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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
    —— (S*)-N7-methyl-N5-(1-methyl-1H-pyrazol-4-yl)-3-phenyl-2,3-dihydrobenzofuran-5,7-dicarboxamide —— C21H20N4O3
    (S*)-N7-methyl-N5-(1-methyl-1H-pyrazol-4-yl)-3-phenyl-2,3-dihydrobenzofuran-5,7-dicarboxamide
    —— (-)-viminalin B —— C21H28O5
    (-)-viminalin B
    —— (R)-5,7-dimethyl-3-phenylthiomethyl-2,3-dihydrobenzofuran —— C17H18OS
    (R)-5,7-dimethyl-3-phenylthiomethyl-2,3-dihydrobenzofuran
    —— (7-tert-butoxycarbonylamino-4-methoxy-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-carbamic acid tert-butyl ester —— C21H32N2O6
    (7-tert-butoxycarbonylamino-4-methoxy-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-carbamic acid tert-butyl ester
    —— 2,3-dihydro-2,2,5,7-tetramethylbenzofuran —— C12H16O
    2,3-dihydro-2,2,5,7-tetramethylbenzofuran
    —— (4aRS,9bRS)-4a,9b-dihydro-2,6,8,9b-tetramethyl-4H-dibenzofuran-3-one —— C16H18O2
    (4aRS,9bRS)-4a,9b-dihydro-2,6,8,9b-tetramethyl-4H-dibenzofuran-3-one
    —— rac-3-((2R,3S)-2-cyclopropyl-3-phenyl-7-(3-(p-tolyl)ureido)-2,3-dihydrobenzofuran-5-yl)butanoic acid —— C29H30N2O4
    rac-3-((2R,3S)-2-cyclopropyl-3-phenyl-7-(3-(p-tolyl)ureido)-2,3-dihydrobenzofuran-5-yl)butanoic acid
    —— 2,2,5-trimethyl-3-(4-methylphenyl)-2,3-dihydrobenzofuran —— C18H20O
    2,2,5-trimethyl-3-(4-methylphenyl)-2,3-dihydrobenzofuran
    —— methyl [(3S)-6-{[(3R)-7-bromo-2,3-dihydro-1-benzofuran-3-yl](trifluoroacetyl)amino}-2,3-dihydro-1-benzofuran-3-yl]acetate —— C21H17BrF3NO5
    methyl [(3S)-6-{[(3R)-7-bromo-2,3-dihydro-1-benzofuran-3-yl](trifluoroacetyl)amino}-2,3-dihydro-1-benzofuran-3-yl]acetate
    —— methyl {(3S)-6-[(7-bromo-2,3-dihydro-1-benzofuran-3-yl)(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate —— C21H17BrF3NO5
    methyl {(3S)-6-[(7-bromo-2,3-dihydro-1-benzofuran-3-yl)(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate
    —— 3-phenyl-7-(4-(tetrahydrofuran-2-methoxy)phenyl)-3,7-dihydrobenzodifuran-2,6-dione —— C27H22O6
    3-phenyl-7-(4-(tetrahydrofuran-2-methoxy)phenyl)-3,7-dihydrobenzodifuran-2,6-dione
    —— (+/-)-2,3-dihydro-5-hydroxy-6,7-dimethyl-2-benzofuranacetic acid —— C12H14O4
    (+/-)-2,3-dihydro-5-hydroxy-6,7-dimethyl-2-benzofuranacetic acid
    —— 4-bromo-6-(bromodiphenylmethyl)-2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran —— C23H20Br2O3
    4-bromo-6-(bromodiphenylmethyl)-2-ethoxy-5-hydroxy-2,3-dihydrobenzofuran
    —— 3-(4-methoxybenzyl)-3-methoxycarbonyl-2,3-dihydrobenzofuran —— C18H18O4
    3-(4-methoxybenzyl)-3-methoxycarbonyl-2,3-dihydrobenzofuran
    —— 2,3-dihydro-6-(3-(4-propylphenoxy)propyl)-5-benzofuranol —— C20H24O3
    2,3-dihydro-6-(3-(4-propylphenoxy)propyl)-5-benzofuranol
    —— (3-methyl-2,3-dihydrobenzofuran-2-yl)methanol —— C10H12O2
    (3-methyl-2,3-dihydrobenzofuran-2-yl)methanol
    —— 6,7-dihydroxy-3,3-diphenyl-3<i>H</i>-benzofuran-2-one —— C20H14O4
    6,7-dihydroxy-3,3-diphenyl-3<i>H</i>-benzofuran-2-one
    —— (S)-2-methyl-2,3-dihydrobenzofuran-7-carboxamide —— C10H11NO2
    (S)-2-methyl-2,3-dihydrobenzofuran-7-carboxamide
    —— (R)-2-methyl-2,3-dihydrobenzofuran-7-carboxamide —— C10H11NO2
    (R)-2-methyl-2,3-dihydrobenzofuran-7-carboxamide
    —— N-(butylaminocarbonyl)-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide —— C15H22N2O4S
    N-(butylaminocarbonyl)-2,3-dihydro-2,2-dimethyl-7-benzofuransulfonamide
    —— 7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carbonyl chloride —— C12H13ClO3
    7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carbonyl chloride
    —— 2,3-Dihydro-2,2-dimethyl-7-methoxybenzofuran-4-carboxylic acid-N-3,5-dichloro-pyridin-4-ylamide —— C17H16Cl2N2O3
    2,3-Dihydro-2,2-dimethyl-7-methoxybenzofuran-4-carboxylic acid-N-3,5-dichloro-pyridin-4-ylamide
    —— 1,1'-spirodihydrobenzofuran-7,7'-diol —— C15H12O4
    1,1'-spirodihydrobenzofuran-7,7'-diol
    —— benzofuran-3(2H)-one O-methyloxime —— C9H9NO2
    benzofuran-3(2H)-one O-methyloxime
    —— (2RS,3RS)-5-bromo-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol —— C9H6BrF3O2
    (2RS,3RS)-5-bromo-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol
    —— (2RS,3RS)-7-(benzyloxy)-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol —— C16H13F3O3
    (2RS,3RS)-7-(benzyloxy)-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol
    —— (2RS,3RS)-5-chloro-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol —— C9H6ClF3O2
    (2RS,3RS)-5-chloro-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol
    —— (2RS,3RS)-5-methoxy-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol —— C10H9F3O3
    (2RS,3RS)-5-methoxy-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol
    —— (2RS,3RS)-5-methyl-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol —— C10H9F3O2
    (2RS,3RS)-5-methyl-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol
    —— (2RS,3RS)-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol —— C9H7F3O2
    (2RS,3RS)-3-(trifluoromethyl)-2,3-dihydrobenzofuran-2-ol
    —— (+/-)-2-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)ethylthio-2-thiazoline —— C17H23NO2S2
    (+/-)-2-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)ethylthio-2-thiazoline
    —— (+/-)-2-(2-bromoethyl)-2,3-dihydro-5-methoxy-4,6,7-trimethylbenzofuran —— C14H19BrO2
    (+/-)-2-(2-bromoethyl)-2,3-dihydro-5-methoxy-4,6,7-trimethylbenzofuran
    —— (2R)-4-acetyl-10-[2-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)acetyl]-5,13-dihydroxy-11-methoxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0<sup>2,7</sup>]trideca-1(9),4,6,10,12-pentaen-3-one —— C22H21NO7S2
    (2R)-4-acetyl-10-[2-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)acetyl]-5,13-dihydroxy-11-methoxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0<sup>2,7</sup>]trideca-1(9),4,6,10,12-pentaen-3-one
    —— cis-1,3,4-trimethyl-5a,6,7,8,9,9a-hexahydrodibenzofuran-2-ol —— C15H20O2
    cis-1,3,4-trimethyl-5a,6,7,8,9,9a-hexahydrodibenzofuran-2-ol
    —— 5,7-dimethyl-3-(5-methylthiophen-2-yl)-3-phenylbenzofuran-2(3H)-one —— C21H18O2S
    5,7-dimethyl-3-(5-methylthiophen-2-yl)-3-phenylbenzofuran-2(3H)-one
    —— tert-butyl rel-(1R,4aR,9bS)-1,2,4a,9b-tetrahydro-4-hydroxy-7,9-dimethoxy-1-(1-methylethyl)-3-dibenzofurancarboxylate —— C22H30O6
    tert-butyl rel-(1R,4aR,9bS)-1,2,4a,9b-tetrahydro-4-hydroxy-7,9-dimethoxy-1-(1-methylethyl)-3-dibenzofurancarboxylate
    —— ethyl rac-(1R,4aR,9bS)-1,2,4a,9b-tetrahydro-4-hydroxy-7,9-dimethoxy-1-(1-methylethyl)-3-dibenzofurancarboxylate —— C20H26O6
    ethyl rac-(1R,4aR,9bS)-1,2,4a,9b-tetrahydro-4-hydroxy-7,9-dimethoxy-1-(1-methylethyl)-3-dibenzofurancarboxylate
    —— (1S,4aS,9bR)-7,9-dimethoxy-1-(1-methylethyl)-1,2,3,4,4a,9b-hexahydrodibenzofuran-4-one —— C17H22O4
    (1S,4aS,9bR)-7,9-dimethoxy-1-(1-methylethyl)-1,2,3,4,4a,9b-hexahydrodibenzofuran-4-one
    —— 2-(6-((2-(4-methoxyphenyl)-4-methylthiazol-5-yl)methoxy)-2,3-dihydrobenzofuran-3-yl) acetic acid —— C22H21NO5S
    2-(6-((2-(4-methoxyphenyl)-4-methylthiazol-5-yl)methoxy)-2,3-dihydrobenzofuran-3-yl) acetic acid
    —— 2-(6-((2-(4-chlorophenyl)-4-methylthiazol-5-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid —— C21H18ClNO4S
    2-(6-((2-(4-chlorophenyl)-4-methylthiazol-5-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid
    —— N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)-1-hexadecanamide —— C28H47NO2
    N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)-1-hexadecanamide
    —— N-(2,2,6-trimethyl-2,3-dihydrobenzofuran-7-yl)hexadecaneamide —— C27H45NO2
    N-(2,2,6-trimethyl-2,3-dihydrobenzofuran-7-yl)hexadecaneamide
    —— 3-(3-Phenyl-2,3-dihydrobenzofuran-3-yl)-N,N-dimethylpropylamine oxalate —— C2H2O4*C19H23NO
    3-(3-Phenyl-2,3-dihydrobenzofuran-3-yl)-N,N-dimethylpropylamine oxalate
    —— (+/-)-2-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)ethylthio-2-pyrimidine —— C18H22N2O2S
    (+/-)-2-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)ethylthio-2-pyrimidine
    —— (S)-N-(2,3-dihydroxypropoxy)-7-fluoro-6-((2-fluoro-4-iodophenyl)amino)-2,3-dihydrobenzofuran-5-carboxamide —— C18H17F2IN2O5
    (S)-N-(2,3-dihydroxypropoxy)-7-fluoro-6-((2-fluoro-4-iodophenyl)amino)-2,3-dihydrobenzofuran-5-carboxamide
    —— 7-fluoro-6-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxyethoxy)-2,3-dihydrobenzofuran-5-carboxamide —— C17H15F2IN2O4
    7-fluoro-6-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxyethoxy)-2,3-dihydrobenzofuran-5-carboxamide
    —— (R)-N-(2,3-dihydroxypropoxy)-7-fluoro-6-((2-fluoro-4-iodophenyl)amino)-2,3-dihydrobenzofuran-5-carboxamide —— C18H17F2IN2O5
    (R)-N-(2,3-dihydroxypropoxy)-7-fluoro-6-((2-fluoro-4-iodophenyl)amino)-2,3-dihydrobenzofuran-5-carboxamide
    —— 2-ethoxy-2,3-dihydro-5-hydroxy-4,6-dimethylbenzofuran —— C12H16O3
    2-ethoxy-2,3-dihydro-5-hydroxy-4,6-dimethylbenzofuran
    —— 2-(1-piperidinyl)ethyl (+/-)-2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranacetate —— C21H31NO4
    2-(1-piperidinyl)ethyl (+/-)-2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranacetate
    —— 1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-4-piperidineethanol —— C20H32N2O2
    1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-4-piperidineethanol