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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
    —— trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,6-dioxo-piperidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid 1443020-14-1 C33H42N2O7
    trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,6-dioxo-piperidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid
    —— 1174720-76-3 C20H24N2O2S
    —— 2,5,7-Trimethyl-2,3-dihydro-1-benzofuran-3-amine 1248090-43-8 C11H15NO
    2,5,7-Trimethyl-2,3-dihydro-1-benzofuran-3-amine
    —— 2,4,9,11-Tetrachloro-13-phenyl-6,7-dihydro-13H-5,8-dioxa-dibenzo[a,d]cyclononene 110422-81-6 C21H14Cl4O2
    2,4,9,11-Tetrachloro-13-phenyl-6,7-dihydro-13H-5,8-dioxa-dibenzo[a,d]cyclononene
    —— (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-N-(4-fluorobenzyl)-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide 925439-37-8 C24H20FNO7
    (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-N-(4-fluorobenzyl)-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide
    —— 1,2,3,4,4a,9b-Hexahydro-8-hydroxy-9a-methyl-3-oxo-dibenzofuran 91910-04-2 C13H14O3
    1,2,3,4,4a,9b-Hexahydro-8-hydroxy-9a-methyl-3-oxo-dibenzofuran
    —— (9aS)-8-acetyl-1,7-dihydroxy-N-(4-hydroxy-2,3,5,6-tetramethylbenzyl)-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide 925440-91-1 C28H29NO8
    (9aS)-8-acetyl-1,7-dihydroxy-N-(4-hydroxy-2,3,5,6-tetramethylbenzyl)-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide
    —— (+/-)-{[7-(2,6-dimethylphenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852125-50-9 C19H23NO2
    (+/-)-{[7-(2,6-dimethylphenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— 2,3-Dihydro-5,6-benzofurandiol 5-methoxymethyl ether 119795-14-1 C10H12O4
    2,3-Dihydro-5,6-benzofurandiol 5-methoxymethyl ether
    —— (+/-)-{[6-chloro-7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852123-99-0 C16H15Cl2NO
    (+/-)-{[6-chloro-7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— (+/-)-{[7-(4-fluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852124-80-2 C17H18FNO
    (+/-)-{[7-(4-fluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— 2,3-dihydro-benzofuran-7-carboxylic acid {(R)-3[5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carbonyl]-thiazolidin-4-ylmethyl}-amide 1061589-10-3 C24H22FN3O3S2
    2,3-dihydro-benzofuran-7-carboxylic acid {(R)-3[5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carbonyl]-thiazolidin-4-ylmethyl}-amide
    —— 5-methyl-2-(phenylthiomethyl)-2,3-dihydrobenzofuran 74455-33-7 C16H16OS
    5-methyl-2-(phenylthiomethyl)-2,3-dihydrobenzofuran
    —— (1R,2R,3R,4aR,9bS)-9b-(2-(dimethylamino)-2-oxoethyl)-1,2-dihydroxy-6-methoxy-1,2,3,4,4a,9b-hexahydrodibenzo[b,d]furan-3-yl acetate 1256603-65-2 C19H25NO7
    (1R,2R,3R,4aR,9bS)-9b-(2-(dimethylamino)-2-oxoethyl)-1,2-dihydroxy-6-methoxy-1,2,3,4,4a,9b-hexahydrodibenzo[b,d]furan-3-yl acetate
    —— 2-((5aS,6S,7S,8R,9R,9aS)-2,6-dibromo-7,8,9-trihydroxy-4-methoxy-6,7,8,9-tetrahydrodibenzo[b,d]furan-9a(5aH)-yl)-N,N-dimethylacetamide 1256603-60-7 C17H21Br2NO6
    2-((5aS,6S,7S,8R,9R,9aS)-2,6-dibromo-7,8,9-trihydroxy-4-methoxy-6,7,8,9-tetrahydrodibenzo[b,d]furan-9a(5aH)-yl)-N,N-dimethylacetamide
    —— 2-bromo-N-(2-methyl-2,3-dihydro-1-benzofuran-7-yl)hexanamide 113722-14-8 C15H20BrNO2
    2-bromo-N-(2-methyl-2,3-dihydro-1-benzofuran-7-yl)hexanamide
    —— [(2-ethyl-6,7-difluoro-2-methyl-3H-chromen-4-ylidene)amino]thiourea 1246537-71-2 C13H15F2N3OS
    [(2-ethyl-6,7-difluoro-2-methyl-3H-chromen-4-ylidene)amino]thiourea
    —— tert-butyl 9-(3-fluorophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate 1055880-78-8 C20H22FNO3
    tert-butyl 9-(3-fluorophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
    —— (R)-6,7-Dichloro-2-(dichloro-phenylsulfanyl-methyl)-2,3-dihydro-benzofuran 118166-42-0 C15H10Cl4OS
    (R)-6,7-Dichloro-2-(dichloro-phenylsulfanyl-methyl)-2,3-dihydro-benzofuran
    —— (2R)-5-Carboxy-2,3-dihydro-cumarilsaeure 90771-91-8 C10H8O5
    (2R)-5-Carboxy-2,3-dihydro-cumarilsaeure
    —— (+/-)-{[6-fluoro-7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852123-95-6 C16H15ClFNO
    (+/-)-{[6-fluoro-7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— (+/-)-{[7-(4-methylphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852124-78-8 C18H21NO
    (+/-)-{[7-(4-methylphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— (+/-)-{[5-isopropyl-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine 852122-61-3 C19H23NO
    (+/-)-{[5-isopropyl-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine
    —— (+/-)-{[5-chloro-7-(2,3-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852124-63-1 C18H20ClNO
    (+/-)-{[5-chloro-7-(2,3-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— {[(2R)-7-(4-chloro-2-methylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine 852282-19-0 C16H15ClFNO
    {[(2R)-7-(4-chloro-2-methylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine
    —— (+/-)-{[7-(2,6-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852124-88-0 C17H17Cl2NO
    (+/-)-{[7-(2,6-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— 3-<i>m</i>-tolyl-3<i>H</i>-benzofuran-2-one 65425-04-9 C15H12O2
    3-<i>m</i>-tolyl-3<i>H</i>-benzofuran-2-one
    —— (2S,3S)-2-Allyl-4-ethyl-2,3-dihydro-benzofuran-3-ol 82064-79-7 C13H16O2
    (2S,3S)-2-Allyl-4-ethyl-2,3-dihydro-benzofuran-3-ol
    —— (5a<i>S</i>)-9a-(2-dimethylamino-ethyl)-4-methoxy-9-oxo-(5a<i>r</i>,9a<i>c</i>)-5a,6,7,8,9,9a-hexahydro-dibenzofuran-1-carbaldehyde oxime 97438-09-0 C18H24N2O4
    (5a<i>S</i>)-9a-(2-dimethylamino-ethyl)-4-methoxy-9-oxo-(5a<i>r</i>,9a<i>c</i>)-5a,6,7,8,9,9a-hexahydro-dibenzofuran-1-carbaldehyde oxime
    —— 3-[[4-[2-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-5-yl]-3,6-dihydro-2H-pyridin-1-yl]sulfonyl]propan-1-ol 1346529-17-6 C28H38N4O4S
    3-[[4-[2-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-5-yl]-3,6-dihydro-2H-pyridin-1-yl]sulfonyl]propan-1-ol
    —— 6-hydroxy-3,4,4a,9a-tetrahydro-2H-benzofuro[2,3-b]pyran-5-carbaldehyde 1072895-48-7 C12H12O4
    6-hydroxy-3,4,4a,9a-tetrahydro-2H-benzofuro[2,3-b]pyran-5-carbaldehyde
    —— (4S,4aR,9bR)-9b-(2-Dimethylamino-ethyl)-6-fluoro-1,4,4a,9b-tetrahydro-dibenzofuran-4-ol 108275-22-5 C16H20FNO2
    (4S,4aR,9bR)-9b-(2-Dimethylamino-ethyl)-6-fluoro-1,4,4a,9b-tetrahydro-dibenzofuran-4-ol
    —— 2-Acetoxy-1-<(2RS,3RS)-2,3-dihydro-2,6-dimethoxy-1-benzofuran-3-yl>-2-methyl-1-propanon 91360-52-0 C16H20O6
    2-Acetoxy-1-<(2RS,3RS)-2,3-dihydro-2,6-dimethoxy-1-benzofuran-3-yl>-2-methyl-1-propanon
    —— methyl 5-[(2S)-2-({[(2S)-2-hydroxy-3-phenoxypropyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]-3-thiophenecarboxylate 437764-68-6 C25H27NO5S
    methyl 5-[(2S)-2-({[(2S)-2-hydroxy-3-phenoxypropyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]-3-thiophenecarboxylate
    —— (+/-)-2-(azidomethyl)-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran 1072073-34-7 C16H15N3O2
    (+/-)-2-(azidomethyl)-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran
    —— (+/-)-N-methyl-1-[7-(3-fluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine 852125-11-2 C17H15F4NO
    (+/-)-N-methyl-1-[7-(3-fluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
    —— 8-butyrylamino-6-methyl-3,4-dihydro-2H-benzo[b][1,5]oxazocin-3-ol 27827-68-5 C15H20N2O3
    8-butyrylamino-6-methyl-3,4-dihydro-2H-benzo[b][1,5]oxazocin-3-ol
    —— (S)-2-(2-methyl-2,3-dihydrobenzofuran-2-yl)propan-2-ol 1433066-16-0 C12H16O2
    (S)-2-(2-methyl-2,3-dihydrobenzofuran-2-yl)propan-2-ol
    —— trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-propyl]-{4-[3-(2,5-dioxo-pyrrolidin-1-yl)-propyl]-3-methoxy-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid 1443020-42-5 C34H44N2O6
    trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-propyl]-{4-[3-(2,5-dioxo-pyrrolidin-1-yl)-propyl]-3-methoxy-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid
    —— 2H,3H-3-((1-hydroxycyclopentyl)methyl)benzofuran 130013-32-0 C14H18O2
    2H,3H-3-((1-hydroxycyclopentyl)methyl)benzofuran
    —— (+/-)-{[5-ethyl-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine 852122-59-9 C18H21NO
    (+/-)-{[5-ethyl-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine
    —— allyl (2R,3S)-2-((4-bromobenzylamino)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate 1592908-64-9 C24H29BrN2O6
    allyl (2R,3S)-2-((4-bromobenzylamino)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate
    —— (+/-)-tert-butyl [(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methoxy]dimethylsilane 852110-48-6 C16H26O3Si
    (+/-)-tert-butyl [(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methoxy]dimethylsilane
    —— 389845-63-0 C18H20ClNO2
    —— trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{3-methoxy-4-[2-(3-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-ethoxy]-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid 1443020-35-6 C33H41N3O7
    trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{3-methoxy-4-[2-(3-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-ethoxy]-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid
    —— 6-(4-(tert-butyl)phenyl)-3,3-dimethylbenzofuran-2(3H)-one 1419174-43-8 C20H22O2
    6-(4-(tert-butyl)phenyl)-3,3-dimethylbenzofuran-2(3H)-one
    —— (+/-)-2-(azidomethyl)-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran 1072073-33-6 C17H17N3O
    (+/-)-2-(azidomethyl)-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran
    —— bis<2-(5-methyl-2,3-dihydrobenzofuranyl)methyl> ditelluride 78733-68-3 C20H22O2Te2
    bis<2-(5-methyl-2,3-dihydrobenzofuranyl)methyl> ditelluride
    —— methyl (2R*,3S*)-<3-(2-chloroethyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>acetate 126666-12-4 C16H19ClO4
    methyl (2R*,3S*)-<3-(2-chloroethyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>acetate
    —— 2,3-dihydro-3,3-dimethyl-2-methylcarbamoyloxybenzofuran-5-yldiethylaminosulfonate 57161-73-6 C16H24N2O6S
    2,3-dihydro-3,3-dimethyl-2-methylcarbamoyloxybenzofuran-5-yldiethylaminosulfonate