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。
中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
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—— | (3S)-3-[(3S)-3-(4-chlorophenyl)-2-oxo-1-benzofuran-3-yl]-1-phenylpyrrolidine-2,5-dione | 1258326-26-9 | C24H16ClNO4 |
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—— | (3S)-3-[(3S)-7-methoxy-2-oxo-3-phenyl-1-benzofuran-3-yl]-1-phenylpyrrolidine-2,5-dione | 1258326-25-8 | C25H19NO5 |
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—— | (3S)-3-[(3S)-5-chloro-2-oxo-3-phenyl-1-benzofuran-3-yl]-1-phenylpyrrolidine-2,5-dione | 1258326-24-7 | C24H16ClNO4 |
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—— | 6,7-Dimethyl-2,3-dihydro-1-benzofuran-3-amine hydrochloride | 1258649-70-5 | C10H14ClNO |
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—— | 2,3-dihydro-α,α-dimethyl-5-benzofuranmethanol | 82954-97-0 | C11H14O2 |
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—— | 5-Fluoro-2,3-dihydro-benzofuran-3-ylamine hydrochloride | 1187927-83-8 | C8H9ClFNO |
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—— | sodium;4-[(2R,3aS,8bS)-2-hydroxy-1-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoate | 88475-69-8 | C24H29NaO5 |
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—— | 2-(Prop-1-en-1-yl)-2,3-dihydro-1-benzofuran | 132067-60-8 | C11H12O |
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—— | trans-3-carboxymethyl-2-vinyl-2,3-dihydrobenzo[b]furan | 113982-25-5 | C12H12O3 |
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—— | 6-[(6-Methoxy-3,7,7-trimethyloct-2-en-1-yl)oxy]-2,3-dihydro-1-benzofuran | 51079-81-3 | C20H30O3 |
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—— | 6-[(2,3-Dihydro-1-benzofuran-6-yl)oxy]-4-methylhex-4-enal | 51079-82-4 | C15H18O3 |
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—— | (cis)-2-(2,3-Dihydro-2,2-dimethyl-7-methoxybenzofuran-4-carbonyl)-1,2,3,6-tetrahydro-benzoic Acid | 474001-89-3 | C19H22O5 |
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—— | 5-methoxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-carboxylic acid | 183142-35-0 | C15H20O4 |
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—— | (3,4,4-trifluoro-3-butenyl) N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yl)dithiocarbamate | 115070-47-8 | C15H16F3NOS2 |
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—— | 6-[(7-Methoxy-3,7-dimethylnon-2-en-1-yl)oxy]-2,3-dihydro-1-benzofuran | 51079-76-6 | C20H30O3 |
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—— | 4-(5,6,7-Trimethyl-2,3-dihydro-1-benzofuran-4-yl)but-3-en-2-one | 89240-33-5 | C15H18O2 |
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—— | 6-[(6-Methyloct-5-en-2-yl)oxy]-2,3-dihydro-1-benzofuran | 51079-74-4 | C17H24O2 |
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—— | 1-(2,3-Dihydro-4,5,6-trimethylbenzo[b]furan-7-yl)but-1-en-3-one | 89240-14-2 | C15H18O2 |
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—— | 6-[(3,7,7-Trimethylocta-2,4-dien-1-YL)oxy]-2,3-dihydro-1-benzofuran | 51079-53-9 | C19H26O2 |
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—— | 5-Carboxy-2,3-dihydro-2-hydroxy-alpha,alpha,3,3-tetramethyl-7-benzofuranacetic acid | 67565-96-2 | C15H18O6 |
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—— | 2-[4-[5-(1-propylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-2,3-dihydro-1-benzofuran-2-yl]piperidin-1-yl]-5-(trifluoromethyl)pyrimidine | 1346529-31-4 | C26H31F3N4O3S |
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—— | 4-[[4-[4,7-difluoro-2-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-5-yl]-3,6-dihydro-2H-pyridin-1-yl]sulfonyl]-2-methylbutan-2-ol | 1346529-52-9 | C30H40F2N4O4S |
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—— | 5-chloro-2-[4-[5-(1-propylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-2,3-dihydro-1-benzofuran-2-yl]piperidin-1-yl]pyrimidine | 1346529-36-9 | C25H31ClN4O3S |
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—— | N,N-Dimethyl-2,3-dihydro-benzofuran-2-carboxamid | 17349-65-4 | C11H13NO2 |
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—— | 5-Benzofurancarboxamide, N-(2-cyanopropyl)-2,3-dihydro- | 1270914-59-4 | C13H14N2O2 |
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—— | Ethyl Imicro-amino-2,3-dihydro-2-methyl-5-benzofuranhexanoate | 1183443-46-0 | C17H25NO3 |
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—— | 1-(2,3-Dihydro-1-benzofuran-5-yl)-2-(dimethylamino)ethan-1-one | 111038-60-9 | C12H15NO2 |
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—— | 5-Nitro-2,3-dihydro-1-benzofuran-3-amine | 944899-90-5 | C8H8N2O3 |
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—— | 1,2,3,4,4a,9a-Hexahydrobenzofuro[2,3-c]pyridine | 6783-76-2 | C11H13NO |
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—— | 3-[[[(2,3-Dihydro-5-benzofuranyl)methyl]amino]methyl]benzonitrile | 1178353-76-8 | C17H16N2O |
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—— | (I+/-R)-I+/--Ethenyl-2,3-dihydro-5-benzofuranmethanamine | 1212887-15-4 | C11H13NO |
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—— | N-[(5-Chloro-2-methoxyphenyl)methyl]-2,3-dihydro-2-benzofuranmethanamine | 1178365-60-0 | C17H18ClNO2 |
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—— | 2,3-Dihydro-3-[[1-(3-methoxyphenyl)ethyl]amino]-6-benzofuranol | 1183538-55-7 | C17H19NO3 |
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—— | 5-Benzofurancarboxamide, N-(2-amino-1-methyl-2-thioxoethyl)-2,3-dihydro-N-methyl- | 1458651-93-8 | C13H16N2O2S |
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—— | 6,11-Dioxa-3-thia-2,4,7,10-tetraazadodeca-7,9-dienoic acid, 8-((dimethylamino)carbonyl)-5-oxo-2,4,9-trimethyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester | 90293-54-2 | C21H29N5O7S |
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—— | (Z)-5-bromo-2-(4-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol | 1321849-10-8 | C16H13BrO3 |
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—— | (Z)-2-benzylidene-7-nitro-5-tert-butyl-2,3-dihydrobenzofuran-3-ol | 1262020-39-2 | C19H19NO4 |
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—— | (3S)-3-(4-chlorophenyl)-3-[(1R)-2-nitro-1-phenylethyl]-1-benzofuran-2-one | 1352953-60-6 | C22H16ClNO4 |
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—— | (3S)-5-chloro-3-[(1R)-2-nitro-1-phenylethyl]-3-phenyl-1-benzofuran-2-one | 1352953-58-2 | C22H16ClNO4 |
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—— | (1R,3aS,8bS)-5-(4-hydroxybutyl)-1-(2-methylprop-1-enyl)-3,3a-dihydro-1Hbenzo[b]cyclopenta[d]furan-2(8bH)-one | 1352145-67-5 | C19H24O3 |
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—— | (2-(2,3-Dihydrobenzofuran-5-yl)cyclopropyl)methanamine | 1269528-72-4 | C12H15NO |
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—— | 2-(6-Methoxy-2,3-dihydro-1-benzofuran-3-yl)acetic acid | 93198-72-2 | C11H12O4 |
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—— | (2R,2'R)-[(4aR,9bR)-6-methoxy-1,4,4a,9b-tetrahydrodibenzo-[b,d]furan-4a,9b-diyl]bis(methylene)bis(2-methoxy-2-phenylacetate) | 1374412-01-7 | C33H34O8 |
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—— | 3-tert-Butyl-5a,6,7,8-tetrahydrodibenzo[b,d]furan-2-ol | 893752-13-1 | C16H20O2 |
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—— | 4-(2-Nitroethenyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran | 178557-15-8 | C12H11NO4 |
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—— | (3R)-3-[2,2-bis(benzenesulfonyl)ethyl]-3-(4-chlorophenyl)-5-ethyl-1-benzofuran-2-one | 1374605-31-8 | C30H25ClO6S2 |
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—— | (3R)-3-[2,2-bis(benzenesulfonyl)ethyl]-3-(4-chlorophenyl)-5-methyl-1-benzofuran-2-one | 1374605-30-7 | C29H23ClO6S2 |
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—— | (3R)-3-[2,2-bis(benzenesulfonyl)ethyl]-7-ethyl-3-phenyl-1-benzofuran-2-one | 1374605-35-2 | C30H26O6S2 |
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—— | (3R)-3-[2,2-bis(benzenesulfonyl)ethyl]-3-phenyl-7-propan-2-yl-1-benzofuran-2-one | 1374605-36-3 | C31H28O6S2 |
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—— | (3R)-3-[2,2-bis(benzenesulfonyl)ethyl]-7-(2-methylpropyl)-3-phenyl-1-benzofuran-2-one | 1374605-37-4 | C32H30O6S2 |
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