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 |
|---|---|---|---|
| —— | (4S)-3-[(E)-3-[[[(E)-3-[(4S)-5,5-bis(2-methoxy-5-methylphenyl)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]-3-oxoprop-1-enyl]-dimethylsilyl]oxy-dimethylsilyl]prop-2-enoyl]-5,5-bis(2-methoxy-5-methylphenyl)-4-propan-2-yl-1,3-oxazolidin-2-one | 1201848-25-0 | C54H68N2O11Si2 |
| —— | (+/-)-{[7-(2,5-difluorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-47-1 | C16H14F3NO |
| —— | (+/-)-4aα-<(Methylsulfonyl)oxy>-6-methoxy-9-chloro-9bβ-<2-(formylamino)ethyl>-1,2,3,4,4aβ,9b-hexahydrodibenzofuran | 90149-46-5 | C17H22ClNO6S |
| —— | 6-[(1,3,5,5-tetramethylhexyl)-oxy]-2,3-dihydrobenzofuran | 51079-78-8 | C18H28O2 |
| —— | Carbamic acid, [(3R)-1-(2,3-dihydro-4-benzofuranyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl ester | 319478-18-7 | C17H24N2O3 |
| —— | cis-1,2,2a,8a-tetrahydro-2a,5,8a-trimethyl-8-methylenebenzo<b>cyclobuta<e>pyran | 138629-66-0 | C15H18O |
| —— | Acetic acid 2,2-dibenzyl-4,6-di-tert-butyl-2,3-dihydro-benzofuran-5-yl ester | 1027047-00-2 | C32H38O3 |
| —— | 3-(7-Formyl-3-methoxy-1-oxo-6,7,8,9-tetrahydro-2-oxa-7-aza-benzo[cd]azulen-9a-yl)-propionic acid methyl ester | 108937-03-7 | C17H19NO6 |
| —— | Acetic acid (4aS,9bR)-(1,2,4a,9b-tetrahydro-dibenzofuran-4-yl) ester | 125812-21-7 | C14H14O3 |
| —— | 937254-93-8 | C17H16FN3O4 | |
| —— | 5-bromo-3-(4-ethoxyphenyl)-2,3-dihydrobenzofuran | 1190074-02-2 | C16H15BrO2 |
| —— | 2-(chlorocarbonyl)-2-(2,3-dihydrobenzofuran-7-yl)hydrazinecarboxylic acid, methyl ester | 80959-16-6 | C11H11ClN2O4 |
| —— | 2-methyl-5,7-dichloro-2-(2,4-dichlorophenoxy)methylcoumaran | 119561-15-8 | C16H12Cl4O2 |
| —— | (S)-2,3-dihydrobenzofuran-3-amine hydrochloride | 1459793-02-2 | C8H9NO*ClH |
| —— | 1196967-58-4 | C25H35N3O4S | |
| —— | trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[3-(2,5-dioxo-pyrrolidin-1-yl)-propyl]-3-methoxy-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid | 1443020-17-4 | C33H42N2O6 |
| —— | triisopropyl(3-(2-methyl-2,3-dihydrobenzofuran-2-yl)prop-1-yn-1-yl-1-13C)silane | 1203447-58-8 | C21H32OSi |
| —— | N-[2-((5aR,6S,9aS)-1-Formyl-6-hydroxy-4-methoxy-9-oxo-6,7,8,9-tetrahydro-5aH-dibenzofuran-9a-yl)-ethyl]-N-methyl-formamide | 232613-19-3 | C18H21NO6 |
| —— | N'-tert-butyl-N-2,2,4-trimethyl-2,3-dihydrobenzofuran-5-carbohydrazide | 1126854-76-9 | C16H24N2O2 |
| —— | (+/-)-{[7-(3-chloro-4-fluorophenyl)-5r-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852120-05-9 | C17H17ClFNO2 |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-phenylamine | 852114-88-6 | C15H16N2O |
| —— | 84824-29-3 | C40H51O2Ta | |
| —— | (3aR,5aR,10bS,10cS)-5-Eth-(Z)-ylidene-1,2,3a,4,5,5a,10b,10c-octahydro-6-oxa-cyclopenta[c]fluoren-3-one | 73961-69-0 | C17H18O2 |
| —— | 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl ethylaminosulfonate | 55531-05-0 | C13H19NO5S |
| —— | 2-[4-[5-(1-benzylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-2-methyl-3H-1-benzofuran-2-yl]piperidin-1-yl]-5-propylpyrimidine | 1346529-34-7 | C33H40N4O3S |
| —— | methyl (2R,4aR,9aR)-5-bromo-2-(methoxymethoxy)-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-7-carboxylate | 1353178-23-0 | C20H27BrO5 |
| —— | methyl 4-[(1R,2R,3aS,8bS)-2-hydroxy-1-[(E,3R,4S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoate | 223556-67-0 | C25H32O5 |
| —— | 2,2,3,3-tetramethyl-2,3-dihydro-1-benzofuran-7-carbaldehyde | 929301-69-9 | C13H16O2 |
| —— | 5a,10a-dihydro-5a,10b-butanodibenzo<2,3:4,5>furo<2,3-b>-furan | 127245-05-0 | C18H16O2 |
| —— | 8-(2,4-dichlorophenyl)-N-methyl-N-cyclohexyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488124-82-9 | C24H28Cl2N2O |
| —— | 6-Bromo-4-methylsulfonyl-2,3-dihydro-1-benzofuran | 1335496-48-4 | C9H9BrO3S |
| —— | 1391082-40-8 | C30H34N4O3 | |
| —— | 7-isopropyl-10-methyl-4a,10b-dihydro-1<i>H</i>-pyrano[3,4-<i>c</i>]chromene-2,4,5-trione | 130906-57-9 | C16H16O5 |
| —— | 2H-1-Benzopyran-6-carboxylic acid, 3,4-dihydro-3-(1H-imidazol-1-yl)-2-methyl-, cis-monohydrochloride | 89781-78-2 | C14H15ClN2O3 |
| —— | methyl 3-(dimethylamino)-2-(3-hydroxypentan-3-yl)-4-methoxy-2,3-dihydrobenzofuran-2-carboxylate | 1621007-63-3 | C18H27NO5 |
| —— | methyl (2R,4aR,9aR)-5-bromo-2-hydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-7-carboxylate | 1353178-21-8 | C18H23BrO4 |
| —— | ethyl 4-hydroxy-4H-chromene-3-carboxylate | 1642135-68-9 | C12H12O4 |
| —— | 1294518-48-1 | C21H18N2O5S2 | |
| —— | 11-<(tert-butyldimethylsilyl)oxy>-1,2,3,3a,3b,4,9b,10-octahydrobenz<b>indeno<5,4-d>pyran-4-one | 130043-10-6 | C22H30O3Si |
| —— | (+/-)-[(5-chloro-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-58-4 | C17H18ClNO2 |
| —— | 6-[2-(2-amino-1H-imidazol-5-yl)ethylamino]-1,3-bis(2,3-dihydro-1-benzofuran-5-ylmethyl)-1,3,5-triazine-2,4-dione | 1148128-11-3 | C26H27N7O4 |
| —— | 2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl dimethylaminosulfonate | 57161-67-8 | C14H19NO7S |
| —— | 3,3-Dimethyl-2,3-dihydro-1-benzofuran-6-amine | 1135492-28-2 | C10H13NO |
| —— | 3-hydroxy-3-phenylbenzofuran-2(3H)-one | 55190-56-2 | C14H10O3 |
| —— | 2-Methyl-2,3-dihydro-1-benzofuran-7-sulfonyl chloride | 1781955-21-2 | C9H9ClO3S |
| —— | (1S,2S)-7-bromo-2-nitro-1-phenyl-1,2-dihydronaphtho[2,1-b]furan | 1424936-92-4 | C18H12BrNO3 |
| —— | 1-(Diaminomethylidene)-2-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)guanidine | 6739-73-7 | C11H15N5O |
| —— | 3-(2-hydroxy-1,1-dimethylethylimino)-6-methoxy-1,3-dihydro-2-benzofuran-1-spirocyclohexane | 86917-36-4 | C18H25NO3 |
| —— | 1-[(3R)-3-(4-fluorophenyl)-2,3-dihydro-2-oxo-3-benzofuranyl]-1,2-hydrazinedicarboxylic acid,1,2-bis(phenylmethyl) ester | 1314114-32-3 | C30H23FN2O6 |
| —— | 7-[2-(2,2-dimethyl-4-trifluoromethyl-[1,3]dioxolan-4-yl)-1,1-dimethylethyl]-5-methylsulfanyl-2,3-dihydrobenzofuran | 727376-27-4 | C19H25F3O3S |