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 |
|---|---|---|---|
| —— | Deoxy-12.12α-dehydrorotenon-6a-<sup>14</sup>C | 5971-21-1 | C23H22O5 |
| —— | 5-(1-Chloro-2,2,2-trifluoro-1-phenyl-ethyl)-2,3-dihydro-benzofuran | 131543-78-7 | C16H12ClF3O |
| —— | Boc-Arg(Pbf)-Thz-OEt | 1458012-08-2 | C29H43N5O7S2 |
| —— | ethyl (3S,4R)-4-((R)-((((3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)oxy)sulfonyl)(phenyl)methyl)-2-oxochromane-3-carboxylate | 1202403-54-0 | C31H36O12S |
| —— | 1257099-20-9 | C25H23ClNO3PS | |
| —— | 4-amino-6,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl acetate | 113730-16-8 | C11H11Cl2NO3 |
| —— | 7-bromo-5-tert-butyl-2,3-dihydrobenzofuran | 1165739-48-9 | C12H15BrO |
| —— | 5-(6-Hydroxy-2,3-dihydro-1-benzofuran-3-yl)-1,3-thiazolidine-2,4-dione | 905724-84-7 | C11H9NO4S |
| —— | 5,6,6a,11a-tetrahydro-8-methoxybenzo[b]naphtho[2,1-d]furan | 1326704-91-9 | C17H16O2 |
| —— | 6-dodecylthiomethyl-5-hydroxy-2,4,7-trimethyl-2,3-dihydrobenzofuran | 1579996-42-1 | C24H40O2S |
| —— | 3,9-Dinitro-7-oxo-tetrahydrodibenzofuran | 66041-63-2 | C12H8N2O6 |
| —— | 2-(RS)-(2-hydroxyethyl)-2,3-dihydro-5-isopropyloxy-4,6,7-trimethylbenzofurane | 134867-31-5 | C16H24O3 |
| —— | (2R,3R)-2-(furan-2-yl)-4,4-dimethoxychroman-3-ol | 139936-44-0 | C15H16O5 |
| —— | (1R,3S)-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 | 1443020-79-8 | C31H38N2O7 |
| —— | 2-(RS)-(2-acetoxyethyl)-2,3-dihydro-5-benzyloxy-4,6,7-trimethylbenzofurane | 134867-32-6 | C22H26O4 |
| —— | 9-[2-(methylthio)phenyl]-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride | 1055878-80-2 | C16H17NOS*ClH |
| —— | 5,7-di-tert-butyl-3-(2-methyl-dihydrobenzofuran-5-yl)benzofuran-2-one | 1002760-52-2 | C25H30O3 |
| —— | Boc-Arg(Pbf)-CSNH2 | 1458012-06-0 | C24H39N5O5S2 |
| —— | 2,2-dimethyl-5-nitro-7-(2-chloro-ethoxy)-2,3-dihydro-benzofuran | 1089187-62-1 | C12H14ClNO4 |
| —— | (3-methyl-7-methylcarbamoyloxy-2-oxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-4-yl)-carbamic acid ethyl ester | 7678-08-2 | C14H17N3O6 |
| —— | 2-(RS)-(2-acetoxyethyl)-2,3-dihydro-5-acetoxy-4,6,7-trimethylbenzofurane | 134867-61-1 | C17H22O5 |
| —— | 2,3-dihydro-2,2-dimethyl-5-chloro-7-(3-chloro-propoxy)-benzofuran | 1089210-19-4 | C13H16Cl2O2 |
| —— | 5-(1-Chloro-2,2,2-trifluoro-1-m-tolyl-ethyl)-2,3-dihydro-benzofuran | 131543-77-6 | C17H14ClF3O |
| —— | 2-(5-Chloro-2,3-dihydro-2-oxo-3-phenyl-3-benzofuranyl)-1-[3-(3-methoxyphenyl)piperidyl]-1-oxoethane | 118708-97-7 | C28H26ClNO4 |
| —— | 4-(Trifluoromethyl)-2,3-dihydro-1-benzofuran | 1391292-15-1 | C9H7F3O |
| —— | 3-[5-benzyloxy-2,3-dihydro-2,2,4,6-tetramethylbenzo[b]furan-7-yl]propanal | 137418-50-9 | C22H26O3 |
| —— | (R)-6,7-Dichloro-2-(dichloro-phenylsulfanyl-methyl)-2,3-dihydro-benzofuran | 118166-42-0 | C15H10Cl4OS |
| —— | 2H-1,4-benzoxazine, 4-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-3,4-dihydro-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-8-[3-(trifluoromethoxy)phenyl]-, (3R)- | 956831-82-6 | C29H26F7NO5 |
| —— | 5,6-Dihydro-6,6-diphenyl-naphtho<2',3':2,3>pyran-4-ol | 5382-79-6 | C25H20O2 |
| —— | 3-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-propionic acid ethyl ester | 849761-81-5 | C23H28O3 |
| —— | 5,6-Dimethyl-2,3-dihydro-benzofuran-2-carboxylic acid | 1354950-79-0 | C11H12O3 |
| —— | (1S)-2-azido-1-[(2R)-5-fluoro-6-phenylmethoxy-3,4-dihydro-2H-chromen-2-yl]ethanol | 905454-80-0 | C18H18FN3O3 |
| —— | 1-{[3-(6-methyl-4H-chromen-3-yl)-1,2,4-oxadiazol-5-yl]methyl}piperidine | 1514898-77-1 | C18H21N3O2 |
| —— | (1S,2R)-2-aminomethyl-1-(2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid allyl-ethyl-amide | 947766-42-9 | C18H24N2O2 |
| —— | 7-chloro-2-chloromethyl-4,6-dimethyl-2,3-dihydro-furo[3,2-<i>c</i>]pyridine | 28667-66-5 | C10H11Cl2NO |
| —— | 7-((tert-butyldimethylsilyl)oxy)-4-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carbaldehyde | 892406-60-9 | C18H28O4Si |
| —— | 7-Bromo-5-methoxy-2,3-dihydro-1-benzofuran-3-ol | 1564844-06-9 | C9H9BrO3 |
| —— | (5-Bromo-2,3-dihydro-1-benzofuran-2-yl)methanamine hydrochloride | 883143-64-4 | C9H11BrClNO |
| —— | 8-(2,4,6-trichlorophenyl)-N,N-dipropyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridin-6-amine | 488125-79-7 | C23H27Cl3N2O |
| —— | (3S,4R)-3-isopropyl-8-methoxy-4-(nitromethyl)chroman-2-ol | 1260789-36-3 | C14H19NO5 |
| —— | ethyl 6,7-dichloro-2,3-dihydro-5-<3,5-bis<(chloroacetamido)methyl>-4-hydroxybenzyl>-2-benzofurancarboxylate | 95250-08-1 | C24H24Cl4N2O6 |
| —— | 2-Isopropyl-5-formyl-6-hydroxy-cumaran | 92847-78-4 | C12H14O3 |
| —— | cis-3-methyl-2,3,4,4a,5,6-hexahydro-1H-benzofuro<3,2-e>isoquinolin-7(7aH)-one | 85923-13-3 | C16H19NO2 |
| —— | 3-Hydroxyimino-1-benzofuran-6-ol | 7151-25-9 | C8H7NO3 |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-(4-fluorophenyl)amine | 852114-98-8 | C15H15FN2O |
| —— | 5-hydroxy-2-(2-phenylethyl)-6-(4-phenylbutyl)-2,3-dihydrobenzofuran | 138853-93-7 | C26H28O2 |
| —— | (R)-3-(1-(5-bromo-4-(5-chlorothiophen-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide | 1403883-30-6 | C16H10BrClF2N2O4S |
| —— | methyl 3-(4-bromophenyl)-2-cyano-2,3-dihydronaphtho[1,2-b]furan-2-carbimidate | 1613306-53-8 | C21H15BrN2O2 |
| —— | ethyl 2-cyano-3-(4-chlorophenyl)-2,3-dihydronaphtho[1,2-b]furan-2-carbimidate | 1613306-45-8 | C22H17ClN2O2 |
| —— | methyl 2-((2R,3S)-3,5-dimethyl-3-vinyl-2,3-dihydrobenzofuran-2-yl)acetate | 1393374-09-8 | C15H18O3 |