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 |
|---|---|---|---|
| —— | (+/-)-2-(1-Hydroxy-2-carbamoyloxy-ethyl)-2,3-dihydro-benzofuran | 3655-36-5 | C11H13NO4 |
| —— | 3-(4,6-dimethoxy-3-methyl-2,3-dihydro-benzofuran-2-yl)-propionic acid methyl ester | 101499-70-1 | C15H20O5 |
| —— | trans-4-acetoxy-3,4-dihydro-3,8-dihydroxy-2H-1-benzopyran | 106662-68-4 | C11H12O5 |
| —— | 7-(chloromethyl)-5-cyclopentyl-2,2-dimethyl-2,3-dihydrobenzofuran | 1352740-53-4 | C16H21ClO |
| —— | 7-(chloromethyl)-5-fluoro-2-(methoxymethyl)-2-methyl-2,3-dihydrobenzofuran | 1352740-41-0 | C12H14ClFO2 |
| —— | 3-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-2,3,5-trimethylphenyl)propanoic acid | 1234844-72-4 | C23H27ClO4 |
| —— | [(S)-3-(4-amino-5-fluoro-pyrimidin-2-yloxy)-pyrrolidin-1-yl]-[2-(2,3-dihydro-benzofuran-5-yl)-thiazol-4-yl]-methanone | 1033839-16-5 | C20H18FN5O3S |
| —— | 2,2-diethyl-5-fluoro-2,3-dihydrobenzofuran | 1352740-22-7 | C12H15FO |
| —— | N-Hydroxy-2-{4-[4-(2,3-dihydrobenzofuran-5-yl)-3-methylphenyl]-1,2,3,6-tetrahydropyridin-1-ylsulphonyl}acetamide | 227304-45-2 | C22H24N2O5S |
| —— | (S)-9-[3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-2-methyl-2,3,4,5-tetrahydropyrido[2,3-f][1,4]oxazepine | 1383377-74-9 | C19H19FN4O |
| —— | (+/-)-2,3-dihydro-3β,5-dimethylbenzofuran-2β-ol | 76650-22-1 | C10H12O2 |
| —— | (9aS)-8-acetyl-N-(3,5-dimethylbenzyl)-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925439-70-9 | C26H25NO7 |
| —— | 6-chloro-4-(chloromethyl)-2,2-dimethyl-2,3-dihydrobenzofuran | 1234845-42-1 | C11H12Cl2O |
| —— | N-(5-chloro-7-methyl-2,3-dihydro-1-benzofuran-3-yl)-6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxamide | 1294002-68-8 | C20H19ClN4O3 |
| —— | 1'(E),3'(E)-2,3-dihydro-5,7-dimethoxy-2-<1-(1,3-pentadienyl)>benzofuran | 129257-92-7 | C15H18O3 |
| —— | 6-t-butyl-5-hydroxy-2,2-dimethyl-4-isopropyl-2,3-dihydrobenzofuran | 216313-90-5 | C17H26O2 |
| —— | 1-(2,3-Dihydro-1-benzofuran-6-yl)-2,2,2-trifluoroethan-1-one | 1934405-12-5 | C10H7F3O2 |
| —— | 11-bromo-6,12-dimethyl-11,12-dihydro-6H-6,12-epoxydibenzo[b,f]oxocine | 627105-73-1 | C17H15BrO2 |
| —— | (2,3-Dihydro-benzofuran-3-yl)-(3-nitro-phenyl)-amine | 126884-72-8 | C14H12N2O3 |
| —— | 3-Isopropyl-6,9-dimethyl-7-nitro-2,3-dihydro-benzo[de]chromen-3-ol | 764713-60-2 | C17H19NO4 |
| —— | 6,7-Dichloro-5-((E)-3-methylsulfanyl-3-phenylamino-acryloyl)-2,3-dihydro-benzofuran-2-carboxylic acid | 126200-47-3 | C19H15Cl2NO4S |
| —— | (S)-2-ethenyl-2,6-dimethyl-2,3-dihydrobenzofuran | 1071984-91-2 | C12H14O |
| —— | 6-bromo-N-(propan-2-yl)-2,3-dihydro-1-benzofuran-3-amine | 1504288-64-5 | C11H14BrNO |
| —— | N'-tert-butyl-N-2,4-dimethyl-2,3-dihydrobenzofuran-5-carbohydrazide | 1033621-23-6 | C15H22N2O2 |
| —— | methyl 3-[(2R)-2-(4-Phenylbutyl)-2,3-dihydrobenzo[b]furan-4-yl]propanoate | 532399-70-5 | C22H26O3 |
| —— | 2-Aminomethyl-6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran | 77514-42-2 | C14H11Cl2NO2S |
| —— | (R,S)-5-(methanesulfonylamino-methyl)-2,3-dihydro-benzofuran-2-carboxylic acid | 847949-10-4 | C11H13NO5S |
| —— | 6,9-Dimethyl-7-nitro-3-trifluoromethyl-2,3-dihydro-benzo[de]chromen-3-ol | 764714-04-7 | C15H12F3NO4 |
| —— | (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-N-(2-fluorobenzyl)-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925439-35-6 | C24H20FNO7 |
| —— | 2-((4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)thio)-acetic acid | 1234842-23-9 | C19H19ClO4S |
| —— | (5-fluoro-7-(hydroxymethyl)-2,3-dihydrobenzofuran-2-yl)methyl acetate | 1352740-44-3 | C12H13FO4 |
| —— | (+/-)-2-(azidomethyl)-5-methyl-7-phenyl-2,3-dihydro-1-benzofuran | 852116-40-6 | C16H15N3O |
| —— | 2-(3-fluoro-4-((5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)cyclopropanecarboxylic acid | 1234843-74-3 | C21H20F2O4 |
| —— | 1-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)pyrrolidin-2-one | 1325189-72-7 | C12H12BrNO2 |
| —— | deuterio(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol | 1234847-87-0 | C11H13ClO2 |
| —— | 7-bromo-5-chloro-4-methoxy-3,3-dimethyl-2,3-dihydrobenzofuran | 1597548-48-5 | C11H12BrClO2 |
| —— | 7-Benzofuranpropanoic acid, 5-chloro-2,3-dihydro-I(2)-methyl- | 1781890-37-6 | C12H13ClO3 |
| —— | (+/-)-α,β-Bis-cyclohexylamino-2,2'-methylendioxy-diphenylethan | 108063-88-3 | C27H36N2O2 |
| —— | (3aS,5aS,10bR,10cR)-3,3-Dimethoxy-3,3a,4,5a,10b,10c-hexahydro-6-oxa-cyclopenta[c]fluoren-5-one | 73961-65-6 | C17H18O4 |
| —— | 114781-40-7 | C28H27O14Yb | |
| —— | 10b-Chlormethyl-2,5a,9-trimethyl-5a,10b-dihydro-benzofuro<2.3-b>benzofuran | 59521-01-6 | C18H17ClO2 |
| —— | 2,3-dihydro-3-ethyl-2-piperidinobenzofuran-5-yl methanesulphonate | 26225-65-0 | C16H23NO4S |
| —— | (R)-2-benzyl-2,3-dihydrobenzofuran | 1372790-96-9 | C15H14O |
| —— | 8-(2,4,6-trichlorophenyl)-6-(benzylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine | 488125-27-5 | C24H20Cl3NOS |
| —— | 8-(2,4,6-trichlorophenyl)-6-ethyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine | 488124-96-5 | C19H18Cl3NO |
| —— | (R)-ethyl 5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylate | 1403663-21-7 | C11H11ClO3 |
| —— | 1,2,3,5,5a,10b-Hexahydro-9,10b-dimethyl-benzofuro<2,3-d>azepin-4-on | 86658-28-8 | C14H17NO2 |
| —— | N-[(E)-[(1E)-1-(phenylhydrazinylidene)-2,3,8,9-tetrahydropyrano[3,2-f]chromen-10-ylidene]amino]aniline | 61678-11-3 | C24H22N4O2 |
| —— | methyl 6-((2,4-dichlorobenzyl)oxy)-3-(methoxymethyl)-2,3-dihydro-1-benzofuran-3-carboxylate | 1452478-31-7 | C19H18Cl2O5 |
| —— | methyl [(1R,2R,3aS,9aR)-2-t-butyldiphenylsilyloxy-1-[(3S,5S,1E)-3-hydroxy-5-methyl-1,8-nonadien-1-yl]-2,3,3a,9a-tetrahydro-1H-cyclopenta[b][1,4]benzodioxin-5-yl]oxyacetate | 120962-40-5 | C40H50O7Si |