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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
    —— 1,1'-(3-(phenylamino)-2,3-dihydrobenzofuran-2,2-diyl)diethanone 1323141-95-2 C18H17NO3
    1,1'-(3-(phenylamino)-2,3-dihydrobenzofuran-2,2-diyl)diethanone
    —— 2-Benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde 109209-62-3 C16H14O2
    2-Benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde
    —— 2,2,6-trimethoxy-7-methyl-2,3-dihydrobenzo[b]furan-5-ol 260969-86-6 C12H16O5
    2,2,6-trimethoxy-7-methyl-2,3-dihydrobenzo[b]furan-5-ol
    —— (S)-N-(tert-butyl)-2-(2-((tert-butyldimethylsilyl)oxy)propan-2-yl)-4-methoxy-2,3-dihydrobenzofuran-7-carboxamide 1459804-93-3 C23H39NO4Si
    (S)-N-(tert-butyl)-2-(2-((tert-butyldimethylsilyl)oxy)propan-2-yl)-4-methoxy-2,3-dihydrobenzofuran-7-carboxamide
    —— (S)-N-(tert-butyl)-2-(2-((tert-butyldimethylsilyl)oxy)propan-2-yl)-6-((S)-2-hydroxypropyl)-4-methoxy-2,3-dihydrobenzofuran-7-carboxamide 1459804-95-5 C26H45NO5Si
    (S)-N-(tert-butyl)-2-(2-((tert-butyldimethylsilyl)oxy)propan-2-yl)-6-((S)-2-hydroxypropyl)-4-methoxy-2,3-dihydrobenzofuran-7-carboxamide
    —— (2,3-dihydrobenzofuran-3-yl)acetonitrile 131531-15-2 C10H9NO
    (2,3-dihydrobenzofuran-3-yl)acetonitrile
    —— 2-(2,3-dihydrobenzofuran-5-yl)-4-methylthiazole-5-carboxylic acid 1055043-17-8 C13H11NO3S
    2-(2,3-dihydrobenzofuran-5-yl)-4-methylthiazole-5-carboxylic acid
    —— 3-(1-ethyl-2-methanesulfinyl-cyclopropylmethyl)-2,3-dihydro-benzofuran 63755-77-1 C15H20O2S
    3-(1-ethyl-2-methanesulfinyl-cyclopropylmethyl)-2,3-dihydro-benzofuran
    —— 17,19-Etheno-22H-benzofuro[3a,3-n][1,5,10]triazacycloeicosine-3,14-dione,4,5,6,7,8,9,10,11,12,13,20a,21,23,24-tetradecahydro-22-hydroxy-,(1E,15E,20aR,22R,24aS)- (9CI) 24185-52-2 C25H33N3O4
    17,19-Etheno-22H-benzofuro[3a,3-n][1,5,10]triazacycloeicosine-3,14-dione,4,5,6,7,8,9,10,11,12,13,20a,21,23,24-tetradecahydro-22-hydroxy-,(1E,15E,20aR,22R,24aS)- (9CI)
    —— 4-(7,7-difluoro-5a,6,7,8,9,9a-hexahydrodibenzo[b,d]furan-9a-yl)phenol 1147714-60-0 C18H16F2O2
    4-(7,7-difluoro-5a,6,7,8,9,9a-hexahydrodibenzo[b,d]furan-9a-yl)phenol
    —— Ethyl cis-3-hydroxy-2,3-dihydro-2-benzofurancarboxylate 137514-36-4 C11H12O4
    Ethyl cis-3-hydroxy-2,3-dihydro-2-benzofurancarboxylate
    —— Ethyl trans-3-hydroxy-2,3-dihydro-2-benzofurancarboxylate 137514-36-4 C11H12O4
    Ethyl trans-3-hydroxy-2,3-dihydro-2-benzofurancarboxylate
    —— 7-(2-cyclohexenyl)-2,3-cyclohexano-2,3-dihydrobenzofuran 98382-17-3 C18H22O
    7-(2-cyclohexenyl)-2,3-cyclohexano-2,3-dihydrobenzofuran
    —— 5-(2-cyclohexenyl)-2,3-cyclohexano-2,3-dihydrobenzofuran 98382-18-4 C18H22O
    5-(2-cyclohexenyl)-2,3-cyclohexano-2,3-dihydrobenzofuran
    —— N-methyl-4-(2,3-dihydrobenzofuranyl)amine 389845-49-2 C10H13NO
    N-methyl-4-(2,3-dihydrobenzofuranyl)amine
    —— 1,2a,7b-trihydrobenzo[b]cyclobuta[1,2-d]furan-2-one 95123-37-8 C10H8O2
    1,2a,7b-trihydrobenzo[b]cyclobuta[1,2-d]furan-2-one
    —— 2,3-dihydro-2,2-dimethyl-7-iodobenzofuran 156632-76-7 C10H11IO
    2,3-dihydro-2,2-dimethyl-7-iodobenzofuran
    —— Pummerer's ketone 15413-34-0 C14H14O2
    Pummerer's ketone
    —— hydron;2-morpholin-4-ylethyl (2E)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;chloride —— C22H28ClNO4
    hydron;2-morpholin-4-ylethyl (2E)-2-(8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-ylidene)acetate;chloride
    —— (+/-)-4-[2-(tert-butyldimethylsilanyloxy)-3-formyl-2,3,3a,8a-tetrahydro-1H-8-oxa-cyclopenta[a]inden-7-yl]-butyric acid methyl ester —— C23H34O5Si
    (+/-)-4-[2-(tert-butyldimethylsilanyloxy)-3-formyl-2,3,3a,8a-tetrahydro-1H-8-oxa-cyclopenta[a]inden-7-yl]-butyric acid methyl ester
    —— trans-2-Ethyl-2,3-dihydro-3-benzofuranol 137556-60-6 C10H12O2
    trans-2-Ethyl-2,3-dihydro-3-benzofuranol
    —— 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionic acid 1005201-00-2 C13H12N2O4
    3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionic acid
    —— 3-(2,3-dihydrobenzofuran-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamide 609807-53-6 C15H21NO3
    3-(2,3-dihydrobenzofuran-7-yl)-3-methylbutanoic acid N,O-dimethylhydroxylamide
    —— 3-(2,3-dihydrobenzofuran-7-yl)-3-methylbutanoic acid 609807-52-5 C13H16O3
    3-(2,3-dihydrobenzofuran-7-yl)-3-methylbutanoic acid
    —— 1-[(3aS,8bS)-7-hydroxy-3a-morpholin-4-yl-1,2,3,8b-tetrahydrocyclopenta[b][1]benzofuran-8-yl]propan-1-one 93574-28-8 C18H23NO4
    1-[(3aS,8bS)-7-hydroxy-3a-morpholin-4-yl-1,2,3,8b-tetrahydrocyclopenta[b][1]benzofuran-8-yl]propan-1-one
    —— methyl 4-[(2,3-dihydrobenzofuran-3-yl)oxy]benzenepropanoate 691904-07-1 C18H18O4
    methyl 4-[(2,3-dihydrobenzofuran-3-yl)oxy]benzenepropanoate
    —— Magnum 50641-63-9 C23H26ClN3O6S
    Magnum
    —— (3aS,8bS)-7-chloro-3a-methyl-1,8b-dihydrofuro[3,4-b][1]benzofuran-3-one 59874-49-6 C11H9ClO3
    (3aS,8bS)-7-chloro-3a-methyl-1,8b-dihydrofuro[3,4-b][1]benzofuran-3-one
    —— 2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran 93885-43-9 C10H12O2
    2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran
    —— 2-(2-methyl-3H-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole 89197-31-9 C12H14N2O
    2-(2-methyl-3H-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole
    —— 3-({(2,3-dihydro-1-benzofuran-5-ylcarbonyl)[1-(4-fluorophenyl)ethyl]amino}methyl)benzoic acid 1398583-44-2 C25H22FNO4
    3-({(2,3-dihydro-1-benzofuran-5-ylcarbonyl)[1-(4-fluorophenyl)ethyl]amino}methyl)benzoic acid
    —— ethyl (2S,3S)-6-hydroxy-3-(prop-2-enoxycarbonylamino)-2,3-dihydro-1-benzofuran-2-carboxylate 957702-72-6 C15H17NO6
    ethyl (2S,3S)-6-hydroxy-3-(prop-2-enoxycarbonylamino)-2,3-dihydro-1-benzofuran-2-carboxylate
    —— (2R,3S)-N-[(4-bromophenyl)methyl]-2-ethenyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-amine 957266-73-8 C21H24BrNO4
    (2R,3S)-N-[(4-bromophenyl)methyl]-2-ethenyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-amine
    —— prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2R,3S)-2-ethenyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate 957266-70-5 C25H28BrNO6
    prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2R,3S)-2-ethenyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate
    —— prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-(hydroxymethyl)-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate 957702-51-1 C24H28BrNO7
    prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-(hydroxymethyl)-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate
    —— (E/Z)-6-benzyloxy-2,3-dihydrobenzofuran-3-oxime 139149-22-7 C15H13NO3
    (E/Z)-6-benzyloxy-2,3-dihydrobenzofuran-3-oxime
    —— (R)-6-benzyloxy-2,3-dihydrobenzofuran-3-ol 1034926-59-4 C15H14O3
    (R)-6-benzyloxy-2,3-dihydrobenzofuran-3-ol
    —— methyl 6-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate 1350933-37-7 C10H10O4
    methyl 6-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate
    —— (E)-3-(3,5-dimethyl-2,3-dihydrobenzofuran-4-yl)acrylonitrile 1092107-93-1 C13H13NO
    (E)-3-(3,5-dimethyl-2,3-dihydrobenzofuran-4-yl)acrylonitrile
    —— (2R,3R)-3-[(R)-(E)-bis-(tert-butyldimethylsilanyloxy)-methylpent-3-enyl]-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran 628299-81-0 C37H69BrO4Si3
    (2R,3R)-3-[(R)-(E)-bis-(tert-butyldimethylsilanyloxy)-methylpent-3-enyl]-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran
    —— (2R,3S)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile 474418-78-5 C20H30BrNO2Si
    (2R,3S)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile
    —— 2-methylacrylic acid (R)-1-((2R,3R)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)-but-3-enyl ester 628299-84-3 C27H41BrO4Si
    2-methylacrylic acid (R)-1-((2R,3R)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)-but-3-enyl ester
    —— (2R,3R)-3-[(R)-(Z)-bis-(tert-butyldimethylsilanyloxy)-methylpent-3-enyl]-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran 628299-88-7 C37H69BrO4Si3
    (2R,3R)-3-[(R)-(Z)-bis-(tert-butyldimethylsilanyloxy)-methylpent-3-enyl]-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran
    —— (2R)-2-[(2R,3R)-7-bromo-2,3-dimethyl-4-tri(propan-2-yl)silyloxy-2H-1-benzofuran-3-yl]-5-methyl-2,3-dihydropyran-6-one 628299-85-4 C25H37BrO4Si
    (2R)-2-[(2R,3R)-7-bromo-2,3-dimethyl-4-tri(propan-2-yl)silyloxy-2H-1-benzofuran-3-yl]-5-methyl-2,3-dihydropyran-6-one
    —— (R)-1-((2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)but-3-en-1-ol 628299-76-3 C23H37BrO3Si
    (R)-1-((2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)but-3-en-1-ol
    —— (-)-6,7-dichloro-2,3-dihydro-5-(2-thienylcarbonyl)-2-benzofurancarboxylic acid 62717-25-3 C14H8Cl2O4S
    (-)-6,7-dichloro-2,3-dihydro-5-(2-thienylcarbonyl)-2-benzofurancarboxylic acid
    —— 6,7-dichloro-2,3-dihydro-5-(2-thienylcarbonyl)-2-bezofurancarboxamide 77886-69-2 C14H9Cl2NO3S
    6,7-dichloro-2,3-dihydro-5-(2-thienylcarbonyl)-2-bezofurancarboxamide
    —— 6,7-Dichloro-2,3-dihydro-5-<3-(1,2,5-thiadiazolyl)-carbonyl>-benzofuran-2-carbonic acid 62717-21-9 C12H6Cl2N2O4S
    6,7-Dichloro-2,3-dihydro-5-<3-(1,2,5-thiadiazolyl)-carbonyl>-benzofuran-2-carbonic acid
    —— 6,7-dichloro-2,3-dihydro-5-(2-thienylsulfonyl)-2-benzofurancarboxylic acid 77514-34-2 C13H8Cl2O5S2
    6,7-dichloro-2,3-dihydro-5-(2-thienylsulfonyl)-2-benzofurancarboxylic acid
    —— 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carbonyl chloride 70261-96-0 C14H7Cl3O3S
    6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carbonyl chloride