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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
    —— (2R,3R)-3-Hydroxy-2-methoxy-5,7-dimethyl-2,3-dihydro-benzofuran-2,3-dicarboxylic acid dimethyl ester 73499-91-9 C15H18O7
    (2R,3R)-3-Hydroxy-2-methoxy-5,7-dimethyl-2,3-dihydro-benzofuran-2,3-dicarboxylic acid dimethyl ester
    —— 5-butyl-6,8-diethoxy-2,3,4-trimethyl-2,3,4,5-tetrahydro-benzo[<i>f</i>][1,4]oxazepine 47334-26-9 C20H33NO3
    5-butyl-6,8-diethoxy-2,3,4-trimethyl-2,3,4,5-tetrahydro-benzo[<i>f</i>][1,4]oxazepine
    —— 3-[2,3-dihydro-2,2,6-trimethyl-4-(propan-2-yl)benzo[b]furan-7-yl]propanol 149245-37-4 C17H26O2
    3-[2,3-dihydro-2,2,6-trimethyl-4-(propan-2-yl)benzo[b]furan-7-yl]propanol
    —— 2-(3-methyl-2H-1-benzofuran-3-yl)-N-phenylmethoxyacetamide 252857-05-9 C18H19NO3
    2-(3-methyl-2H-1-benzofuran-3-yl)-N-phenylmethoxyacetamide
    —— 7-Methoxy-3-[1-(5-nitro-furan-2-yl)-meth-(Z)-ylidene]-isothiochroman-4-one 24417-41-2 C15H11NO5S
    7-Methoxy-3-[1-(5-nitro-furan-2-yl)-meth-(Z)-ylidene]-isothiochroman-4-one
    —— 6-((2,4-dichlorobenzyl)oxy)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-3-carboxylic acid 1452478-30-6 C17H14Cl2O5
    6-((2,4-dichlorobenzyl)oxy)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-3-carboxylic acid
    —— 3-[5-amino-2,3-dihydro-2,2,4,6-tetramethylbenzo[b]furan-7-yl]propanol 149245-52-3 C15H23NO2
    3-[5-amino-2,3-dihydro-2,2,4,6-tetramethylbenzo[b]furan-7-yl]propanol
    —— 2,3-Dihydro-2,3-dihydroxy-benzo<b>furan-2,3-dicarbonsaeure-methylester 342817-56-5 C12H12O7
    2,3-Dihydro-2,3-dihydroxy-benzo<b>furan-2,3-dicarbonsaeure-methylester
    —— 3-(2-chloro-benzyl)-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester 936564-16-8 C17H15ClO3
    3-(2-chloro-benzyl)-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester
    —— [(4S)-4-[(E)-3-(4-chlorophenyl)prop-2-enyl]-4-methylchromen-3-yl] 2,2-dimethylpropanoate 1134203-05-6 C24H25ClO3
    [(4S)-4-[(E)-3-(4-chlorophenyl)prop-2-enyl]-4-methylchromen-3-yl] 2,2-dimethylpropanoate
    —— (S)-3-acetyloxy-2,2-dimethyl-5-methoxymethoxybenzo[b]pyran-7-methanal 611179-97-6 C16H20O6
    (S)-3-acetyloxy-2,2-dimethyl-5-methoxymethoxybenzo[b]pyran-7-methanal
    —— (R)-1-(2,3-dihydrobenzofuran-5-yl)prop-2-en-1-ol 1282033-72-0 C11H12O2
    (R)-1-(2,3-dihydrobenzofuran-5-yl)prop-2-en-1-ol
    —— 2-Aminomethyl-2,3,7,8-tetrahydro-5,8,8-trimethyl-6H-furo[2,3-e]indol-7-thione·hydrochloride 170684-46-5 C14H18N2OS*ClH
    2-Aminomethyl-2,3,7,8-tetrahydro-5,8,8-trimethyl-6H-furo[2,3-e]indol-7-thione·hydrochloride
    —— trans-2-nitro-3-hydroxy-4,6-dimethoxy-2,3-dihydrobenzo<b>furan 96089-37-1 C10H11NO6
    trans-2-nitro-3-hydroxy-4,6-dimethoxy-2,3-dihydrobenzo<b>furan
    —— (-)-5-Acetoxy-2-octyl-2,3-dihydrobenzofuran 189032-98-2 C18H26O3
    (-)-5-Acetoxy-2-octyl-2,3-dihydrobenzofuran
    —— (S)-2-[6-(allyloxy)-2,3-dihydrobenzofuran-2-yl]propan-2-yl acetate 1144506-98-8 C16H20O4
    (S)-2-[6-(allyloxy)-2,3-dihydrobenzofuran-2-yl]propan-2-yl acetate
    —— 2,3-dihydro-3,3-dipropylbenzofuran 204266-15-9 C14H20O
    2,3-dihydro-3,3-dipropylbenzofuran
    —— 5-Formyl-6,7-dihydroxy-cumaran 10338-28-0 C9H8O4
    5-Formyl-6,7-dihydroxy-cumaran
    —— tert-butyl 2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,9,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl(methyl)carbamate 1315614-00-6 C25H35NO7
    tert-butyl 2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,9,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl(methyl)carbamate
    —— (5-bromo-2,3-dihydro-1-benzofuran-7-yl)amine hydrochloride 1287795-17-8 C8H8BrNO*ClH
    (5-bromo-2,3-dihydro-1-benzofuran-7-yl)amine hydrochloride
    —— 3-deuteriomethyl-5-methyl-7-trimethylsilyl-2,3-dihydrobenzofuran 869085-42-7 C13H20OSi
    3-deuteriomethyl-5-methyl-7-trimethylsilyl-2,3-dihydrobenzofuran
    —— 14-Brom-16-piperidinomethylsiccanin 36870-98-1 C28H40BrNO3
    14-Brom-16-piperidinomethylsiccanin
    —— 3-(3-hydroxy-2-methyl-3H-1-benzofuran-2-yl)propanenitrile 1159585-80-4 C12H13NO2
    3-(3-hydroxy-2-methyl-3H-1-benzofuran-2-yl)propanenitrile
    —— 5-(2-Nitroethenyl)-2,3-dihydro-1-benzofuran 874782-01-1 C10H9NO3
    5-(2-Nitroethenyl)-2,3-dihydro-1-benzofuran
    —— ethyl (2R,3S)-3-hydroxy-5-methoxy-3-methyl-2H-1-benzofuran-2-carboxylate 142143-40-6 C13H16O5
    ethyl (2R,3S)-3-hydroxy-5-methoxy-3-methyl-2H-1-benzofuran-2-carboxylate
    —— ethyl (E)-5-(1-(acetoxyimino)-3-methylbutyl)-7-chloro-6-hydroxy-2,3-dihydrobenzofuran-2-carboxylate 95635-15-7 C18H22ClNO6
    ethyl (E)-5-(1-(acetoxyimino)-3-methylbutyl)-7-chloro-6-hydroxy-2,3-dihydrobenzofuran-2-carboxylate
    —— 6-Fluoro-2-methyl-2,3-dihydro-1-benzofuran-3-amine hydrochloride 1803587-48-5 C9H11ClFNO
    6-Fluoro-2-methyl-2,3-dihydro-1-benzofuran-3-amine hydrochloride
    —— ethyl 7-[2,3-dihydro-2,2,4,6-tetramethyl-5-dimethylaminobenzo[b]furan-7-yl]-3,5-dihydroxyheptanoate 149245-56-7 C23H37NO5
    ethyl 7-[2,3-dihydro-2,2,4,6-tetramethyl-5-dimethylaminobenzo[b]furan-7-yl]-3,5-dihydroxyheptanoate
    —— 2-(2-amino-1H-imidazol-1-yl)-N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-acetamide trifluoroacetate 1048960-35-5 C2HF3O2*C22H31N5O2
    2-(2-amino-1H-imidazol-1-yl)-N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-acetamide trifluoroacetate
    —— 2-(2'-methoxyethoxy)-2,3-dihydro-3-methylenebenzofuran 1187956-35-9 C12H14O3
    2-(2'-methoxyethoxy)-2,3-dihydro-3-methylenebenzofuran
    —— 2,3,3a,8a-Tetrahydro-6-hydroxy-4-methoxy-2-oxo-furo<2,3-b>benzofuran 18022-42-9 C11H10O5
    2,3,3a,8a-Tetrahydro-6-hydroxy-4-methoxy-2-oxo-furo<2,3-b>benzofuran
    —— 5-methoxy-3-methyl-2H-1-benzofuran-3-ol 88112-05-4 C10H12O3
    5-methoxy-3-methyl-2H-1-benzofuran-3-ol
    —— 2-Methoxy-2,3-dihydro-benzofuran-5-carboxylic acid methyl ester 121045-49-6 C11H12O4
    2-Methoxy-2,3-dihydro-benzofuran-5-carboxylic acid methyl ester
    —— 2-Hydroxy-4,4-diphenyl-chroman 19326-66-0 C21H18O2
    2-Hydroxy-4,4-diphenyl-chroman
    —— 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (diisobutylaminosulfenyl)(methyl)carbamate 55285-16-0 C20H32N2O3S
    2,3-dihydro-2,2-dimethyl-7-benzofuranyl (diisobutylaminosulfenyl)(methyl)carbamate
    —— bis-4,4'-(8-chloro-2,2-dimethylchromen) 80056-02-6 C22H20Cl2O2
    bis-4,4'-(8-chloro-2,2-dimethylchromen)
    —— (5-methyl-2,3-dihydro-benzofuran-7-yl)-acetyl chloride 121159-56-6 C11H11ClO2
    (5-methyl-2,3-dihydro-benzofuran-7-yl)-acetyl chloride
    —— 2-iodomethyl-4,6,7-trimethyl-3-phenyl-2,3-dihydrobenzofuran-5-yl acetate 216989-60-5 C20H21IO3
    2-iodomethyl-4,6,7-trimethyl-3-phenyl-2,3-dihydrobenzofuran-5-yl acetate
    —— 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-(2-pyridylsulfamoylcarbamoyl) N-methylcarbamate 129043-27-2 C18H20N4O6S
    2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-(2-pyridylsulfamoylcarbamoyl) N-methylcarbamate
    —— (E)-N-(2-benzyl-3,3-diethoxy-1-benzofuran-2-yl)-1-(4-methoxyphenyl)methanimine 130495-06-6 C27H29NO4
    (E)-N-(2-benzyl-3,3-diethoxy-1-benzofuran-2-yl)-1-(4-methoxyphenyl)methanimine
    —— 4-amino-2-(ethylsulfanylmethyl)phenolate;cobalt(2+) 89299-14-9 C18H24CoN2O2S2
    4-amino-2-(ethylsulfanylmethyl)phenolate;cobalt(2+)
    —— 2,3-trans-3,4-cis-3,4-O-isopropylidene-4'-methoxyflavan 107579-02-2 C19H20O4
    2,3-trans-3,4-cis-3,4-O-isopropylidene-4'-methoxyflavan
    —— 3-Methyl-4-(β-chlorpropionylamino)-chroman 18084-81-6 C13H16ClNO2
    3-Methyl-4-(β-chlorpropionylamino)-chroman
    —— 7-allyl-9-methoxy-3-methyl-6-(2-methyl-allyloxy)-2,3,4,5-tetrahydrobenzo[b]oxepine 1384833-28-6 C19H26O3
    7-allyl-9-methoxy-3-methyl-6-(2-methyl-allyloxy)-2,3,4,5-tetrahydrobenzo[b]oxepine
    —— 2',3',4',6',7',9',10',10a'-octahydro-1'H,3H-spiro[benzofuran-2,8'-pyrido[1,2-a]azepine]-5-carbaldehyde 1258431-32-1 C18H23NO2
    2',3',4',6',7',9',10',10a'-octahydro-1'H,3H-spiro[benzofuran-2,8'-pyrido[1,2-a]azepine]-5-carbaldehyde
    —— 6-((2,4-dichlorobenzyl)oxy)-N-methoxy-1-benzofuran-3(2H)-imine 1452479-69-4 C16H13Cl2NO3
    6-((2,4-dichlorobenzyl)oxy)-N-methoxy-1-benzofuran-3(2H)-imine
    —— (3aS,8aS)-4-(tert-butyldimethylsilyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran-2-one 225917-69-1 C17H24O5Si
    (3aS,8aS)-4-(tert-butyldimethylsilyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran-2-one
    —— Methyl-carbamic acid (4-chloro-phenyl)-(5,6,7,8-tetrachloro-3-thiophen-2-yl-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methyl ester 73860-70-5 C21H14Cl5NO4S
    Methyl-carbamic acid (4-chloro-phenyl)-(5,6,7,8-tetrachloro-3-thiophen-2-yl-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methyl ester
    —— tert-butyl 1-cyano-5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylate 1236004-48-0 C18H21NO5
    tert-butyl 1-cyano-5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylate
    —— 7-chloro-2,3-dihydro-2-(hydroxymethyl)-5-nitro-6-(β-nitrovinyl)benzofuran 88062-20-8 C11H9ClN2O6
    7-chloro-2,3-dihydro-2-(hydroxymethyl)-5-nitro-6-(β-nitrovinyl)benzofuran