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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
    —— (R)-2-(1-hydroxy-1-methylethyl)-2,3-dihydro-benzofuran-6-ol 21491-60-1 C11H14O3
    (R)-2-(1-hydroxy-1-methylethyl)-2,3-dihydro-benzofuran-6-ol
    —— 5-(2-Cyclohexylmethyl-2,3-dihydro-benzofuran-5-ylmethyl)-thiazolidine-2,4-dione 109209-13-4 C19H23NO3S
    5-(2-Cyclohexylmethyl-2,3-dihydro-benzofuran-5-ylmethyl)-thiazolidine-2,4-dione
    —— 6,7-dichloro-2-ethoxymethyl-2,3-dihydrobenzofuran 103969-52-4 C11H12Cl2O2
    6,7-dichloro-2-ethoxymethyl-2,3-dihydrobenzofuran
    —— 1-(7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-3-thiabutan-1-one 177365-35-4 C17H24O2S
    1-(7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-3-thiabutan-1-one
    —— 2,3-dihydro-4,5,6-trimethylbenzo[b]furan 89240-12-0 C11H14O
    2,3-dihydro-4,5,6-trimethylbenzo[b]furan
    —— 5-bromo-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran 1243543-40-9 C13H17BrO
    5-bromo-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran
    —— (2S)-5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran 1243544-02-6 C12H15BrO
    (2S)-5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran
    —— (2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol 784163-67-3 C13H18O2
    (2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol
    —— (5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol 1243544-85-5 C13H17BrO2
    (5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol
    —— (S)-(2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl methanesulfonate 204065-21-4 C14H20O4S
    (S)-(2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl methanesulfonate
    —— (S)-2,3-dihydro-2,4,6,7-tetramethyl-2-benzofuranmethanol 204065-20-3 C13H18O2
    (S)-2,3-dihydro-2,4,6,7-tetramethyl-2-benzofuranmethanol
    —— 3-(1-Aza-bicyclo[2.2.2]oct-2-en-3-yl)-2,3-dihydro-benzofuran-3-ol 1027234-62-3 C15H17NO2
    3-(1-Aza-bicyclo[2.2.2]oct-2-en-3-yl)-2,3-dihydro-benzofuran-3-ol
    —— 2,3-Dihydro-5-hydroxy-6-<3-(2-hydroxymethylphenyl)-2-propenyl>benzofuran 120694-96-4 C18H18O3
    2,3-Dihydro-5-hydroxy-6-<3-(2-hydroxymethylphenyl)-2-propenyl>benzofuran
    —— 4,6,7-trichloro-2,5-dihydroxy-2,3-dihydrobenzo[b]furan 29262-98-4 C8H5Cl3O3
    4,6,7-trichloro-2,5-dihydroxy-2,3-dihydrobenzo[b]furan
    —— 4,5-(OCH2CH2)C6H3C(H)=N(2'-OH-5'-tBuC6H3) 1306773-32-9 C19H21NO2
    4,5-(OCH2CH2)C6H3C(H)=N(2'-OH-5'-tBuC6H3)
    —— bis(2,3-dihydrobenzofuran-5-yl)methanol 87901-66-4 C17H16O3
    bis(2,3-dihydrobenzofuran-5-yl)methanol
    —— 4,5-(OCH2CH2)C6H3C(H)=NCH2CH2NMe2 1306773-29-4 C13H18N2O
    4,5-(OCH2CH2)C6H3C(H)=NCH2CH2NMe2
    —— 1-[(1-benzyl-1H-tetrazol-5-yl)(2,3-dihydro-1-benzofuran-5-yl)methyl]-4-cyclobutyl-1,4-diazepane 1177251-90-9 C26H32N6O
    1-[(1-benzyl-1H-tetrazol-5-yl)(2,3-dihydro-1-benzofuran-5-yl)methyl]-4-cyclobutyl-1,4-diazepane
    —— 4-(2,3-dihydro-5-benzofuranyl)-2-butanone 465529-66-2 C12H14O2
    4-(2,3-dihydro-5-benzofuranyl)-2-butanone
    —— 1-(2,3-dihydrobenzofuran-5-yl)prop-2-en-1-ol 1282033-67-3 C11H12O2
    1-(2,3-dihydrobenzofuran-5-yl)prop-2-en-1-ol
    —— 5-(1,3-dithian-2-yl)-2,3-dihydrobenzofuran 1034669-88-9 C12H14OS2
    5-(1,3-dithian-2-yl)-2,3-dihydrobenzofuran
    —— 3,3-dimethyl-2-morpholin-4-yl-4-nitro-2H-benzofuran-5-ol 130399-36-9 C14H18N2O5
    3,3-dimethyl-2-morpholin-4-yl-4-nitro-2H-benzofuran-5-ol
    —— 5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one 1083088-66-7 C16H20N2O3
    5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one
    —— diethyl 1,6-dimethyl-6,8-dihydro-1H-2,5-dioxacyclohepta<jkl>-as-indacene-1,6-dicarboxylate 129579-36-8 C21H22O6
    diethyl 1,6-dimethyl-6,8-dihydro-1H-2,5-dioxacyclohepta<jkl>-as-indacene-1,6-dicarboxylate
    —— diethyl 6a,9a-dihydroxy-1,6-dimethyl-6,6a,7,8,9,9a-hexahydro-1H-2,5-dioxacyclohepta<jkl>-as-indacene-1,6-dicarboxylate 129579-40-4 C21H26O8
    diethyl 6a,9a-dihydroxy-1,6-dimethyl-6,6a,7,8,9,9a-hexahydro-1H-2,5-dioxacyclohepta<jkl>-as-indacene-1,6-dicarboxylate
    —— diethyl 6a,9a-dihydroxy-6,6a,7,8,9,9a-hexahydro-1H-2,5-dioxacyclohepta<jkl>-as-indacene-1,6-dicarboxylate 129579-39-1 C19H22O8
    diethyl 6a,9a-dihydroxy-6,6a,7,8,9,9a-hexahydro-1H-2,5-dioxacyclohepta<jkl>-as-indacene-1,6-dicarboxylate
    —— 3-methyl-3,3a,8a-trihydrobenzo[b]furano[3,2-d]furan-2-one 337973-19-0 C11H10O3
    3-methyl-3,3a,8a-trihydrobenzo[b]furano[3,2-d]furan-2-one
    —— 3-methyl-3-(phenylseleno)-3,3a,8a-trihydrobenzo[b]furano[3,2-d]furan-2-one 337973-20-3 C17H14O3Se
    3-methyl-3-(phenylseleno)-3,3a,8a-trihydrobenzo[b]furano[3,2-d]furan-2-one
    —— 7-methyl-2-phenylselanylmethyl-2,3-dihydrobenzofuran 71098-92-5 C16H16OSe
    7-methyl-2-phenylselanylmethyl-2,3-dihydrobenzofuran
    —— Ethyl 5-[[3-(aminomethyl)-4-hydroxyphenyl]methyl]-6,7-dichloro-2,3-dihydro-2-benzofurancarboxylate 742656-30-0 C19H19Cl2NO4
    Ethyl 5-[[3-(aminomethyl)-4-hydroxyphenyl]methyl]-6,7-dichloro-2,3-dihydro-2-benzofurancarboxylate
    —— 2,3-Dimethyl-2,3-dihydro-benzofuran-4-ol 89242-58-0 C10H12O2
    2,3-Dimethyl-2,3-dihydro-benzofuran-4-ol
    —— 7-chloro-2,3-dihydro-6-methyl-5-nitrobenzofuran-2-carboxylic acid methyl ester 88062-31-1 C11H10ClNO5
    7-chloro-2,3-dihydro-6-methyl-5-nitrobenzofuran-2-carboxylic acid methyl ester
    —— trifluoro-methanesulfonic acid 2,3-dihydro-benzofuran-6-yl ester 189035-25-4 C9H7F3O4S
    trifluoro-methanesulfonic acid 2,3-dihydro-benzofuran-6-yl ester
    —— 2-fluoro-6-(7-methoxy-2,3-dihydrobenzofuran-3-yloxy)-benzonitrile 872181-23-2 C16H12FNO3
    2-fluoro-6-(7-methoxy-2,3-dihydrobenzofuran-3-yloxy)-benzonitrile
    —— 2-(5-chloro-2,3-dihydro-benzofuran-3-yloxy)-6-fluoro-benzonitrile 872181-81-2 C15H9ClFNO2
    2-(5-chloro-2,3-dihydro-benzofuran-3-yloxy)-6-fluoro-benzonitrile
    —— 4,7-Difluoro-2,3-dihydro-2-hydroxymethylbenzofuran 196519-71-8 C9H8F2O2
    4,7-Difluoro-2,3-dihydro-2-hydroxymethylbenzofuran
    —— (+)-(3S)-3-hydroxy-2,3-dihydrobenzofuran 152560-12-8 C8H8O2
    (+)-(3S)-3-hydroxy-2,3-dihydrobenzofuran
    —— (-)-(3R)-3-hydroxy-2,3-dihydrobenzofuran 152560-17-3 C8H8O2
    (-)-(3R)-3-hydroxy-2,3-dihydrobenzofuran
    —— 1-(2,3-dihydro-1-benzofuran-5-yl)ethanone oxime 146321-88-2 C10H11NO2
    1-(2,3-dihydro-1-benzofuran-5-yl)ethanone oxime
    —— 2,3-dihydrobenzofuran-5-carbaldehyde oxime 882287-07-2 C9H9NO2
    2,3-dihydrobenzofuran-5-carbaldehyde oxime
    —— 1-(2,3-dihydrobenzofuran-5-yl)-3-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea 1442459-03-1 C16H20N4OS
    1-(2,3-dihydrobenzofuran-5-yl)-3-(3-(5-methyl-1H-imidazol-1-yl)propyl)thiourea
    —— 1,1,1-trifluoro-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-4-methylpentan-2-one 849353-53-3 C14H14ClF3O2
    1,1,1-trifluoro-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-4-methylpentan-2-one
    —— 7-(azidomethyl)-2,3-dihydro-1-benzofuran 870061-73-7 C9H9N3O
    7-(azidomethyl)-2,3-dihydro-1-benzofuran
    —— 4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one 609807-51-4 C14H15F3O2
    4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one
    —— methyl 5-Fluoro-2,3-dihydrobenzofuran-7-carboxylate 1616110-68-9 C10H9FO3
    methyl 5-Fluoro-2,3-dihydrobenzofuran-7-carboxylate
    —— 3-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(2,3-dihydrobenzofuran-5-yl) propan-1-one 1394204-82-0 C23H25NO2
    3-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(2,3-dihydrobenzofuran-5-yl) propan-1-one
    —— 5-nitro-2,3-dihydrobenzofuran-7-carboxamide 1616110-54-3 C9H8N2O4
    5-nitro-2,3-dihydrobenzofuran-7-carboxamide
    —— 1-(2,3-dihydrobenzofuran-5-yl)ethanone oxime —— C10H11NO2
    1-(2,3-dihydrobenzofuran-5-yl)ethanone oxime
    —— (1S,2S,3S,4R,5S)-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 1358579-26-6 C22H23ClO7
    (1S,2S,3S,4R,5S)-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
    —— [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 1358580-72-9 C43H41ClO7
    [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol