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-(2,3-Dihydro-2-benzofuranyl)ethanone oxime | 19863-71-9 | C10H11NO2 |
| —— | 7-chloro-6,8,9<i>c</i>-trimethyl-(3a<i>r</i>)-1,2,3,3a-tetrahydro-9<i>H</i>-benzo[<i>e</i>]pyrrolo[2,1-<i>b</i>][1,3]oxazine | 71582-64-4 | C14H18ClNO |
| —— | 936563-53-0 | C17H15ClO3 | |
| —— | 6,7-Dichloro-5-(2-cyclopropylthiocarbamoyl-acetyl)-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester | 126200-58-6 | C17H17Cl2NO4S |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-[(1-ethylpropyl)thio]-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-34-7 | C22H25Cl2NOS |
| —— | 3,3-dimethyl-7-(2,2-dimethyl-propyl)-5-[(1S,2S)-3-hydroxy-1,2-methano-1-methyl-propyl]-2,3-dihydro-benzofuran | 623176-11-4 | C20H30O2 |
| —— | 5-(2,3-dihydro-1-benzofuran-5-yl)-1H-pyrazole-3-carboxylic acid | 1491131-49-7 | C12H10N2O3 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-N,N-diethyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488125-91-3 | C21H23Cl3N2O |
| —— | 4-(2,3-dihydro-benzofuran-6-yl)-4-hydroxy-cyclohexanone | 1252615-64-7 | C14H16O3 |
| —— | (3aS)-3c,5a,5b-trimethyl-7t,8-diphenyl-(3ar,5ac,5bt,6ac,9ac,9bcC5a,9ct)-decahydro-furo[3''',2''':5'',6'']benzo[1'',2'':1',3']cyclopropa[1',2':3,4]cyclopenta[1,2-d]isoxazole-2,6-dione | 17603-79-1 | C28H29NO4 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-N,N-dicyclohexyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488126-01-8 | C29H36Cl2N2O |
| —— | (4aS,9bR)-8-(2,6-difluoro-4-chlorophenyl)-6-methoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-75-6 | C18H16ClF2NO2 |
| —— | (1S,3S)-3-[([(S)-1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclopentanecarboxylic acid | 1443020-86-7 | C31H38N2O7 |
| —— | (4aS,9bR)-8-(2,6-difluoro-4-chlorophenyl)-6-propoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-77-8 | C20H20ClF2NO2 |
| —— | 5-(benzyloxy)-2,3-dihydro-2-(2-phenethyl)-6-<3-(4-pyridylthio)propyl>benzofuran | 139201-51-7 | C31H31NO2S |
| —— | 5<6,7-dichloro-2,3-dihydro-5-(2-thienylcarbonyl)-2-bezofuranyl>-1H-tetrazole | 77886-71-6 | C14H8Cl2N4O2S |
| —— | 1334058-81-9 | C20H26N2O4S | |
| —— | 2,3-dihydro-4,5-dihydroxy-2-methylbenzofuran | 109073-06-5 | C9H10O3 |
| —— | 5-butyl-4-(1-phenylvinyl)-2,3-dihydrobenzofuran | 1638140-28-9 | C20H22O |
| —— | (+)-(3R)-7-Methoxy-2,3-dihydrobenzo<b>furan-3-essigsaeure | 84985-56-8 | C11H12O4 |
| —— | S-3-<2,3-Dihydro-7-hydroxy-2-(1-hydroxy-1-methylethyl)-6-methoxy-5-benzofuranyl>-1-propanol diacetate | 78796-63-1 | C19H26O7 |
| —— | 4-(2-chlorobenzylidene)-2,2-dimethyl-7-(2-methylbut-3-yn-2-yloxy)-3,4-dihydro-2H-chromene | 1038917-75-7 | C23H23ClO2 |
| —— | (+/-)-5-acetyloxy-2,3-dihydro-4,6,7-trimethyl-2-benzofuranethanamine | 154954-42-4 | C15H21NO3 |
| —— | 2,2,5-trinitro-2,3-dihydrobenzofuran | 1541175-13-6 | C8H5N3O7 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-methoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-66-5 | C18H16Cl3NO2 |
| —— | 3,4-dibromo-chroman-3-carboxylic acid methyl ester | 36044-50-5 | C11H10Br2O3 |
| —— | 3-Chlormercury-2,5-dimethyl-2,3-4H-benzopyran | 66865-72-3 | C11H13ClHgO |
| —— | 1-benzylidene-3,3a-dihydro-9-methoxy-1H-furo<3,4-b><1>benzopyran | 111570-56-0 | C19H16O3 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-phenyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-18-7 | C23H18Cl3NO |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid {3-[2-dimethylamino-5-(2-fluoro-phenyl)-thiazole-4-carbonyl]-thiazolidin-2-ylmethyl}-amide | 1204585-46-5 | C25H25FN4O3S2 |
| —— | Sodium; 6,7-dichloro-5-((E)-3-methylsulfanyl-3-morpholin-4-yl-acryloyl)-2,3-dihydro-benzofuran-2-carboxylate | 126201-13-6 | C17H16Cl2NO5S*Na |
| —— | 7-bromo-6,8,9<i>c</i>-trimethyl-(3a<i>r</i>)-1,2,3,3a-tetrahydro-9<i>H</i>-benzo[<i>e</i>]pyrrolo[2,1-<i>b</i>][1,3]oxazine | 71582-63-3 | C14H18BrNO |
| —— | 4-(2-propyl-2,3-dihydrobenzofuran-5-yl)phenol | 1394958-23-6 | C17H18O2 |
| —— | 2-(1-Chlormercuryethanol)-5-methyl-2,3-dihydrobenzofuran | 66865-71-2 | C11H13ClHgO |
| —— | 4-ethyl-3-phenyl-chroman-4-ol | 33103-12-7 | C17H18O2 |
| —— | 6,7-Dihydro-7-phenyldibenz<b,d>oxepin-7-ol | 32543-84-3 | C20H16O2 |
| —— | 2-(2,4-dichlorophenoxy)-N-(6-fluoro-2,3-dihydro-1-benzofuran-3-yl)propanamide | 1418283-26-7 | C17H14Cl2FNO3 |
| —— | (+/-)-{[7-(5-chloro-2-methoxyphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-56-2 | C17H17ClFNO2 |
| —— | 7-t-butyl-3-phenyldihydrobenzofuran | 134268-04-5 | C18H20O |
| —— | 4,6-dimethyl-7a,8,9,10,11,12-hexahydro-15H-azepino[2',1':2,3]oxazolo[4,5-b]phenoxazine-1,14-dicarboxylic acid dimethyl ester | 7485-37-2 | C24H26N2O6 |
| —— | 6-(3-Phenoxy-propyl)-2,3-dihydro-benzofuran-3,5-diol | 139201-66-4 | C17H18O4 |
| —— | 2,3-dihydro-6-<4-(methylthio)benzyl>-2-(2-phenylethyl)-5-benzofuranol | 139201-60-8 | C24H24O2S |
| —— | 7-ethoxy-8-fluoro-3-(4-pentylphenyl)hydrocoumarin | 940949-01-9 | C22H25FO3 |
| —— | 6,7-Dichloro-5-{2-[5-methyl-3H-thiazol-(2E)-ylidene]-acetyl}-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester | 126201-10-3 | C17H15Cl2NO4S |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-phenyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-09-6 | C23H19Cl2NO |
| —— | 5-[1-[4-(trifluoromethyl)phenyl]ethylidene]-2,3-dihydro-1-benzofuran-1-ium | 86766-86-1 | C17H14F3O |
| —— | 5-[4-(5-decylpyrimidine-2-yl)phenyl]-2-octylcoumaran | 160310-77-0 | C36H50N2O |
| —— | 2a,7b-Dihydro-2a,7b-dimethyl-1,2-dioxeto<3,4-b>benzofuran | 33973-15-8 | C10H10O3 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-N-methyl-N-ethyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488125-93-5 | C20H22Cl2N2O |
| —— | (2R,3R)-5-Chloro-3-(2-hydroxy-ethyl)-2,3-dihydro-benzofuran-2-carboxylic acid | 70554-72-2 | C11H11ClO4 |