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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
    —— bis<2-(5-chloro-2,3-dihydrobenzofuranyl)methyl>tellurium dichloride 78733-67-2 C18H16Cl4O2Te
    bis<2-(5-chloro-2,3-dihydrobenzofuranyl)methyl>tellurium dichloride
    —— (Z)-2-methyl-3-phenyl-3-hydroxy-2,3-dihydrobenzofuran 127154-59-0 C15H14O2
    (Z)-2-methyl-3-phenyl-3-hydroxy-2,3-dihydrobenzofuran
    —— nordeoxynivalenol B 103776-39-2 C14H18O5
    nordeoxynivalenol B
    —— 3-methyl-2,3-dihydrobenzofuran-5-sulfonyl chloride 869885-61-0 C9H9ClO3S
    3-methyl-2,3-dihydrobenzofuran-5-sulfonyl chloride
    —— Diethyl 2,9-dichloro-10b,10c-dihydrodibenzo[d,d']cyclobuta[1,2-b:4,3-b']difuran-5a,5b-dicarboxylate 67194-00-7 C22H18Cl2O6
    Diethyl 2,9-dichloro-10b,10c-dihydrodibenzo[d,d']cyclobuta[1,2-b:4,3-b']difuran-5a,5b-dicarboxylate
    —— 5,7-dimethyl-2-(phenylthiomethyl)-2,3-dihydrobenzofuran 126707-90-2 C17H18OS
    5,7-dimethyl-2-(phenylthiomethyl)-2,3-dihydrobenzofuran
    —— 5-Methoxy-2,3-dihydro-benzofuran-3-ylamine 109926-36-5 C9H11NO2
    5-Methoxy-2,3-dihydro-benzofuran-3-ylamine
    —— ethyl 2-acetyl-5-chloro-3-hydroxy-2,3-dihydrobenzofuran-2-carboxylate 1351932-18-7 C13H14O5
    ethyl 2-acetyl-5-chloro-3-hydroxy-2,3-dihydrobenzofuran-2-carboxylate
    —— 5-bromo-3-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran 1202504-23-1 C14H9BrCl2O
    5-bromo-3-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran
    —— 5-bromo-3-(2,4-dichlorophenyl)-1-benzofuran-2(3H)-one 1202504-21-9 C14H7BrCl2O2
    5-bromo-3-(2,4-dichlorophenyl)-1-benzofuran-2(3H)-one
    —— 5-Hydroxy-3,6-dimethyl-2,3-dihydrobenzofuran 111950-57-3 C10H12O2
    5-Hydroxy-3,6-dimethyl-2,3-dihydrobenzofuran
    —— cis(3a,8a)-4-hydroxy-2,3,3a,8a-tetrahydro-furanobenzofuran 135365-43-4 C10H10O3
    cis(3a,8a)-4-hydroxy-2,3,3a,8a-tetrahydro-furanobenzofuran
    —— 3-(4-chloro-2,3-dihydro-2,2-dimethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil 164915-52-0 C16H13ClF4N2O3
    3-(4-chloro-2,3-dihydro-2,2-dimethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil
    —— (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine 241136-29-8 C20H32N2O3S
    (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine
    —— 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol 913003-07-3 C23H28F3NO2
    4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol
    —— 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-(2R)-2-pentanol 913003-08-4 C23H28F3NO2
    4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-(2R)-2-pentanol
    —— 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-(2S)-2-pentanol 913003-09-5 C23H28F3NO2
    4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-(2S)-2-pentanol
    —— methyl 7-chloro-2,3-dihydro-6-methoxybenzofuran-2-carboxylate 90246-85-8 C11H11ClO4
    methyl 7-chloro-2,3-dihydro-6-methoxybenzofuran-2-carboxylate
    —— 1,4-Dichlor-3-hydroxy-8a-morpholin-4-yl-5,6,7,8a-tetrahydro-<4bH>-dibenzo<b,d>furan-8-on 150786-25-7 C16H17Cl2NO4
    1,4-Dichlor-3-hydroxy-8a-morpholin-4-yl-5,6,7,8a-tetrahydro-<4bH>-dibenzo<b,d>furan-8-on
    —— (2R*,3S*)-<3-(2-chloroethyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>ethanal 126666-13-5 C15H17ClO3
    (2R*,3S*)-<3-(2-chloroethyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>ethanal
    —— methyl (2R*,3S*)-<3-(3,5-dioxahexyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>acetate 126666-07-7 C18H24O6
    methyl (2R*,3S*)-<3-(3,5-dioxahexyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>acetate
    —— 6-methyl-2-oxa-3,4-benzobicyclo<3.2.0>heptan-7-one 99477-32-4 C11H10O2
    6-methyl-2-oxa-3,4-benzobicyclo<3.2.0>heptan-7-one
    —— 1-[3-Acetyl-6-hydroxy-4-(4-methoxy-phenyl)-1-methyl-1,9a-dihydro-4H-benzo[4,5]furo[2,3-b]pyridin-4a-yl]-ethanone 212623-31-9 C23H23NO5
    1-[3-Acetyl-6-hydroxy-4-(4-methoxy-phenyl)-1-methyl-1,9a-dihydro-4H-benzo[4,5]furo[2,3-b]pyridin-4a-yl]-ethanone
    —— 1-[3-Acetyl-6-hydroxy-4-(4-methoxy-phenyl)-1,9a-dihydro-4H-benzo[4,5]furo[2,3-b]pyridin-4a-yl]-ethanone 212623-30-8 C22H21NO5
    1-[3-Acetyl-6-hydroxy-4-(4-methoxy-phenyl)-1,9a-dihydro-4H-benzo[4,5]furo[2,3-b]pyridin-4a-yl]-ethanone
    —— 2-(2,2-dimethyl-2,3-Dihydrobenzofuran-7-yloxy)pyridin-3-amine 861673-97-4 C15H16N2O2
    2-(2,2-dimethyl-2,3-Dihydrobenzofuran-7-yloxy)pyridin-3-amine
    —— Carbamic acid, trithiobis(methyl-, bis(2,3-dihydro-2,2-dimethyl-7-benzofuranyl) ester 78081-80-8 C24H28N2O6S3
    Carbamic acid, trithiobis(methyl-, bis(2,3-dihydro-2,2-dimethyl-7-benzofuranyl) ester
    —— 2-(2',3'-dihydro-2'-ethylbenzo[b]furan-2'-yl)-5-methylsulfanyl-[1,3,4]oxadiazole 1041186-95-1 C13H14N2O2S
    2-(2',3'-dihydro-2'-ethylbenzo[b]furan-2'-yl)-5-methylsulfanyl-[1,3,4]oxadiazole
    —— 2-[5-(2',3'-dihydro-2'-ethylbenzo[b]furan-2'-yl)-[1,3,4]-oxadiazol-2-ylsulfanyl]acetic acid 1041186-98-4 C14H14N2O4S
    2-[5-(2',3'-dihydro-2'-ethylbenzo[b]furan-2'-yl)-[1,3,4]-oxadiazol-2-ylsulfanyl]acetic acid
    —— methyl 2-[5-(2',3'-dihydro-2'-ethylbenzo[b]furan-2'-yl)-[1,3,4]-oxadiazol-2-ylsulfanyl]acetate 1041186-97-3 C15H16N2O4S
    methyl 2-[5-(2',3'-dihydro-2'-ethylbenzo[b]furan-2'-yl)-[1,3,4]-oxadiazol-2-ylsulfanyl]acetate
    —— [(3R)-5-fluoro-2,3-dihydro-1-benzofuran-3-yl]methanol 502435-00-9 C9H9FO2
    [(3R)-5-fluoro-2,3-dihydro-1-benzofuran-3-yl]methanol
    —— 2,3-dihydro-2-(2-isopropenyl)-6-hydroxy-7-nitrobenzofuran 586963-74-8 C11H11NO4
    2,3-dihydro-2-(2-isopropenyl)-6-hydroxy-7-nitrobenzofuran
    —— N,N-bis(2-chloroethyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine 1243545-16-5 C17H25Cl2NO
    N,N-bis(2-chloroethyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine
    —— 2a,7b-Dihydro-7b-methyl-1,2-dioxeto<3,4-b>benzofuran 128753-83-3 C9H8O3
    2a,7b-Dihydro-7b-methyl-1,2-dioxeto<3,4-b>benzofuran
    —— 7-bromo-2,3-dihydro-1-benzofuran-3-amine hydrochloride 1258400-12-2 C8H8BrNO*ClH
    7-bromo-2,3-dihydro-1-benzofuran-3-amine hydrochloride
    —— 7-bromo-1-benzofuran-3(2H)-one O-methyloxime 1258400-10-0 C9H8BrNO2
    7-bromo-1-benzofuran-3(2H)-one O-methyloxime
    —— 5-fluoro-2-(methoxymethyl)-2,3-dihydrobenzofuran 1352740-33-0 C10H11FO2
    5-fluoro-2-(methoxymethyl)-2,3-dihydrobenzofuran
    —— ethyl (3-hydroxy-3-methyl-2,3-dihydro-2-benzo(b)furylidene)acetate 123368-75-2 C13H14O4
    ethyl (3-hydroxy-3-methyl-2,3-dihydro-2-benzo(b)furylidene)acetate
    —— ethyl (2S)-2,7-dimethyl-2,3-dihydrobenzofuran-2-carboxylate 1433062-29-3 C13H16O3
    ethyl (2S)-2,7-dimethyl-2,3-dihydrobenzofuran-2-carboxylate
    —— triisopropyl-[3-(5-bromo-2-methyl-2,3-dihydro-benzofuran-2-yl)-prop-1-ynyl]-silane 1203447-33-9 C21H31BrOSi
    triisopropyl-[3-(5-bromo-2-methyl-2,3-dihydro-benzofuran-2-yl)-prop-1-ynyl]-silane
    —— 1-[(3R)-3-(4-chlorophenyl)-2,3-dihydro-2-oxo-3-benzofuranyl]-1,2-hydrazinedicarboxylic acid,1,2-bis(phenylmethyl) ester 1314114-33-4 C30H23ClN2O6
    1-[(3R)-3-(4-chlorophenyl)-2,3-dihydro-2-oxo-3-benzofuranyl]-1,2-hydrazinedicarboxylic acid,1,2-bis(phenylmethyl) ester
    —— 2-(5-fluoro-2-methyl-2,3-dihydrobenzofuran-2-yl)acetonitrile 1372769-14-6 C11H10FNO
    2-(5-fluoro-2-methyl-2,3-dihydrobenzofuran-2-yl)acetonitrile
    —— 2-(4-chlorobenzyl)-6-(2,3-dihydro-1-benzofuran-5-yl)-4-hydroxymethyl-2H-pyridazin-3-one 756836-48-3 C20H17ClN2O3
    2-(4-chlorobenzyl)-6-(2,3-dihydro-1-benzofuran-5-yl)-4-hydroxymethyl-2H-pyridazin-3-one
    —— N-Acetylcarbofuran 15938-36-0 C14H17NO4
    N-Acetylcarbofuran
    —— 4aR,9aS,2'R-(+)-cis-2-(2'-hydroxy-2'-phenylethyl)-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol 1182348-83-9 C21H25NO3
    4aR,9aS,2'R-(+)-cis-2-(2'-hydroxy-2'-phenylethyl)-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol
    —— 4aS,9aR,2'R-(-)-cis-2-(2'-hydroxy-2'-phenylethyl)-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol 1182348-92-0 C21H25NO3
    4aS,9aR,2'R-(-)-cis-2-(2'-hydroxy-2'-phenylethyl)-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol
    —— 2-[3-(4-Chloro-phenyl)-2-oxo-2,3-dihydro-benzofuran-5-yl]-propionic acid 77143-71-6 C17H13ClO4
    2-[3-(4-Chloro-phenyl)-2-oxo-2,3-dihydro-benzofuran-5-yl]-propionic acid
    —— 2-[3-(4-Chloro-phenyl)-2-oxo-2,3-dihydro-benzofuran-5-yl]-propionic acid methyl ester 77143-65-8 C18H15ClO4
    2-[3-(4-Chloro-phenyl)-2-oxo-2,3-dihydro-benzofuran-5-yl]-propionic acid methyl ester
    —— 2-(2-Oxo-3-phenyl-2,3-dihydro-benzofuran-5-yl)-propionic acid methyl ester 77143-64-7 C18H16O4
    2-(2-Oxo-3-phenyl-2,3-dihydro-benzofuran-5-yl)-propionic acid methyl ester
    —— 2-[3-(4-Bromo-phenyl)-2-oxo-2,3-dihydro-benzofuran-5-yl]-propionic acid methyl ester 77143-66-9 C18H15BrO4
    2-[3-(4-Bromo-phenyl)-2-oxo-2,3-dihydro-benzofuran-5-yl]-propionic acid methyl ester
    —— 2,3-Dihydro-benzofuran-2-carboxylic acid (2-diethylamino-ethyl)-amide 42973-03-5 C15H22N2O2
    2,3-Dihydro-benzofuran-2-carboxylic acid (2-diethylamino-ethyl)-amide