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 |
|---|---|---|---|
| —— | 1-(4-methoxy-phenyl)-1<i>H</i>-naphtho[2,1-<i>b</i>]furan-2-one | 23860-99-3 | C19H14O3 |
| —— | (2R,1'R)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-hydroxybenzofuran | 470459-94-0 | C14H18O4 |
| —— | 6,7-Dichloro-5-{(E)-3-[(furan-2-ylmethyl)-amino]-3-methylsulfanyl-acryloyl}-2,3-dihydro-benzofuran-2-carboxylic acid tert-butyl ester | 126201-02-3 | C22H23Cl2NO5S |
| —— | 1334114-92-9 | C19H23ClN2O3S | |
| —— | (R)-1-[3-((R)-cyclohexyl-hydroxy-phenyl-methyl)-isoxazol-5-ylmethyl]-3-(2,3-dihydro-benzofuran-5-yloxy)-1-azonia-bicyclo[2.2.2]octane chloride | 1208426-54-3 | C32H39N2O4*Cl |
| —— | (+/-)-{[5-chloro-7-(2,3-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-61-9 | C16H14ClF2NO |
| —— | acetic acid (R)-(Z)-1-((2R,3R)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)-2-methylpent-2-ene-1,5-diol | 628299-87-6 | C25H41BrO4Si |
| —— | (1S,2S)-1-(4-fluorophenyl)-2-nitro-1,2-dihydronaphtho[2,1-b]furan | 1424936-88-8 | C18H12FNO3 |
| —— | 1334477-97-2 | C23H27BrO2 | |
| —— | methyl (R)-6,7-dichloro-5-(N,N-dimethylsulfamoyl)-2,3-dihydrobenzo<b>furan-2-carboxylate | 118196-06-8 | C12H13Cl2NO5S |
| —— | (2R)-N-{(2R)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-pyridinyl]-2-hydroxyethyl}-6-iodo-3,4-dihydro-2H-chromene-2-carboxamide | 474114-45-9 | C23H24IN3O3 |
| —— | 2-Isocyanato-2,3-dihydro-1-benzofuran | 1016738-92-3 | C9H7NO2 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(3,4,5-trimethyl-1H-pyrazol-1-yl)-acetamide | 1048959-49-4 | C25H36N4O2 |
| —— | 7-piperidin-1-yl-6,7-dihydro-5H-[1,4]oxazino[2,3,4-ij]quinolin-3-one | 23866-23-1 | C16H20N2O2 |
| —— | 2-(2'-Methyl-propenyl)-4,5,6,7-tetrachlor-1,3-benzo-dioxid | 30310-17-9 | C11H8Cl4O2 |
| —— | Acetic acid 2,3,7-triacetoxy-chroman-5-yl ester | 36048-16-5 | C17H18O9 |
| —— | 2-((4aS,9bR)-6-methoxy-1,2,4,4a-tetrahydro-9bH-spiro[dibenzo[b,d]furan-3,2'-[1,3]dioxolane]-9b-yl)ethan-1-amine | 1334529-19-9 | C17H23NO4 |
| —— | 7-(furan-3-yl)-2,2-dimethyl-2,3-dihydrobenzofuran | 1448245-77-9 | C14H14O2 |
| —— | (2S,3R,4R)-2-ethoxy-3,4-dimethyl-3,4-dihydro-2H-chromene | 102102-98-7 | C13H18O2 |
| —— | 17-(cyclopropylmethyl)-3-methoxy-10-methylene-6-oxamorphinan | 130788-09-9 | C21H27NO2 |
| —— | 2,3-dihydro-2,2-dimethyl-7-(3-chloro-propoxy)-benzofuran-5-ylsulfonic acid amide | 1089210-24-1 | C13H18ClNO4S |
| —— | 8-methoxy-2'-methoxyneoflavene | 1159707-97-7 | C17H16O3 |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid {3-[5-(3-chloro-phenyl)-2-methyl-thiazole-4-carbonyl]-thiazolidin-2-ylmethyl}-amide | 1204583-98-1 | C24H22ClN3O3S2 |
| —— | (1S)-1-[(2R)-2,3-dihydro-benzofuran-2-yl]-2-methyl-propane-1,2-diol | 1030350-09-4 | C12H16O3 |
| —— | 4-(1-(4-bromophenyl)vinyl)-5-methyl-2,3-dihydrobenzofuran | 1582778-59-3 | C17H15BrO |
| —— | 2,3-dihydro-2,2-dimethyl-5-bromo-7-(oxiranyl-methoxy)-benzofuran | 250289-98-6 | C13H15BrO3 |
| —— | (1R,3R)-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 | 1443020-80-1 | C31H38N2O7 |
| —— | 6,7-dichloro-5-(3-furfurilamino-3-methylthio-2-propenoyl)-2,3-dihydro-2-benzo<b>furancarboxylic acid | 126200-67-7 | C18H15Cl2NO5S |
| —— | (R)-1-[3-((R)-cyclohexyl-hydroxy-phenyl-methyl)-[1,2,4]oxadiazol-5-ylmethyl]-3-(2,3-dihydro-benzofuran-5-yloxy)-1-azonia-bicyclo[2.2.2]octane chloride | 1208426-51-0 | C31H38N3O4*Cl |
| —— | (5'aS,9'aS)-4'-methoxyspiro[1,3-dioxolane-2,7'-5a,6,8,9-tetrahydrodibenzofuran]-9'a-carbonitrile | 1334171-15-1 | C16H17NO4 |
| —— | 1334114-36-1 | C19H24N2O3S | |
| —— | (+/-)-1-(5-chloro-2-methyl-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine | 852125-88-3 | C16H16ClNO |
| —— | 2-pentyl-5-hydroxy-7-methyl-4-(2'-hydroxypropylimino)-4H-2,3-dihydrobenzopyran | 88879-93-0 | C18H27NO3 |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid [3-(5-m-tolyl-thiazole-4-carbonyl)-thiazolidin-2-ylmethyl]-amide | 1204585-51-2 | C24H23N3O3S2 |
| —— | 3,3-dimethyl-7-t-butyl-5-[(1S,2S)-3-hydroxyl-1,2-methano-1-methyl-propyl]-2,3-dihydro-benzofuran | 623176-01-2 | C19H28O2 |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid {3-[5-(3-methoxy-phenyl)-thiazole-4-carbonyl]-thiazolidin-2-ylmethyl}-amide | 1204585-50-1 | C24H23N3O4S2 |
| —— | ethyl 2,3-dihydro-6,7-dimethoxybenzofuran-2-carboxylate | 90246-77-8 | C13H16O5 |
| —— | 2-Cyclopropylmethyl-5-methyl-1,2,3,4,9,9a-hexahydro-10-oxa-2-aza-anthracen-4a-ol | 26405-89-0 | C17H23NO2 |
| —— | 4-(1-(4-chlorophenyl)vinyl)-5-methyl-2,3-dihydrobenzofuran | 1582778-57-1 | C17H15ClO |
| —— | 4-iodo-2,3-dihydrobenzofuran-3-amine | 1337380-18-3 | C8H8INO |
| —— | dimethylcarbamic acid 3-(2-methanesulfonylaminopyridin-4-ylmethyl)-4-methyl-2H-1-benzopyran-7-yl ester | 1104543-66-9 | C20H23N3O5S |
| —— | acetic acid (R)-(E)-1-((2R,3R)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)-2-methylpent-2-ene-1,5-diol | 628299-80-9 | C25H41BrO4Si |
| —— | 2-Hydroxymethyl-6-methoxycoumaran | 99186-37-5 | C10H12O3 |
| —— | 3-Phenyl-1-(2,2,4-triethyl-chroman-3-yl)-pentan-1-one | 76011-77-3 | C26H34O2 |
| —— | 2-ethenyl-3,4-dihydro-6-methyl-2H-1-benzopyran | 91713-36-9 | C12H14O |
| —— | 7-Bromo-2-(iodomethyl)-5-methyl-2,3-dihydro-1-benzofuran | 2375273-90-6 | C10H10BrIO |
| —— | 4-amino-2-(ethylsulfanylmethyl)phenolate;copper(1+) | 84934-66-7 | C9H12CuNOS |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid {3-[2-dimethylamino-5-(3-methoxy-phenyl)-thiazole-4-carbonyl]-thiazolidin-2-ylmethyl}-amide | 1204585-49-8 | C26H28N4O4S2 |
| —— | 4-(2-benzyl-2,3-dihydrobenzofuran-5-yl)phenol | 1394958-24-7 | C21H18O2 |
| —— | (Z)-9-N-(tert-butoxycarbonyl)-N-methylaminomethyl-6-methoxy-9b-(2-methoxyvinyl)-3,4,4a,9b-tetrahydrodibenzofuran | 312920-65-3 | C23H31NO5 |