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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
    —— 4-[([cyclopentyl-(2,3-dihydrobenzofuran-5-yl)methyl]{4-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]-3-methoxybenzyl}amino)methyl]benzoic acid —— C36H40N2O7
    4-[([cyclopentyl-(2,3-dihydrobenzofuran-5-yl)methyl]{4-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]-3-methoxybenzyl}amino)methyl]benzoic acid
    —— 8-methoxy-2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-carbonitrile —— C12H11NO3
    8-methoxy-2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-carbonitrile
    —— N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylamine hydrochloride —— C13H17Cl2NO*ClH
    N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylamine hydrochloride
    —— 2,4,6,7-tetramethyl-2,3-dihydro-benzofuran-5-ylamine —— C12H17NO
    2,4,6,7-tetramethyl-2,3-dihydro-benzofuran-5-ylamine
    —— 2,3-Dihydro-4-{3-[3-(methylthio)pyridyl]propyl}-5-benzofuranol —— C17H19NO2S
    2,3-Dihydro-4-{3-[3-(methylthio)pyridyl]propyl}-5-benzofuranol
    —— 3-acetyl-2,3-dihydrobenzofuran —— C10H10O3
    3-acetyl-2,3-dihydrobenzofuran
    —— ((3S)-2,3-dihydro-1-benzofuran-3-yl)ethanoic acid —— C10H10O3
    ((3S)-2,3-dihydro-1-benzofuran-3-yl)ethanoic acid
    —— 8-bromo-2-methoxy-N-(6-methylpyridin-2-yl)-4-oxo-6-(N-(2,4,4-trimethylpentan-2-yl)sulfamoyl)-1,4,4a,9b-tetrahydrodibenzo[b,d]-furan-4a-carboxamide —— C28H34BrN3O6S
    8-bromo-2-methoxy-N-(6-methylpyridin-2-yl)-4-oxo-6-(N-(2,4,4-trimethylpentan-2-yl)sulfamoyl)-1,4,4a,9b-tetrahydrodibenzo[b,d]-furan-4a-carboxamide
    —— aplysin —— C15H19BrO
    aplysin
    —— N-[3-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl]isonicotinamide hydrochloride —— C28H32N2O2*ClH
    N-[3-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl]isonicotinamide hydrochloride
    —— 1-(2,3-dihydrobenzofuran-3-yl)-N'-methyl-N'-phenylmethanesulfonohydrazide —— C16H18N2O3S
    1-(2,3-dihydrobenzofuran-3-yl)-N'-methyl-N'-phenylmethanesulfonohydrazide
    —— (+/-)-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine —— C15H12Cl2FNO
    (+/-)-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine
    —— 7-chloro-2,3-dihydro-1-benzofuran —— C8H7ClO
    7-chloro-2,3-dihydro-1-benzofuran
    —— 3-(4-chloropent-4-en-2-yl)-2,3-dihydrobenzofuran —— C13H15ClO
    3-(4-chloropent-4-en-2-yl)-2,3-dihydrobenzofuran
    —— 2,3-Dihydro-3,3-dimethyl-7-tert-butyl-5-(5-methyl-2-furoyl)benzo[b]furan —— C20H24O3
    2,3-Dihydro-3,3-dimethyl-7-tert-butyl-5-(5-methyl-2-furoyl)benzo[b]furan
    —— (S)-N-[N-(2,3-dihydrobenzofuran-4-yl)-pyrrolidin-3-yl]butyramide —— C16H22N2O2
    (S)-N-[N-(2,3-dihydrobenzofuran-4-yl)-pyrrolidin-3-yl]butyramide
    —— (R)-N-[N-(2,3-dihydrobenzofuran-4-yl)-pyrrolidin-3-yl]butyramide —— C16H22N2O2
    (R)-N-[N-(2,3-dihydrobenzofuran-4-yl)-pyrrolidin-3-yl]butyramide
    —— N-((7-(3-fluorophenyl)-2,3-dihydrobenzofuran-5-yl)methyl)pyridin-3-amine —— C20H17FN2O
    N-((7-(3-fluorophenyl)-2,3-dihydrobenzofuran-5-yl)methyl)pyridin-3-amine
    —— cis-9b-methyl-3,4,4a,9b-tetrahydrodibenzo[b,d]furan —— C13H14O
    cis-9b-methyl-3,4,4a,9b-tetrahydrodibenzo[b,d]furan
    —— 7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-(furan-2-ylthiocarbonyl)benzo[b]furan —— C19H22O3S
    7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-(furan-2-ylthiocarbonyl)benzo[b]furan
    —— 4-[2-(2,3-dihydro-2-methyl-5-benzofuranyl)ethyloxy]phenyl isocyanate —— C18H17NO3
    4-[2-(2,3-dihydro-2-methyl-5-benzofuranyl)ethyloxy]phenyl isocyanate
    —— 2,3-dihydro-5-methoxy-6-hydroxy-7-methyl-benzofuran —— C10H12O3
    2,3-dihydro-5-methoxy-6-hydroxy-7-methyl-benzofuran
    —— (3aRS,8aSR)-5-(tert-butyl-dimethylsilanyl)-7-ethoxy-6-methoxy-2,3,3a,8a-tetrahydro-1,8-dioxacyclopenta[a]inden-4-ol —— C19H30O5Si
    (3aRS,8aSR)-5-(tert-butyl-dimethylsilanyl)-7-ethoxy-6-methoxy-2,3,3a,8a-tetrahydro-1,8-dioxacyclopenta[a]inden-4-ol
    —— (4AS*,9BS*)-1,2,3,4,4a,9b-hexahydro-8-hydroxy-7-methyldibenzofuran-3-one —— C13H14O3
    (4AS*,9BS*)-1,2,3,4,4a,9b-hexahydro-8-hydroxy-7-methyldibenzofuran-3-one
    —— 2-amino-3-cyano-4-methyl-5-(6-chloro-2,3-dihydro-2, 2-dimethylbenzofuran-4-yl)pyridine —— C17H16ClN3O
    2-amino-3-cyano-4-methyl-5-(6-chloro-2,3-dihydro-2, 2-dimethylbenzofuran-4-yl)pyridine
    —— diisopropyl 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-3a,8b-dicarboxylate —— C19H24O5
    diisopropyl 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-3a,8b-dicarboxylate
    —— 2-(6-(2-phenoxyethoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid —— C18H18O5
    2-(6-(2-phenoxyethoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid
    —— 2,2-dimethyl-2,3-dihydrobenzofuran-7-yl 4-fluorophenethylcarbamate —— C19H20FNO3
    2,2-dimethyl-2,3-dihydrobenzofuran-7-yl 4-fluorophenethylcarbamate
    —— (R)-2-ethenyl-2-methyl-2,3-dihydrobenzofuran —— C11H12O
    (R)-2-ethenyl-2-methyl-2,3-dihydrobenzofuran
    —— (S)-2-ethenyl-2-methyl-2,3-dihydrobenzofuran —— C11H12O
    (S)-2-ethenyl-2-methyl-2,3-dihydrobenzofuran
    —— 3-(2H)-benzofuranthione —— C8H6OS
    3-(2H)-benzofuranthione
    —— (+/-)-{[7-(2,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine —— C15H13Cl2NO
    (+/-)-{[7-(2,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine
    —— 6-Cyclohexyl-2,3-dihydro-benzofuran —— C14H18O
    6-Cyclohexyl-2,3-dihydro-benzofuran
    —— 2-(6-((2-(3-chlorophenyl)-4-methylthiazol-5-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid —— C21H18ClNO4S
    2-(6-((2-(3-chlorophenyl)-4-methylthiazol-5-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid
    —— (E)-N-(coumaran-5-ylmethyl)-N-methyl-3-(4-biphenylyl)prop-2-en-1-amine lactate —— C3H6O3*C25H25NO
    (E)-N-(coumaran-5-ylmethyl)-N-methyl-3-(4-biphenylyl)prop-2-en-1-amine lactate
    —— (+/-)-5-hydroxy-3a-methyl-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran —— C11H12O3
    (+/-)-5-hydroxy-3a-methyl-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran
    —— 2,3-dihydro-6-phenylmethylthio-5-benzofuranol —— C15H14O2S
    2,3-dihydro-6-phenylmethylthio-5-benzofuranol
    —— 2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-carboxamide —— C11H11NO3
    2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-carboxamide
    —— 1-(7-tert-Butyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-(cyclopropylmethyl-methyl-amino)-ethanone —— C21H31NO2
    1-(7-tert-Butyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-(cyclopropylmethyl-methyl-amino)-ethanone
    —— 1-[(5-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl]piperazine —— C19H22N2O
    1-[(5-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl]piperazine
    —— (+)-5,6-dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindol-1,3(2H)-dione —— C30H31NO5
    (+)-5,6-dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindol-1,3(2H)-dione
    —— 2-[(E)-2-phenylethenyl]coumaran-5-ol —— C16H14O2
    2-[(E)-2-phenylethenyl]coumaran-5-ol
    —— tert-butyl N-[(3S)-6-formyl-2,3-dihydro-1-benzofuran-3-yl]carbamate —— C14H17NO4
    tert-butyl N-[(3S)-6-formyl-2,3-dihydro-1-benzofuran-3-yl]carbamate
    —— (E)-4-(2,3-dihydrobenzofuran-5-yl)-4-oxobut-2-enoic acid —— C12H10O4
    (E)-4-(2,3-dihydrobenzofuran-5-yl)-4-oxobut-2-enoic acid
    —— 5,6-dichloro-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione —— C28H25Cl2NO3
    5,6-dichloro-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione
    —— 4-[2-(2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-yl)vinyl]pyridine —— C17H15NO2
    4-[2-(2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-yl)vinyl]pyridine
    —— 2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione —— C28H27NO3
    2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione
    —— N-[3-(4-morpholinyl)propyl]-6,7-dihydrofuro[3,2-g][1,2,4]benzotriazin-3-amine 1-oxide —— C16H21N5O3
    N-[3-(4-morpholinyl)propyl]-6,7-dihydrofuro[3,2-g][1,2,4]benzotriazin-3-amine 1-oxide
    —— 7-heptyl-2,3-dihydro-6-methyl-4-phenyl-5-benzofuranol —— C22H28O2
    7-heptyl-2,3-dihydro-6-methyl-4-phenyl-5-benzofuranol
    —— (5-chloro-2,3-dihydrobenzofuran-2-yl)methanamine —— C9H10ClNO
    (5-chloro-2,3-dihydrobenzofuran-2-yl)methanamine