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 |
|---|---|---|---|
| —— | 7,8-Dichloro-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxine-5-sulfonic acid ethyl-methyl-amide | 120588-72-9 | C12H15Cl2NO5S |
| —— | N-methyl-2,3-dihydro-2,2-dimethyl-7-(3-chloro-propoxy)-benzofurane-5-sulfonamide | 1089210-26-3 | C14H20ClNO4S |
| —— | Ethyl 3-(2-ethoxy-2-oxoethyl)-2-[(4-methoxyphenyl)methyl]-1,2-benzoxazole-3-carboxylate | 1417406-98-4 | C22H25NO6 |
| —— | 2-hydroxyl-2-trifluoromethyl-3-ethoxycarbonyl-7-(N,N-diethylamino)-2H-1-chromene | 1332635-71-8 | C17H20F3NO4 |
| —— | 7-ethyl-3,3-dimethyl-5-(2-pyridyl N-oxide)-2,3,4,5-tetrahydro-1-benzoxepin-5-ol | 157986-58-8 | C19H23NO3 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(1H-tetrazol-1-yl)-acetamide | 1048959-22-3 | C20H28N6O2 |
| —— | 5-Brom-2,3-dihydro-benzofuran-3-ol | 5590-43-2 | C8H7BrO2 |
| —— | 6-allyl-5-(benzyloxy)-2,3-dihydro-3,3-dimethyl-2-<2-hydroxy-2-<4-(methylthio)phenyl>ethyl>benzofuran | 139201-39-1 | C29H32O3S |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-(3-chloro-4-fluorophenyl)amine | 852115-32-3 | C15H14ClFN2O |
| —— | 2-Cyclohexyl-2,3-dihydro-1-benzofuran-5-carbaldehyde | 109209-61-2 | C15H18O2 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)thieno[2,3-b]pyridine-2-carboxamide | 1048960-03-7 | C25H29N3O2S |
| —— | 1-[3-(2,2-dimethyl-2,3-dihydro-benzofuran-3-yl)-3H-imidazol-4-yl]-ethanol | 1034919-30-6 | C15H18N2O2 |
| —— | 2-(Di-n-butylaminomethyl)-2,3-dihydrobenzofuran | 21130-04-1 | C17H27NO |
| —— | (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-N-(2,3,5-trimethyl-6-propylbenzyl)-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925440-23-9 | C30H33NO7 |
| —— | 7-Bromo-5-methyl-2,3-dihydro-1-benzofuran-3-ol | 1491101-20-2 | C9H9BrO2 |
| —— | 5,7-dichloro-2,3-dihydrobenzofuran-3-ol | 5688-57-3 | C8H6Cl2O2 |
| —— | 7,8-Dichloro-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxine-5-sulfonic acid benzyl-methyl-amide | 120588-70-7 | C17H17Cl2NO5S |
| —— | methyl 3-acetylimino-2-(2,3,4,5,6,7-hexahydro-1H-azepinyl)-2,3-dihydrobenzofuran-2-carboxylate | 105443-76-3 | C18H22N2O4 |
| —— | 4,5,6,7-tetrabromo-2-(1,4-dimethyl-penta-1,3-dienyl)-benzo[1,3]dioxole | 24863-63-6 | C14H12Br4O2 |
| —— | 3-(4,7-dimethoxy-2,3-dihydro-benzofuran-6-yloxy)-crotonic acid | 100884-62-6 | C14H16O6 |
| —— | (2R)-2-[4-[(4-chlorophenyl)methyl]-5-methyl-1,2,4-triazol-3-yl]-N-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)pyrrolidine-1-carboxamide | 1140491-52-6 | C24H26ClN5O2 |
| —— | 1269598-92-6 | C13H18O2 | |
| —— | Acetic acid 6,7-dichloro-5-methylsulfamoyl-2,3-dihydro-benzofuran-2-ylmethyl ester | 103969-33-1 | C12H13Cl2NO5S |
| —— | N-[4-(2,3-dihydro-1-benzofuran-5-yl)-4-methyl-5,6-dihydro-1,3-thiazin-2-yl]methanesulfonamide | 935988-14-0 | C14H18N2O3S2 |
| —— | 7-Chlor-2-(3-methoxy-propylaminomethyl)-2,3-dihydro-benzofuran | 17793-77-0 | C13H18ClNO2 |
| —— | 1-[(2R,3S)-3-(2-ethoxyphenoxy)-2,3-dihydro-1-benzofuran-2-yl]-N-methylmethanamine hydrochloride | 1033009-65-2 | C18H21NO3*ClH |
| —— | Methyl 3-[2-((3E)-4-Phenylbut-3-enyl)(2R)-2,3-dihydrobenzo[b]furan-4-yl]propanoate | 532399-69-2 | C22H24O3 |
| —— | (2S,4R,5R)-methyl 4-(3-bromophenyl)-5-(4-bromophenylamino)-2-(2-methoxy-2-oxoethyl)-4,5-dihydrobenzo[d][1,3]dioxepine-4-carboxylate | 1559074-29-1 | C26H23Br2NO6 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(5-methyl-1H-pyrazol-1-yl)-acetamide | 1048959-77-8 | C23H32N4O2 |
| —— | N'-tert-butyl-N-2,3-dihydro-2-methylbenzofuran-4-carbohydrazide | 1261963-76-1 | C14H20N2O2 |
| —— | 4B,9b-dimethyl-4b,9b-dihydro-benzofuro[3,2-b]benzofuran-3,8-diol | 860692-20-2 | C16H14O4 |
| —— | 5-methyl-2,3-dihydro-benzofuran-3-ylamine; hydrochloride | 669-44-3 | C9H11NO*ClH |
| —— | 6-fluoro-5-nitro-2,3-dihydrobenzofuran | 1632261-95-0 | C8H6FNO3 |
| —— | Trimethyl-(7-methyl-2,3-dihydro-benzofuran-2-ylmethyl)-ammonium; bromide | 16586-08-6 | Br*C13H20NO |
| —— | (2,3-dihydro-benzofuran-5-yl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-amine | 1201196-01-1 | C16H15F3N2O |
| —— | 5-[1-(4-fluorophenyl)ethylidene]-2,3-dihydro-1-benzofuran-1-ium | 86766-81-6 | C16H14FO |
| —— | 4-[3-(2,3-dihydro-benzofuran-2-ylmethoxy)benzylidene]-N-pyridazin-3-piperidine-1-carboxamide | 1191400-98-2 | C26H26N4O3 |
| —— | 3-bromo-3,4-dihydro-4-hydroxy-2,2,3-trimethyl-2H-1-benzopyran-6-carbonitrile | 135799-88-1 | C13H14BrNO2 |
| —— | 2,4,6-Tribenzyloxy-2-benzyl-cumaran-3-on | 13195-97-6 | C36H30O5 |
| —— | 3,4,17β-Trihydroxy-17α-methyl-9,10-seco-B-norandrosta-1,3,5-trien-9-on-4,9-hemiketal-3-methansulfonat | 7635-72-5 | C20H28O6S |
| —— | dimethyl 2-((4R)-3,4-dihydro-2-hydroxy-8-methoxy-2H-chromen-4-yl)malonate | 1346013-14-6 | C15H18O7 |
| —— | 5-[1-(4-methoxyphenyl)ethylidene]-2,3-dihydro-1-benzofuran-1-ium | 86766-79-2 | C17H17O2 |
| —— | 1-methyl-4-((5-nitro-1,3-benzodioxol-2-yl)methyl)piperazine | 873557-35-8 | C13H17N3O4 |
| —— | 2,4-Dimethyl-2,3-dihydro-1-benzofuran-5-carbonyl chloride | 1126854-67-8 | C11H11ClO2 |
| —— | 4-hydroxy-2-isopropenyl-2,3-dihydrobenzofuran-5-carbaldehyde | 581096-50-6 | C12H12O3 |
| —— | 6,7-Dichloro-5-(2-morpholin-4-yl-ethylsulfamoyl)-2,3-dihydro-benzofuran-2-carboxylic acid; hydrochloride | 103969-07-9 | C15H18Cl2N2O6S*ClH |
| —— | 14-[2-(4-(2,3-di-(tert-butyloxycarbonyl)-guanidino)-methyl-[1,2,3]triazol-1-yl)-ethyl]-6,7,9,10,13,14,15,16,18,19,21,22-dodecahydro-12H-5,8,11,17,20,23-hexaoxa-14-aza-benzocyclohenicosene-2,3-dicarboxylic acid dimethyl ester | 1221569-85-2 | C38H59N7O14 |
| —— | [(2S,3R)-2-(5'-Allyl-6,2'-dimethoxy-biphenyl-3-yl)-7-(5-allyl-2-methoxy-phenyl)-5-methoxy-2,3-dihydro-benzofuran-3-yl]-methanol | 138591-35-2 | C37H38O6 |
| —— | 1-cyclohexylmethyl-5-[2-(2,3-dihydrobenzofuran-5-yl)thiazol-4-yl]-2-methyl-1H-pyrrole-3-carboxylic acid butylamide | 726179-69-7 | C28H35N3O2S |
| —— | Acetic acid 6,7-dichloro-5-nitro-2,3-dihydro-benzofuran-2-ylmethyl ester | 113730-02-2 | C11H9Cl2NO5 |