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 |
|---|---|---|---|
| —— | (S)-[(2R)-2,3-dihydro-1-benzofuran-2-yl]-[3,4,5-tris(phenylmethoxy)phenyl]methanol | 1131849-77-8 | C36H32O5 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(2,5-dioxopyrrolidin-1-yl)-acetamide | 1048960-02-6 | C23H31N3O4 |
| —— | Methyl 2,3-O,O'-(2-methoxycarbonylbenzyliden)-2,3-dihydroxybenzoat | 39600-98-1 | C17H14O6 |
| —— | (4aS,9bS)-8,9b-Dimethyl-3,4,4a,9b-tetrahydro-dibenzofuran | 89228-58-0 | C14H16O |
| —— | (1S,3S)-3-[([(R)-1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclopentanecarboxylic acid | 1443020-85-6 | C31H38N2O7 |
| —— | (S)-4-(2-methyl-2,3-dihydro-7-benzofuroyl)amino-1-methyl-3-propyl-5-pyrazolecarboxamide | 386714-02-9 | C18H22N4O3 |
| —— | 4,8-Dimethyl-chroman-4-ol | 104174-33-6 | C11H14O2 |
| —— | cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzo[b]furan | 72229-59-5 | C13H14O4 |
| —— | 8-bromo-2,3-dihydrobenzo[b][1,4]dioxine-2-carbonitrile | 1221072-51-0 | C9H6BrNO2 |
| —— | (2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile | 474418-76-3 | C20H31NO2Si |
| —— | 4-{5-[1-(2,3-Dihydro-1-benzofuran-5-sulfonyl)-4-fluoropyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl}pyridine | 2097936-46-2 | C19H17FN4O4S |
| —— | 3-methoxycatecholborane | 1228459-05-9 | C7H7BO3 |
| —— | 1602573-94-3 | C20H22BrN3O | |
| —— | 2-Methyl-4-o-tolyl-4H-benzo[h]chromen-4-ol | 135979-04-3 | C21H18O2 |
| —— | (+/-)-{[5-chloro-7-(2,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852125-52-1 | C16H14Cl3NO |
| —— | 2-acetoxymethyl-4,7-difluoro-2,3-dihydrobenzofuran | 196519-73-0 | C11H10F2O3 |
| —— | (5aS,7R,9aS)-7-[(tert-butyldimethylsilyl)oxy]-6,7-dihydro-4-methoxy-N-methyl-9a(5aH)-dibenzo-furanacetamide | 1268868-67-2 | C22H33NO4Si |
| —— | (1R,2R)-2-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclopropanecarboxylic acid | 1443020-88-9 | C29H34N2O7 |
| —— | 1619243-82-1 | C26H34N4O | |
| —— | 5-cyclopropyl-2-(4-(5-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)pyrimidine | 1602575-20-1 | C25H30N4O |
| —— | 2-[(2,3-dihydro-1-benzofuran-5-ylmethyl)sulfanyl]-5-hydroxypyrimidin-4(3H)-one | 1417817-32-3 | C13H12N2O3S |
| —— | 2-(4-(7-fluoro-5-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)-5-propylpyrimidine | 1346529-68-7 | C25H31FN4O |
| —— | 7-ethoxy-2,3-dihydro-2,2-dimethyl-5-(2-methyl-2-propenyl)benzofuran | 363185-95-9 | C16H22O2 |
| —— | 1280224-96-5 | C18H20O4 | |
| —— | tert-butyl 2,3-dibromo-6-chloro-2,3-dihydrobenzofuran-7-carbamate | 412349-17-8 | C13H14Br2ClNO3 |
| —— | N-[5-[2-[2-[5-(2,3-dihydro-1-benzofuran-3-carbonylamino)-1,3,4-thiadiazol-2-yl]ethylsulfanyl]ethyl]-1,3,4-thiadiazol-2-yl]-2,3-dihydro-1-benzofuran-3-carboxamide | 1439390-79-0 | C26H24N6O4S3 |
| —— | 2-(bis(2,3-dihydroxybenzofuran-5-yl)methyl)-1,1-dimethylhydrazinium chloride | 1372721-70-4 | C19H22N2O2*ClH |
| —— | 5-bromo-2,3-dihydro-2,2-dimethyl-7-(3-bromo-propoxy)-benzofuran | 1089210-35-4 | C13H16Br2O2 |
| —— | (2,3-Dihydro-benzofuran-5-yl)-p-tolyl-methanol | 87901-68-6 | C16H16O2 |
| —— | 2-[1-(5-isopropyl-[1,2,4]oxadiazol-3-yl)-piperidin-4-yl]-5-(4-methanesulfonylmethyl-phenyl)-2,3-dihydro-furo[2,3-c]pyridine | 1391081-36-9 | C25H30N4O4S |
| —— | Thioacetic acid S-[2-(2,3-dihydro-benzofuran-2-ylsulfanyl)-ethyl] ester | 34045-69-7 | C12H14O2S2 |
| —— | (S)-8-ethyl-6-trifluoromethoxy-2-trifluoromethyl-2H-chromene-3-carboxylic acid (S)-(-)-N-benzyl-α-methylbenzylamine salt | 874359-58-7 | C14H10F6O4*C15H17N |
| —— | 5-Iodo-3-iodomethyl-2,2,6-trimethyl-2,3-dihydro-benzofuran-4-ol | 79158-46-6 | C12H14I2O2 |
| —— | (5aS,7S,9R,9aR)-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-9-hydroxy-4-methoxy-9a(5aH)-dibenzofurnacetic acid ethyl ester | 1268868-65-0 | C23H36O6Si |
| —— | 3,4-dihydro-7-methoxy-8-methyl-spiro<2H-1-benzopyran-2,1'-cycloheptane>-4-ol | 135300-01-5 | C17H24O3 |
| —— | 2-[(2,3-dihydro-1-benzofuran-5-ylmethyl)sulfanyl]-5-(tetrahydro-2H-pyran-2-yloxy)pyrimidin-4(3H)-one | 1417817-90-3 | C18H20N2O4S |
| —— | 3,5,5a,10b-Tetrahydro-3,9,10b-trimethyl-benzofuro<2,3-d>azepin-4-on | 86658-38-0 | C15H17NO2 |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-(3,4-dimethylphenyl)amine | 852115-04-9 | C17H20N2O |
| —— | allyl 2,3-dihydro-5-hydroxy-2-methylbenzofuran-4-carboxylate | 84213-15-0 | C13H14O4 |
| —— | (+/-)-{[7-(2-methoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-75-5 | C18H21NO2 |
| —— | (5aR,6S,7S,9R,9aR)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester | 1268868-64-9 | C30H41BrO6Si |
| —— | N-(2,3-Dihydro-benzofuran-2-ylmethyl)-N',N'-dimethyl-N-pyridin-2-yl-ethane-1,2-diamine | 47234-44-6 | C18H23N3O |
| —— | 2-(1-acetoxy-1-methylethyl)-2,3-dihydrobenzofuran | 72446-44-7 | C13H16O3 |
| —— | (3aS,6aS,11bR)-8-methoxy-5-oxo-1,2,3,3a,4,5,6,6a-octahydrobenzofuro[3,2-d]indole-11-carbaldehyde | 1393565-20-2 | C16H17NO4 |
| —— | 2-(2,3-dihydro-benzofuran-5-ylmethyl)-2H-pyrazol-3-ylamine | 1157614-58-8 | C12H13N3O |
| —— | 6,7-Dichloro-5-((E)-3-cyclohexylamino-3-methylsulfanyl-acryloyl)-2,3-dihydro-benzofuran-2-carboxylic acid | 126200-66-6 | C19H21Cl2NO4S |
| —— | 3,6,7,8-tetrahydro-2H-furo[2,3-g]chromene | 1043541-90-7 | C11H12O2 |
| —— | ethyl 2-((2S,3R,4S)-4-((2-hydroxy-3-methylphenyl)amino)-3-methyl-3-nitrochroman-2-yl)acetate | 1266339-63-2 | C21H24N2O6 |
| —— | [(1S)-1-[(2S,3S)-3-[(4-bromophenyl)methylamino]-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-yl]but-3-enyl] acetate | 1016896-66-4 | C25H30BrNO6 |
| —— | 4b-Methyl-10a-phenyl-4b,10a-dihydro-5,10-dioxa-benzo[b]biphenylene | 37891-43-3 | C21H16O2 |