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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
    —— 2-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]sulfonylethyl]acetamide —— C18H26N2O5S
    2-(2,3-dihydro-1-benzofuran-5-yl)-N-[2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]sulfonylethyl]acetamide
    —— (3R)-1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3-methylpiperidine —— C14H19NO3S
    (3R)-1-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-3-methylpiperidine
    —— (2R,3S)-5-bromo-2-[(S)-hydroxy(phenyl)methyl]-2-(1,2,4-triazol-1-ylmethyl)-3H-1-benzofuran-3-ol —— C18H16BrN3O3
    (2R,3S)-5-bromo-2-[(S)-hydroxy(phenyl)methyl]-2-(1,2,4-triazol-1-ylmethyl)-3H-1-benzofuran-3-ol
    —— (4E,5R)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-[[(2S)-oxolan-2-yl]methyl]pyrrolidine-2,3-dione —— C23H23NO6
    (4E,5R)-5-(furan-2-yl)-4-[hydroxy-[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]-1-[[(2S)-oxolan-2-yl]methyl]pyrrolidine-2,3-dione
    —— (2S)-5-chloro-N-(2-methoxypyridin-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H13ClN2O3
    (2S)-5-chloro-N-(2-methoxypyridin-3-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S)-5-chloro-N-[(2S)-2-morpholin-4-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C16H21ClN2O3
    (2S)-5-chloro-N-[(2S)-2-morpholin-4-ylpropyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[(1S)-1-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)ethyl]-2,3-dihydro-1-benzofuran-5-amine —— C15H19N3O2
    N-[(1S)-1-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)ethyl]-2,3-dihydro-1-benzofuran-5-amine
    —— N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-methyl-1,2-oxazole-3-carboxamide —— C14H14N2O3
    N-[[(2R)-2,3-dihydro-1-benzofuran-2-yl]methyl]-5-methyl-1,2-oxazole-3-carboxamide
    —— N-[(1R)-1-[(2S)-oxolan-2-yl]ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C14H19NO4S
    N-[(1R)-1-[(2S)-oxolan-2-yl]ethyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (2R)-N-[(2R)-2-(dimethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C17H20N2O2S
    (2R)-N-[(2R)-2-(dimethylamino)-2-thiophen-3-ylethyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S,5R)-4-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-2,5-dimethylmorpholine —— C14H19NO4S
    (2S,5R)-4-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-2,5-dimethylmorpholine
    —— (2R)-5-chloro-N-(1H-1,2,4-triazol-5-yl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C11H9ClN4O2
    (2R)-5-chloro-N-(1H-1,2,4-triazol-5-yl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2R,5R)-4-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-2,5-dimethylmorpholine —— C14H19NO4S
    (2R,5R)-4-(2,3-dihydro-1-benzofuran-5-ylsulfonyl)-2,5-dimethylmorpholine
    —— (2S)-N-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C15H16N4O2
    (2S)-N-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (2S,3S)-2,3-dimethyl-N-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C16H21NO4S
    (2S,3S)-2,3-dimethyl-N-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2S,3R)-2,3-dimethyl-N-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]-2,3-dihydro-1-benzofuran-7-carboxamide —— C16H21NO4S
    (2S,3R)-2,3-dimethyl-N-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]-2,3-dihydro-1-benzofuran-7-carboxamide
    —— (2R)-N-[[2-(imidazol-1-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C20H19N3O2
    (2R)-N-[[2-(imidazol-1-ylmethyl)phenyl]methyl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[3-[[(2S)-oxolan-2-yl]methoxy]propyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C16H23NO5S
    N-[3-[[(2S)-oxolan-2-yl]methoxy]propyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (2R)-5-chloro-N-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide —— C14H16ClNO4S
    (2R)-5-chloro-N-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]-2,3-dihydro-1-benzofuran-2-carboxamide
    —— N-[[(2R)-oxolan-2-yl]methyl]-2,3-dihydro-1-benzofuran-5-sulfonamide —— C13H17NO4S
    N-[[(2R)-oxolan-2-yl]methyl]-2,3-dihydro-1-benzofuran-5-sulfonamide
    —— (2S)-5-chloro-N-(1H-pyrazol-5-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide —— C13H12ClN3O2
    (2S)-5-chloro-N-(1H-pyrazol-5-ylmethyl)-2,3-dihydro-1-benzofuran-2-carboxamide
    —— (6-Methoxy-2-hydrobenzo[b]furan-3-ylidene)azamethyl 2-chloroacetate —— C11H10ClNO4
    (6-Methoxy-2-hydrobenzo[b]furan-3-ylidene)azamethyl 2-chloroacetate
    —— (5E)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C13H11NO2S2
    (5E)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
    —— 1-{(5E)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}piperidine-4-carboxamide —— C19H21N3O3S
    1-{(5E)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}piperidine-4-carboxamide
    —— (5E)-3-(3-methoxypropyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one —— C17H19NO3S2
    (5E)-3-(3-methoxypropyl)-5-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methylidene]-2-thioxo-1,3-thiazolidin-4-one
    —— 2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-[(5Z)-2,4-dioxo-5-[(3,4,5-trimethoxyphenyl)methylidene]-1,3-thiazolidin-3-yl]ethyl]acetamide —— C27H30N2O8S
    2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]-N-[2-[(5Z)-2,4-dioxo-5-[(3,4,5-trimethoxyphenyl)methylidene]-1,3-thiazolidin-3-yl]ethyl]acetamide
    —— methyl (9Z)-9-(3,5-dichloro-2-hydroxybenzylidene)-6a-methyl-10-oxo-6,6a,9,10-tetrahydro-11aH-[1]benzofuro[2,3-e]cyclopropa[d][1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H16Cl2N2O5S
    methyl (9Z)-9-(3,5-dichloro-2-hydroxybenzylidene)-6a-methyl-10-oxo-6,6a,9,10-tetrahydro-11aH-[1]benzofuro[2,3-e]cyclopropa[d][1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
    —— 2-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]propanedinitrile —— C13H10N2O
    2-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methylidene]propanedinitrile
    —— N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-[(6-methyl-4-oxo-1H-pyrimidin-2-yl)sulfanyl]acetamide —— C17H19N3O3S
    N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]-2-[(6-methyl-4-oxo-1H-pyrimidin-2-yl)sulfanyl]acetamide
    —— 2-(2-chlorophenoxy)-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide —— C18H18ClNO3
    2-(2-chlorophenoxy)-N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide
    —— 2-(4-chlorophenoxy)-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide —— C18H18ClNO3
    2-(4-chlorophenoxy)-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide
    —— (2S)-N-[(2-fluorophenyl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5-carboxamide —— C17H16FNO2
    (2S)-N-[(2-fluorophenyl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5-carboxamide
    —— N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]thiophene-2-carboxamide —— C15H15NO2S
    N-[[(2S)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]thiophene-2-carboxamide
    —— (2R)-N-[(2-chlorophenyl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5-carboxamide —— C17H16ClNO2
    (2R)-N-[(2-chlorophenyl)methyl]-2-methyl-2,3-dihydro-1-benzofuran-5-carboxamide
    —— 2-(4-cyclohexylphenoxy)-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide —— C24H29NO3
    2-(4-cyclohexylphenoxy)-N-[[(2R)-2-methyl-2,3-dihydro-1-benzofuran-5-yl]methyl]acetamide
    —— (2S)-7-methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acid —— C10H10O4
    (2S)-7-methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acid
    —— 4-[(2R)-2,3-dihydro-1-benzofuran-2-yl]pyridine —— C13H11NO
    4-[(2R)-2,3-dihydro-1-benzofuran-2-yl]pyridine
    —— Methyl 5-{(Z)-1-[5-(3-chlorophenyl)-2-furyl]methylidene}-2A-methyl-6-oxo-2,2A-dihydro-7AH-[1]benzofuro[2,3-E]cyclopropa[D][1,3]thiazolo[3,2-A]pyrimidine-2(6H)-carboxylate —— C27H19ClN2O5S
    Methyl 5-{(Z)-1-[5-(3-chlorophenyl)-2-furyl]methylidene}-2A-methyl-6-oxo-2,2A-dihydro-7AH-[1]benzofuro[2,3-E]cyclopropa[D][1,3]thiazolo[3,2-A]pyrimidine-2(6H)-carboxylate
    —— (3R)-3-[(dimethylamino)methyl]-2,2-dimethyl-3H-1-benzofuran-5-ol —— C13H19NO2
    (3R)-3-[(dimethylamino)methyl]-2,2-dimethyl-3H-1-benzofuran-5-ol
    —— (3R)-3-propan-2-yl-2,3-dihydro-1-benzofuran —— C11H14O
    (3R)-3-propan-2-yl-2,3-dihydro-1-benzofuran
    —— (2S)-2-ethoxy-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-ol —— C12H16O3
    (2S)-2-ethoxy-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-ol
    —— (4aS,9bS)-dibenzofuran-4a,9b-diol —— C12H10O3
    (4aS,9bS)-dibenzofuran-4a,9b-diol
    —— (4aS,9bR)-dibenzofuran-4a,9b-diol —— C12H10O3
    (4aS,9bR)-dibenzofuran-4a,9b-diol
    —— (2S)-2-(2,3-dihydro-1-benzofuran-7-yloxy)propan-1-amine —— C11H15NO2
    (2S)-2-(2,3-dihydro-1-benzofuran-7-yloxy)propan-1-amine
    —— (2R)-2-(2,3-dihydro-1-benzofuran-7-yloxy)propan-1-amine —— C11H15NO2
    (2R)-2-(2,3-dihydro-1-benzofuran-7-yloxy)propan-1-amine
    —— (2S)-6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-5-ol —— C10H12O3
    (2S)-6-methoxy-2-methyl-2,3-dihydro-1-benzofuran-5-ol
    —— (2S)-2-ethyl-5-methoxy-3-methylidene-1-benzofuran —— C12H14O2
    (2S)-2-ethyl-5-methoxy-3-methylidene-1-benzofuran
    —— (3Z)-3-[(2-methylanilino)methylidene]-1-benzofuran-2-thione —— C16H13NOS
    (3Z)-3-[(2-methylanilino)methylidene]-1-benzofuran-2-thione
    —— 2-chloro-1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]ethanone —— C10H9ClO2
    2-chloro-1-[(2S)-2,3-dihydro-1-benzofuran-2-yl]ethanone
    —— [(4aS,9bS)-9bH-dibenzofuran-4a-yl]hydrazine —— C12H12N2O
    [(4aS,9bS)-9bH-dibenzofuran-4a-yl]hydrazine