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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
    —— 936214-83-4 C20H26N2O
    —— 2,3-dihydro-2-oxo-3-phenyl-3-benzofurancarboxylic acid, phenyl ester 110745-17-0 C21H14O4
    2,3-dihydro-2-oxo-3-phenyl-3-benzofurancarboxylic acid, phenyl ester
    —— (R)-4-Hydroxy-2-isopropyl-2,3-dihydro-benzofuran-5-carbaldehyde 14702-52-4 C12H14O3
    (R)-4-Hydroxy-2-isopropyl-2,3-dihydro-benzofuran-5-carbaldehyde
    —— 5'-benzyl 3'-methyl (3R,4'S,5'R)-2-oxo-4'-phenyl-2H-spiro[benzofuran-3,1'-cyclopentan]-2'-ene-3',5'-dicarboxylate 1440545-09-4 C28H22O6
    5'-benzyl 3'-methyl (3R,4'S,5'R)-2-oxo-4'-phenyl-2H-spiro[benzofuran-3,1'-cyclopentan]-2'-ene-3',5'-dicarboxylate
    —— 1242046-79-2 C22H17NO4
    —— 1-(3-bromo-4-azidophenyl)-4-(t-butyl)-2,6,7-trioxabicyclo<2.2.2>octane 140635-75-2 C15H18BrN3O3
    1-(3-bromo-4-azidophenyl)-4-(t-butyl)-2,6,7-trioxabicyclo<2.2.2>octane
    —— methyl 2-(4-(2,3-dihydrobenzofuran-5-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate 1265397-75-8 C25H26N2O3
    methyl 2-(4-(2,3-dihydrobenzofuran-5-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate
    —— 5-(1-Chloro-2,2,2-trifluoro-1-p-tolyl-ethyl)-2,3-dihydro-benzofuran 131543-76-5 C17H14ClF3O
    5-(1-Chloro-2,2,2-trifluoro-1-p-tolyl-ethyl)-2,3-dihydro-benzofuran
    —— 2,6-dichloro-4-(3-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yloxy)methyl)-1,2,4-triazin-6-yl)phenol 1191246-81-7 C20H17Cl2N3O3
    2,6-dichloro-4-(3-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yloxy)methyl)-1,2,4-triazin-6-yl)phenol
    —— 936214-81-2 C19H24N2O
    —— 3-Chloro-1-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)propan-1-one 111038-50-7 C12H13ClO2
    3-Chloro-1-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)propan-1-one
    —— 4-(2,3-dihydro-5-fluoro-benzofuran-3-yl)butyronitrile 147373-18-0 C12H12FNO
    4-(2,3-dihydro-5-fluoro-benzofuran-3-yl)butyronitrile
    —— Acetic acid (5aS,7S,9aR)-7-acetoxy-9a-(2-iodo-ethyl)-3-methoxy-5a,6,7,8,9,9a-hexahydro-dibenzofuran-2-yl ester 127826-22-6 C19H23IO6
    Acetic acid (5aS,7S,9aR)-7-acetoxy-9a-(2-iodo-ethyl)-3-methoxy-5a,6,7,8,9,9a-hexahydro-dibenzofuran-2-yl ester
    —— 5,7-di-tert-butyl-3-(4-methoxycarbonylphenyl)-3H-benzofuran-2-one 353505-23-4 C24H28O4
    5,7-di-tert-butyl-3-(4-methoxycarbonylphenyl)-3H-benzofuran-2-one
    —— 2-Carboxy-3-cyclohexyl-2,3-dihydrobenzo<b>furan 344441-62-9 C15H18O3
    2-Carboxy-3-cyclohexyl-2,3-dihydrobenzo<b>furan
    —— 6,7-Dichloro-5-(2-ethoxycarbonyl-acetyl)-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester 126200-81-5 C16H16Cl2O6
    6,7-Dichloro-5-(2-ethoxycarbonyl-acetyl)-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester
    —— N'-(3-cyano-3,4-dihydro-2H-chromen-2-yl)-N,N-dimethylimidoformamide 1228595-08-1 C13H15N3O
    N'-(3-cyano-3,4-dihydro-2H-chromen-2-yl)-N,N-dimethylimidoformamide
    —— (1S,2S)-1,2-Diphenyl-1,2-dihydro-benzo[f]chromen-3-one 81009-11-2 C25H18O2
    (1S,2S)-1,2-Diphenyl-1,2-dihydro-benzo[f]chromen-3-one
    —— 6,7-Dichloro-5-{(2-chloro-phenyl)-[(Z)-hydroxyimino]-methyl}-2,3-dihydro-benzofuran-2-carboxylic acid 90246-68-7 C16H10Cl3NO4
    6,7-Dichloro-5-{(2-chloro-phenyl)-[(Z)-hydroxyimino]-methyl}-2,3-dihydro-benzofuran-2-carboxylic acid
    —— 3-Phenyl-2,3-dihydro-benzofuran-3-carbonsaeure-<2-diisopropylamino-aethylester> 95439-50-2 C23H29NO3
    3-Phenyl-2,3-dihydro-benzofuran-3-carbonsaeure-<2-diisopropylamino-aethylester>
    —— 17-methyl-5-hydroxy-16-oxo-10-nor-14α-4,5-epoxymorphinan 107290-36-8 C16H19NO3
    17-methyl-5-hydroxy-16-oxo-10-nor-14α-4,5-epoxymorphinan
    —— 1174720-04-7 C24H27NO3
    —— 1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-ol 1380698-17-8 C11H12O2
    1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-ol
    —— Sodium 5-(N-methyl-N-propylsulfamoyl)-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate 103969-28-4 C13H14Cl2NO5S*Na
    Sodium 5-(N-methyl-N-propylsulfamoyl)-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate
    —— (2S,3R)-3-((R)-1-hydroxybutyl)-4,6-dimethoxy-2,3-dihydrobenzofuran-2-ol 1356485-69-2 C14H20O5
    (2S,3R)-3-((R)-1-hydroxybutyl)-4,6-dimethoxy-2,3-dihydrobenzofuran-2-ol
    —— 3-amino-N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)thieno[2,3-b]pyridine-2-carboxamide 1048960-00-4 C25H30N4O2S
    3-amino-N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)thieno[2,3-b]pyridine-2-carboxamide
    —— 2,3,3a,8a-tetrahydro-2-oxo-4-benzyloxy-6-hydroxy-furo<2,3-b>benzofuran 134836-36-5 C17H14O5
    2,3,3a,8a-tetrahydro-2-oxo-4-benzyloxy-6-hydroxy-furo<2,3-b>benzofuran
    —— 2',3',4,5,9',10'-hexamethoxyspiro(cyclohexa-3,5-diene-1,6'-dibenzo-<d,f><1,3>dioxepin)-2-one 85969-38-6 C24H24O9
    2',3',4,5,9',10'-hexamethoxyspiro(cyclohexa-3,5-diene-1,6'-dibenzo-<d,f><1,3>dioxepin)-2-one
    —— Acetic acid 5-amino-6,7-dichloro-2,3-dihydro-benzofuran-2-ylmethyl ester 113730-04-4 C11H11Cl2NO3
    Acetic acid 5-amino-6,7-dichloro-2,3-dihydro-benzofuran-2-ylmethyl ester
    —— 1093087-30-9 C16H22BrNO3*ClH
    —— 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)-N-methylacetamide 1452478-23-7 C18H17Cl2NO3
    2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)-N-methylacetamide
    —— 7-amino-5-chloro-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran 153880-25-2 C12H16ClNO
    7-amino-5-chloro-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran
    —— 2,3-dihydro-2-(iodomethyl)-7-isopropyl-2,4,6-trimethyl-5-benzofuranamine 204065-33-8 C15H22INO
    2,3-dihydro-2-(iodomethyl)-7-isopropyl-2,4,6-trimethyl-5-benzofuranamine
    —— Aethyl-2,3-dihydro-5-hydroxybenzofuran-2-carboxylat 34701-80-9 C11H12O4
    Aethyl-2,3-dihydro-5-hydroxybenzofuran-2-carboxylat
    —— 2-methyl-2-(3-(triisopropylsilyl)prop-2-ynyl)-2,3-dihydro-1-benzofuran-5-carbonitrile 1203447-34-0 C22H31NOSi
    2-methyl-2-(3-(triisopropylsilyl)prop-2-ynyl)-2,3-dihydro-1-benzofuran-5-carbonitrile
    —— 6,7-dichloro-5-(N-ethyl-N-methylsulfamoyl)-2,3-dihydrobenzofuran-2-carboxylic acid 103969-27-3 C12H12Cl2NO5S*Na
    6,7-dichloro-5-(N-ethyl-N-methylsulfamoyl)-2,3-dihydrobenzofuran-2-carboxylic acid
    —— 5-bromo-2-methylidene-3H-1-benzofuran-3-ol 1384475-81-3 C9H7BrO2
    5-bromo-2-methylidene-3H-1-benzofuran-3-ol
    —— methyl 4-(4-(2-(1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yl)-2-methyl-2,3-dihydrobenzofuran-5-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butanoate 1346529-82-5 C31H40N4O5S
    methyl 4-(4-(2-(1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yl)-2-methyl-2,3-dihydrobenzofuran-5-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butanoate
    —— 3,3a-dihydroxy-4,6-bis(benzyloxy)-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran 78596-85-7 C24H22O6
    3,3a-dihydroxy-4,6-bis(benzyloxy)-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran
    —— 6,7-dichloro-4-nitro-2,3-dihydrobenzofuran-2-carboxylic acid 113730-50-0 C9H5Cl2NO5
    6,7-dichloro-4-nitro-2,3-dihydrobenzofuran-2-carboxylic acid
    —— (1S,2R,3aS,9aR)-1-Allyl-5-methoxy-2-methoxymethoxy-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxine 120888-19-9 C17H22O5
    (1S,2R,3aS,9aR)-1-Allyl-5-methoxy-2-methoxymethoxy-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxine
    —— Acetic acid 5-(benzyl-methyl-sulfamoyl)-6,7-dichloro-2,3-dihydro-benzofuran-2-ylmethyl ester 103969-31-9 C19H19Cl2NO5S
    Acetic acid 5-(benzyl-methyl-sulfamoyl)-6,7-dichloro-2,3-dihydro-benzofuran-2-ylmethyl ester
    —— 1-(benzyloxy)-3-(2,3-dihydrobenzofuran-7-yl)urea 1400979-87-4 C16H16N2O3
    1-(benzyloxy)-3-(2,3-dihydrobenzofuran-7-yl)urea
    —— ethyl (2Z)-2-[(4-chlorophenyl)sulfonylmethylidene]-4-hydroxy-7-methyl-3H-chromene-4-carboxylate 1380745-92-5 C20H19ClO6S
    ethyl (2Z)-2-[(4-chlorophenyl)sulfonylmethylidene]-4-hydroxy-7-methyl-3H-chromene-4-carboxylate
    —— (+)-2-isopropyl-5-methyl-2,3-dihydrobenzofuran-4-ol 581096-43-7 C12H16O2
    (+)-2-isopropyl-5-methyl-2,3-dihydrobenzofuran-4-ol
    —— N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-1,3-benzothiazole-2-carboxamide 1048959-42-7 C25H29N3O2S
    N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-1,3-benzothiazole-2-carboxamide
    —— 6,6'-dibromo-3,3'-dimethyl-2,2'-spirobi[chroman] 1383125-45-8 C19H18Br2O2
    6,6'-dibromo-3,3'-dimethyl-2,2'-spirobi[chroman]
    —— 3-Hydroxymethyl-2,3-dihydro-benzofuran-4-carboxylic acid diethylamide 93280-65-0 C14H19NO3
    3-Hydroxymethyl-2,3-dihydro-benzofuran-4-carboxylic acid diethylamide
    —— (4aSR,9RS,9aSR)-9-(nitromethyl)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-5-ol 1393376-85-6 C14H17NO4
    (4aSR,9RS,9aSR)-9-(nitromethyl)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-5-ol
    —— 6-Ethyl-3-methylene-4-phenyl-chroman-2-one 98061-76-8 C18H16O2
    6-Ethyl-3-methylene-4-phenyl-chroman-2-one