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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
    —— 5,7-Dihydroxy-4a,9a-dihydro-[2]benzofuro[6,5-b][1]benzofuran-4,10-dione —— C14H8O6
    5,7-Dihydroxy-4a,9a-dihydro-[2]benzofuro[6,5-b][1]benzofuran-4,10-dione
    —— methyl 2-[(3S)-6-[(1R,3Z,5Z)-6-(6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-5-ylmethyl)-2-methylidene-5-(trifluoromethyl)cyclonona-3,5-dien-1-yl]oxy-2,3-dihydro-1-benzofuran-3-yl]acetate —— C29H31F3N2O4S
    methyl 2-[(3S)-6-[(1R,3Z,5Z)-6-(6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-5-ylmethyl)-2-methylidene-5-(trifluoromethyl)cyclonona-3,5-dien-1-yl]oxy-2,3-dihydro-1-benzofuran-3-yl]acetate
    —— 2,2-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-1-benzofuran-7-carbonitrile —— C17H22BNO3
    2,2-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-1-benzofuran-7-carbonitrile
    —— 7-cyano-2,2-diethyl-3H-1-benzofuran-5-carboxamide —— C14H16N2O2
    7-cyano-2,2-diethyl-3H-1-benzofuran-5-carboxamide
    —— Ethyl 2-(7-cyano-2-methyl-2,3-dihydro-1-benzofuran-5-yl)-4-methyl-1,3-thiazole-5-carboxylate —— C17H16N2O3S
    Ethyl 2-(7-cyano-2-methyl-2,3-dihydro-1-benzofuran-5-yl)-4-methyl-1,3-thiazole-5-carboxylate
    —— 2-ethyl-2-methyl-3H-1-benzofuran-5-carbonitrile —— C12H13NO
    2-ethyl-2-methyl-3H-1-benzofuran-5-carbonitrile
    —— 7-cyano-2,2-diethyl-3H-1-benzofuran-5-carbothioamide —— C14H16N2OS
    7-cyano-2,2-diethyl-3H-1-benzofuran-5-carbothioamide
    —— 2-(7-Cyano-2-methyl-2,3-dihydro-1-benzofuran-5-yl)-4-methyl-1,3-thiazole-5-carboxylic acid —— C15H12N2O3S
    2-(7-Cyano-2-methyl-2,3-dihydro-1-benzofuran-5-yl)-4-methyl-1,3-thiazole-5-carboxylic acid
    —— 7-cyano-2-ethyl-2-methyl-3H-1-benzofuran-5-carbothioamide —— C13H14N2OS
    7-cyano-2-ethyl-2-methyl-3H-1-benzofuran-5-carbothioamide
    —— 7-cyano-2,2-dimethyl-3H-1-benzofuran-5-carbothioamide —— C12H12N2OS
    7-cyano-2,2-dimethyl-3H-1-benzofuran-5-carbothioamide
    —— 5-formyl-2,2-dimethyl-3H-1-benzofuran-7-carbonitrile —— C12H11NO2
    5-formyl-2,2-dimethyl-3H-1-benzofuran-7-carbonitrile
    —— 7-cyano-2,2-dimethyl-3H-1-benzofuran-5-carboxylic acid —— C12H11NO3
    7-cyano-2,2-dimethyl-3H-1-benzofuran-5-carboxylic acid
    —— 4-[(2E,3R)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholine —— C20H18ClFN2O5
    4-[(2E,3R)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholine
    —— 4-[(2E,3S)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholine —— C20H18ClFN2O5
    4-[(2E,3S)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholine
    —— 4-[(2E,3R)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium —— C20H19ClFN2O5+
    4-[(2E,3R)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium
    —— 4-[(2E,3S)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium —— C20H19ClFN2O5+
    4-[(2E,3S)-5-chloro-2-[2-(4-fluorophenoxy)ethylidene]-7-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium
    —— (2-chloropyrimidin-4-yl)-(2,2-dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)amine 1417883-90-9 C15H16ClN3O
    (2-chloropyrimidin-4-yl)-(2,2-dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)amine
    —— 6-Tert-butyl-2-propan-2-yl-2,3-dihydro-1-benzofuran —— C15H22O
    6-Tert-butyl-2-propan-2-yl-2,3-dihydro-1-benzofuran
    —— Methyl 2,3-dihydro-4-hydroxy-7-benzofurancarboxylate 1620412-65-8 C10H10O4
    Methyl 2,3-dihydro-4-hydroxy-7-benzofurancarboxylate
    —— 7-(Chloromethyl)-4-propan-2-yloxy-2,3-dihydro-1-benzofuran —— C12H15ClO2
    7-(Chloromethyl)-4-propan-2-yloxy-2,3-dihydro-1-benzofuran
    —— N-[2-amino-2-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide —— C23H28N4O3
    N-[2-amino-2-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethyl]-2,3-dihydro-1-benzofuran-3-carboxamide
    —— 2-[[2,3-dihydro-4-(trifluoromethyl)-2-benzofuranyl]methyl]-3,4-dihydro-7-(4-methyl-1H-imidazol-1-yl)-2H-pyrido[1,2-a]pyrazine-1,6-dione 1620411-48-4 C22H19F3N4O3
    2-[[2,3-dihydro-4-(trifluoromethyl)-2-benzofuranyl]methyl]-3,4-dihydro-7-(4-methyl-1H-imidazol-1-yl)-2H-pyrido[1,2-a]pyrazine-1,6-dione
    —— (3R)-2-[[2,3-dihydro-4-(1-methylethoxy)-7-benzofuranyl]methyl]-3,4-dihydro-3-methyl-7-(4-methyl-1H-imidazol-1-yl)-2H-pyrido[1,2-a]pyrazine-1,6-dione 1620411-46-2 C25H28N4O4
    (3R)-2-[[2,3-dihydro-4-(1-methylethoxy)-7-benzofuranyl]methyl]-3,4-dihydro-3-methyl-7-(4-methyl-1H-imidazol-1-yl)-2H-pyrido[1,2-a]pyrazine-1,6-dione
    —— (3R)-2-[5,7-bis(trifluoromethyl)-2,3-dihydro-1-benzofuran-3-yl]-3-methyl-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione —— C23H18F6N4O3
    (3R)-2-[5,7-bis(trifluoromethyl)-2,3-dihydro-1-benzofuran-3-yl]-3-methyl-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione
    —— (3R)-2-[(5-bromo-2,3-dihydro-7-benzofuranyl)methyl]-3,4-dihydro-3-methyl-7-(4-methyl-1H-imidazol-1-yl)-2H-pyrido [1,2-a]pyrazine-1,6-dione 1620411-15-5 C22H21BrN4O3
    (3R)-2-[(5-bromo-2,3-dihydro-7-benzofuranyl)methyl]-3,4-dihydro-3-methyl-7-(4-methyl-1H-imidazol-1-yl)-2H-pyrido [1,2-a]pyrazine-1,6-dione
    —— 2-[5,7-Bis(trifluoromethyl)-2,3-dihydro-1-benzofuran-3-yl]-3-methyl-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione —— C23H18F6N4O3
    2-[5,7-Bis(trifluoromethyl)-2,3-dihydro-1-benzofuran-3-yl]-3-methyl-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione
    —— 2-[4,6-Bis(trifluoromethyl)-2,3-dihydro-1-benzofuran-3-yl]-3-methyl-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione —— C23H18F6N4O3
    2-[4,6-Bis(trifluoromethyl)-2,3-dihydro-1-benzofuran-3-yl]-3-methyl-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione
    —— (3S)-3-(4-chlorophenyl)-3-(2,3-dihydro-1-benzofuran-5-yl)-N-[5-fluoro-4-[2-[(2R,5S)-5-methylmorpholin-2-yl]ethyl]pyridin-3-yl]propanamide —— C29H31ClFN3O3
    (3S)-3-(4-chlorophenyl)-3-(2,3-dihydro-1-benzofuran-5-yl)-N-[5-fluoro-4-[2-[(2R,5S)-5-methylmorpholin-2-yl]ethyl]pyridin-3-yl]propanamide
    —— 2,2,3,3,5,6-Hexamethyl-1-benzofuran —— C14H20O
    2,2,3,3,5,6-Hexamethyl-1-benzofuran
    —— 2-ethoxy-3,3,6-trimethyl-2H-1-benzofuran-5-ol —— C13H18O3
    2-ethoxy-3,3,6-trimethyl-2H-1-benzofuran-5-ol
    —— (4E)-1-(3,5-dichlorophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H14Cl2N2O3
    (4E)-1-(3,5-dichlorophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— (4E)-1-(4-bromophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H15BrN2O3
    (4E)-1-(4-bromophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— (4E)-1-(3,5-dichlorophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H14Cl2N2O3
    (4E)-1-(3,5-dichlorophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— (4Z)-1-(4-bromophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H15BrN2O3
    (4Z)-1-(4-bromophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— (4Z)-1-(3,5-dichlorophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H14Cl2N2O3
    (4Z)-1-(3,5-dichlorophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— (4E)-1-(4-bromophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H15BrN2O3
    (4E)-1-(4-bromophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— (4Z)-1-(4-bromophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H15BrN2O3
    (4Z)-1-(4-bromophenyl)-4-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— (4Z)-1-(3,5-dichlorophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione —— C19H14Cl2N2O3
    (4Z)-1-(3,5-dichlorophenyl)-4-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]pyrazolidine-3,5-dione
    —— 10-[(Z)-but-2-enylidene]-9,13,13-trimethyl-8-oxatetracyclo[7.5.0.01,11.02,7]tetradeca-2,4,6,11-tetraene —— C20H22O
    10-[(Z)-but-2-enylidene]-9,13,13-trimethyl-8-oxatetracyclo[7.5.0.01,11.02,7]tetradeca-2,4,6,11-tetraene
    —— 3,3-difluoro-4-methyl-2H-1-benzofuran —— C9H8F2O
    3,3-difluoro-4-methyl-2H-1-benzofuran
    —— 4-[(2Z,3R)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholine —— C20H18Cl2N2O5
    4-[(2Z,3R)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholine
    —— 4-[(2Z,3R)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium —— C20H19Cl2N2O5+
    4-[(2Z,3R)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium
    —— 4-[(2Z,3S)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholine —— C20H18Cl2N2O5
    4-[(2Z,3S)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholine
    —— 4-[(2Z,3S)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium —— C20H19Cl2N2O5+
    4-[(2Z,3S)-2-[2-(2,4-dichlorophenoxy)ethylidene]-5-nitro-3H-1-benzofuran-3-yl]morpholin-4-ium
    —— ethyl (1S,2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxylate —— C14H16O3
    ethyl (1S,2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxylate
    —— N-[[(2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide —— C15H19NO2
    N-[[(2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide
    —— ethyl (2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxylate —— C14H16O3
    ethyl (2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxylate
    —— (1S,2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxamide —— C12H13NO2
    (1S,2S)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropane-1-carboxamide
    —— (1S,2S)-2-(2,3-Dihydrobenzofuran-4-yl)cyclopropane-1-carboxylic acid —— C12H12O3
    (1S,2S)-2-(2,3-Dihydrobenzofuran-4-yl)cyclopropane-1-carboxylic acid
    —— Tesimeltion Enantiomer —— C15H19NO2
    Tesimeltion Enantiomer