihydro-benzofuran
    —— 2,3-dihydro-2,3,7-trimethyl-2,3-epoxybenzofuran 136795-94-3 C11H12O2
    2,3-dihydro-2,3,7-trimethyl-2,3-epoxybenzofuran
    —— 5-(tributylstannyl)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide 123266-60-4 C28H48N2O2Sn
    5-(tributylstannyl)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide
    —— (+/-)-4a,8-dimethyl-(4a<i>r</i>,9b<i>c</i>)-1,2,3,4,4a,9b-hexahydro-dibenzofuran-2ξ-ol 108124-57-8 C14H18O2
    (+/-)-4a,8-dimethyl-(4a<i>r</i>,9b<i>c</i>)-1,2,3,4,4a,9b-hexahydro-dibenzofuran-2ξ-ol
    —— N-benzyl-3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan-5-amine 820259-54-9 C29H29NO
    N-benzyl-3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan-5-amine
    —— 3-(4-bromophenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran 820259-00-5 C17H17BrO
    3-(4-bromophenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran
    —— 2-[2-(4-fluorophenyl)-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl]ethanamine hydrochloride 1031849-49-6 C17H16FN3O*ClH
    2-[2-(4-fluorophenyl)-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl]ethanamine hydrochloride
    —— Cyclopropanecarboxylic acid (7-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-amide 62035-40-9 C14H17NO3
    Cyclopropanecarboxylic acid (7-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-amide
    —— 65769-05-3 C20H22O4
    —— ethyl 4-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)-2-butenoate 154954-47-9 C18H24O4
    ethyl 4-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)-2-butenoate
    —— 3-(4-isopropylphenyl)-5-methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran 820257-93-0 C22H28O2
    3-(4-isopropylphenyl)-5-methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran
    —— 5-bromo-4,6,7-trimethyl-3-phenyl-2,3-dihydro-1-benzofuran 820259-03-8 C17H17BrO
    5-bromo-4,6,7-trimethyl-3-phenyl-2,3-dihydro-1-benzofuran