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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
    —— (+/-)-7-methyl-2-hydroxymethyl-2,3-dihydrobenzofuran 312608-55-2 C10H12O2
    (+/-)-7-methyl-2-hydroxymethyl-2,3-dihydrobenzofuran
    —— (E)-5-Methoxy-2-(4-methoxy-2,3,3-trimethyl-2,3-dihydro-benzofuran-6-yl)-3-oxo-hex-4-enoic acid methyl ester 104875-32-3 C20H26O6
    (E)-5-Methoxy-2-(4-methoxy-2,3,3-trimethyl-2,3-dihydro-benzofuran-6-yl)-3-oxo-hex-4-enoic acid methyl ester
    —— methyl 6-(2,3-dihydro-4-methoxy-2,3,3-trimethylbenzofuranyl)acetate 104875-30-1 C15H20O4
    methyl 6-(2,3-dihydro-4-methoxy-2,3,3-trimethylbenzofuranyl)acetate
    —— methyl 6-(7-carbomethoxy-2,3-dihydro-4-hydroxy-2,3,3,-trimethylbenzofuranyl)acetate 104875-27-6 C16H20O6
    methyl 6-(7-carbomethoxy-2,3-dihydro-4-hydroxy-2,3,3,-trimethylbenzofuranyl)acetate
    —— 1-[(5-bromo-2,3-dihydro-2,2-dimethyl-benzofuran-7-yl)-oxy]-4-[4-methyl-piperidin-1-yl]-butane 1089758-67-7 C20H30BrNO2
    1-[(5-bromo-2,3-dihydro-2,2-dimethyl-benzofuran-7-yl)-oxy]-4-[4-methyl-piperidin-1-yl]-butane
    —— Oxime of 1'-(4-nitrophenyl)-spiro(naphthalene-1(2H),2'(1'H)-naphtho<2,1-b>furan)-2-one 146307-45-1 C27H18N2O4
    Oxime of 1'-(4-nitrophenyl)-spiro(naphthalene-1(2H),2'(1'H)-naphtho<2,1-b>furan)-2-one
    —— 2-(N-methyl-N-propionyl)amino-5-hydroxy-methyl-3-(2',5'-dihydroxy)phenyl-2,3-dihydrobenzofurane 82334-16-5 C19H21NO5
    2-(N-methyl-N-propionyl)amino-5-hydroxy-methyl-3-(2',5'-dihydroxy)phenyl-2,3-dihydrobenzofurane
    —— 1-(5-fluoro-2,3-dihydro-benzofuran-3-yl)-3-(2-hydroxy-ethyl)-thiourea 1084899-11-5 C11H13FN2O2S
    1-(5-fluoro-2,3-dihydro-benzofuran-3-yl)-3-(2-hydroxy-ethyl)-thiourea
    —— 3a,8b-dihydro-3H-benzofuro<3,2-c>pyrazole 133625-61-3 C9H8N2O
    3a,8b-dihydro-3H-benzofuro<3,2-c>pyrazole
    —— 3-(6-Benzyloxy-4,7-dimethoxy-2,3-dihydro-benzofuran-5-yl)-propionic acid 3-methyl-but-2-enyl ester 147914-52-1 C25H30O6
    3-(6-Benzyloxy-4,7-dimethoxy-2,3-dihydro-benzofuran-5-yl)-propionic acid 3-methyl-but-2-enyl ester
    —— 3-hydroxy-3-[2-(morpholin-4-yl)-4-(trifluoromethyl)pyrimidin-5-yl]-2,3-dihydro-1-benzofuran-2-carboxylic acid 1198468-78-8 C18H16F3N3O5
    3-hydroxy-3-[2-(morpholin-4-yl)-4-(trifluoromethyl)pyrimidin-5-yl]-2,3-dihydro-1-benzofuran-2-carboxylic acid
    —— (2R,3aS,8bS)-8-Ethyl-2,3,3a,8b-tetrahydro-benzo[b]furo[2,3-d]furan-2-carbonitrile 909532-81-6 C13H13NO2
    (2R,3aS,8bS)-8-Ethyl-2,3,3a,8b-tetrahydro-benzo[b]furo[2,3-d]furan-2-carbonitrile
    —— [4-(Ethoxycarbonyl)-2,3-dihydrobenzo[d]furan-2-yl]methyl Acetate 532399-75-0 C14H16O5
    [4-(Ethoxycarbonyl)-2,3-dihydrobenzo[d]furan-2-yl]methyl Acetate
    —— (-)-3-(4-trifluoromethyl-phenyl)-2,3-dihydro-benzofuran-3-ol —— C15H11F3O2
    (-)-3-(4-trifluoromethyl-phenyl)-2,3-dihydro-benzofuran-3-ol
    —— 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol 923595-24-8 C15H14O2
    5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol
    —— methyl (2R*,3S*)-<3-(2-hydroxyethyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>acetate 126666-11-3 C16H20O5
    methyl (2R*,3S*)-<3-(2-hydroxyethyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>acetate
    —— (RS)-2-bromomethyl-2,3-dihydro-benzofuran-5-ylamine 208842-46-0 C9H10BrNO
    (RS)-2-bromomethyl-2,3-dihydro-benzofuran-5-ylamine
    —— 5-hydroxy-4-nitro-2-(2-oxoethyl)-2,3-dihydrobenzo[b]furan 130663-60-4 C10H9NO5
    5-hydroxy-4-nitro-2-(2-oxoethyl)-2,3-dihydrobenzo[b]furan
    —— 4-(Diethylcarbamoyl)-2-methyl-2,3-dihydrobenzo<b>furan 88440-88-4 C14H19NO2
    4-(Diethylcarbamoyl)-2-methyl-2,3-dihydrobenzo<b>furan
    —— 6-(2-methyl-2,3-dihydro-benzofuran-5-yl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 861850-99-9 C13H12N2O2S
    6-(2-methyl-2,3-dihydro-benzofuran-5-yl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
    —— 5-chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran 91681-28-6 C13H16ClNO2
    5-chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran
    —— 5-chloro-2-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran 91681-31-1 C13H16ClNO2
    5-chloro-2-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran
    —— 3-(5-bromo-2,3-dihydrobenzofuran-7-sulfonylamino)thiophene-2-carboxylic acid methyl ester 1268618-42-3 C14H12BrNO5S2
    3-(5-bromo-2,3-dihydrobenzofuran-7-sulfonylamino)thiophene-2-carboxylic acid methyl ester
    —— 3-(5-bromo-2,3-dihydrobenzofuran-7-sulfonylamino)thiophene-2-carboxylic acid 1268618-43-4 C13H10BrNO5S2
    3-(5-bromo-2,3-dihydrobenzofuran-7-sulfonylamino)thiophene-2-carboxylic acid
    —— (E)-3-(2,2-diethoxyethylidene)-2,3-dihydrobenzofuran 1012872-48-8 C14H18O3
    (E)-3-(2,2-diethoxyethylidene)-2,3-dihydrobenzofuran
    —— (Z)-2-(2-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol 1008105-85-8 C16H14O3
    (Z)-2-(2-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol
    —— 2-(5-Chloro-2,3-dihydro-2-oxo-3-phenyl-3-benzofuranyl)acetic acid ethyl ester 118709-06-1 C18H15ClO4
    2-(5-Chloro-2,3-dihydro-2-oxo-3-phenyl-3-benzofuranyl)acetic acid ethyl ester
    —— 2-ethyl-2,2a,3,4,5,6-hexahydrocyclohepta<cd>benzofuran-2a-ol 176045-22-0 C14H18O2
    2-ethyl-2,2a,3,4,5,6-hexahydrocyclohepta<cd>benzofuran-2a-ol
    —— 2-isopropyl-2,2a,3,4,5,6-hexahydrocyclohepta<cd>benzofuran-2a-ol 176045-23-1 C15H20O2
    2-isopropyl-2,2a,3,4,5,6-hexahydrocyclohepta<cd>benzofuran-2a-ol
    —— 2-methyl-2,2a,3,4,5,6-hexahydrocyclohepta<cd>benzofuran-2a-ol 176045-21-9 C13H16O2
    2-methyl-2,2a,3,4,5,6-hexahydrocyclohepta<cd>benzofuran-2a-ol
    —— 2,2,4,6-Tetramethyl-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester 82366-92-5 C14H18O3
    2,2,4,6-Tetramethyl-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester
    —— 2,2,4,6,7-Pentamethyl-3-(4-propylphenyl)-2,3-dihydrobenzofuran 142874-63-3 C22H28O
    2,2,4,6,7-Pentamethyl-3-(4-propylphenyl)-2,3-dihydrobenzofuran
    —— 3-(4-fluorophenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine 142873-26-5 C19H22FNO
    3-(4-fluorophenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine
    —— 2,2,4,6,7-Pentamethyl-3-(4-pentylphenyl)-2,3-dihydrobenzofuran 142874-64-4 C24H32O
    2,2,4,6,7-Pentamethyl-3-(4-pentylphenyl)-2,3-dihydrobenzofuran
    —— 2,2,4,6,7-Pentamethyl-5-nitro-3-(4-propylphenyl)-2,3-dihydrobenzofuran 142874-72-4 C22H27NO3
    2,2,4,6,7-Pentamethyl-5-nitro-3-(4-propylphenyl)-2,3-dihydrobenzofuran
    —— 3-(4-Fluorophenyl)-2,2,4,6,7-pentamethyl-5-nitro-2,3-dihydrobenzofuran 142874-70-2 C19H20FNO3
    3-(4-Fluorophenyl)-2,2,4,6,7-pentamethyl-5-nitro-2,3-dihydrobenzofuran
    —— 2,2,4,6,7-Pentamethyl-5-nitro-3-(4-pentylphenyl)-2,3-dihydrobenzofuran 142874-73-5 C24H31NO3
    2,2,4,6,7-Pentamethyl-5-nitro-3-(4-pentylphenyl)-2,3-dihydrobenzofuran
    —— 2,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran 142874-69-9 C19H21NO3
    2,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran
    —— 3-(4-Fluorophenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran 142874-61-1 C19H21FO
    3-(4-Fluorophenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran
    —— (+/-)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}propan-2-amine 852122-28-2 C20H24ClNO
    (+/-)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}propan-2-amine
    —— (+/-)-4-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}thiomorpholine 852122-32-8 C21H24ClNOS
    (+/-)-4-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}thiomorpholine
    —— (+/-)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}pyrrolidine 852122-35-1 C21H24ClNO
    (+/-)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}pyrrolidine
    —— (+/-)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine 852125-54-3 C18H20ClNO
    (+/-)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine
    —— (+/-)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}piperidine 852122-30-6 C22H26ClNO
    (+/-)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}piperidine
    —— (+/-)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}ethanamine 852122-27-1 C19H22ClNO
    (+/-)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}ethanamine
    —— (+/-)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}propan-1-amine 852122-33-9 C20H24ClNO
    (+/-)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}propan-1-amine
    —— (+/-)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}piperazine 852122-34-0 C21H25ClN2O
    (+/-)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}piperazine
    —— (+/-)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}dimethylamine 852122-29-3 C19H22ClNO
    (+/-)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}dimethylamine
    —— (+/-)-4-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}morpholine 852122-31-7 C21H24ClNO2
    (+/-)-4-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}morpholine
    —— (R)-1-((2S,3S)-3-(benzylamino)-4,6-dimethoxy-2,3-dihydrobenzofuran-2-yl)butan-1-ol 1356485-55-6 C21H27NO4
    (R)-1-((2S,3S)-3-(benzylamino)-4,6-dimethoxy-2,3-dihydrobenzofuran-2-yl)butan-1-ol