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 |
|---|---|---|---|
| —— | 2,4-Bis-(1-phenyl-ethyl)-4H-benzo[1,3]dioxine | 76369-14-7 | C24H24O2 |
| —— | Ethyl 4-cyano-2,3-dihydro-1-benzofuran-6-carboxylate | 1342299-73-3 | C12H11NO3 |
| —— | 7-methyl-2-oxo-3-phenyl-2,3-dihydro-benzofuran-4-carboxylic acid | 857543-59-0 | C16H12O4 |
| —— | (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine phosphate | 241136-32-3 | C20H32N2O3S*H3O4P |
| —— | (Z)-2-(3-(tert-butyldimethylsilyloxy)propylidene)-2,3-dihydrobenzofuran-3-ol | 1599371-54-6 | C17H26O3Si |
| —— | Ethyl dl-7-{N-(2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-7-yl)amino}heptanoate | 121454-24-8 | C21H31NO3 |
| —— | (R)-2-bromomethyl-7-(2',6'-dichloro-phenyl)-5-fluoro-2,3-dihydro-benzofuran | 852112-92-6 | C15H10BrCl2FO |
| —— | trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-propyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methyl-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid | 1443020-45-8 | C33H42N2O6 |
| —— | (+/-)-2-(azidomethyl)-7-(2-methylphenyl)-6-chloro-2,3-dihydro-1-benzofuran | 852118-12-8 | C16H14ClN3O |
| —— | N-[(3-pyrrolidin-1-yl-2H-1,4-benzoxazin-7-yl)carbamothioyl]furan-2-carboxamide | 85840-12-6 | C18H18N4O3S |
| —— | (2,2-dimethyl-3H-1-benzofuran-7-yl) N-carbonisocyanatidoyl-N-methylcarbamate | 84942-50-7 | C14H14N2O5 |
| —— | cis-3a,8b-dihydro-3,3a,6,8b-tetramethyl-1H-cyclopenta<b>benzofuran | 63023-41-6 | C15H18O |
| —— | 2,3-dihydro-3,3-dimethyl-2-ethylcarbonyloxybenzofuran-5-yl dimethylaminosulfonate | 57253-96-0 | C15H21NO6S |
| —— | (R)-3-methyl-2,3-dihydrobenzofuran-4-carboxaldehyde | 1051915-29-7 | C10H10O2 |
| —— | 6,8-dichloro-3,3-bis(diethylaminomethyl)-2,4-dihydrochromen-4-ol | 87669-62-3 | C19H30Cl2N2O2 |
| —— | 2H-1-Benzopyran-4-amine,N-(1,1-dimethylethoxy)-3,4-dihydro-3-methylene- | 137265-90-8 | C14H19NO2 |
| —— | 130251-10-4 | C40H40O12 | |
| —— | (+/-)-{[7-fluoro-5-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852125-21-4 | C16H15ClFNO |
| —— | 11-<(tert-butyldimethylsilyl)oxy>-1,2,3,3a,3b,4,9b,10-octahydrobenz<b>indeno<5,4-d>pyran-4-one | 134678-37-8 | C22H30O3Si |
| —— | 5-bromo-2-(1,2-dibromoethyl)-2,3-dihydrobenzo[b]furan | 936734-80-4 | C10H9Br3O |
| —— | (2E, 4E)-5-(3,3-dimethyl-7-fluoro-8-chloro-2,3-dihydrobenzoxepin-5-yl)-3-methylpenta-2,4-dienoic acid | 280585-51-5 | C18H18ClFO3 |
| —— | trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-propyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid | 1443019-69-9 | C33H42N2O7 |
| —— | [3-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl] acetate | 1026923-28-3 | C22H32N2O5 |
| —— | (2'S)-6'-bromo-2'-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7'-fluorospiro[1,3-dithiolane-2,4'-2,3-dihydrochromene] | 905455-04-1 | C16H18BrFO3S2 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-pyridin-4-ylacetamide | 1048960-27-5 | C24H31N3O2 |
| —— | 918311-52-1 | C25H27Cl3N2O5 | |
| —— | (+/-)-{[5-chloro-7-(2,5-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-68-6 | C16H14ClF2NO |
| —— | 2-[2-tert-Butyl-5-(2,3-dihydrobenzofuran-5-yl)-3H-imidazol-4-yl]-6-methylpyridine | 356559-85-8 | C21H23N3O |
| —— | (R)-methyl 3-(4-bromophenyl)-5-((S)-((S)-2-oxo-3-p-tolyl-2,3-dihydrobenzofuran-3-yl)(phenyl)methyl)-4,5-dihydroisoxazole-5-carboxylate | 1417999-32-6 | C33H26BrNO5 |
| —— | 5,7-dichloro-5-methoxyfuro<2,3b>-2,3-dihydrobenzofuran | 98192-40-6 | C11H10Cl2O3 |
| —— | [7-Methoxy-benzofuran-(3E)-ylidene]-acetonitrile | 39581-46-9 | C11H9NO2 |
| —— | N-(2,3-Dihydro-7-methyl-benzofuran-2-yl-methyl)-dimethylamin | 17349-67-6 | C12H17NO |
| —— | 5-bromo-4,6,7-trimethyl-2-(1-methyl-hexyl)-2,3-dihydro-benzofuran | 858791-42-1 | C18H27BrO |
| —— | (+/-)-{[7-fluoro-5-(4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-70-7 | C15H13F2NO |
| —— | (+/-)-{[5-cyclopentyl-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-63-5 | C21H25NO |
| —— | (2'R)-6'-bromo-2'-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7'-fluorospiro[1,3-dithiolane-2,4'-2,3-dihydrochromene] | 905454-96-8 | C16H18BrFO3S2 |
| —— | 1227077-78-2 | C23H20N2O7 | |
| —— | 7-methoxy-4-methyl-2-phenyl-4<i>H</i>-benz[<i>d</i>][1,3]oxazin-4-yl hydroperoxide | 412344-34-4 | C16H15NO4 |
| —— | tert-butyl (3S,4R)-(3-methyl-chroman-4-ylmethyl)carbamate | 1301745-85-6 | C16H23NO3 |
| —— | 4-anilino-7-nitro-3,5-dihydro-2<i>H</i>-furo[3,2-<i>c</i>]pyridin-6-one | 50839-26-4 | C13H11N3O4 |
| —— | methylsulfamic acid 3,3-dimethyl-2-morpholin-4-yl-2,3-dihydro-benzofuran-5-yl ester | 55562-05-5 | C15H22N2O5S |
| —— | 2-Chloro-1-(6-hydroxy-2,3-dihydro-benzofuran-5-yl)-ethanone | 57052-88-7 | C10H9ClO3 |
| —— | (1<i>RS</i>,2<i>RS</i>)-1-((3Ξ)-2,2,3-trimethyl-2,3-dihydro-benzofuran-5-yl)-propane-1,2-diol | 107821-44-3 | C14H20O3 |
| —— | (+/-)-2-(azidomethyl)-5-chloro-7-cyclohexyl-2,3-dihydro-1-benzofuran | 852113-11-2 | C15H18ClN3O |
| —— | 2-benzylidene-5-nitro-3H-1-benzofuran-3-ol | 1384475-78-8 | C15H11NO4 |
| —— | (+/-)-[6-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol | 852117-95-4 | C16H15FO2 |
| —— | (1a'S,7b'S)-methyl 1a',7b'-dihydrospiro[cyclohexane-1,2'-oxireno[2,3-c]chromene]-6'-carboxylate | 1215023-94-1 | C16H18O4 |
| —— | 3-(4-hydroxy-2,6-dimethyl-phenyl)-4,6-dimethyl-3<i>H</i>-benzofuran-2-one | 73499-76-0 | C18H18O3 |
| —— | (+/-)-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide | 1072073-69-8 | C15H19N3O |
| —— | 4β-hydroxy-6-methoxy-9bβ-N-methyl-N-allylcarboxamidomethylhexahydrodibenzofuran | 142641-97-2 | C19H25NO4 |