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 |
|---|---|---|---|
| —— | 1008117-16-5 | C27H22Cl2N4O4S | |
| —— | (4aS,9bR)-4-[1-(2-Amino-ethylamino)-meth-(Z)-ylidene]-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-3-one | 86658-11-9 | C17H20N2O2 |
| —— | 3-(2,3-dichlorophenyl)-4-(2,3-dihydro-1-benzofuran-7-ylmethyl)-4H-1,2,4-triazole | 936219-78-2 | C17H13Cl2N3O |
| —— | 2-(5-Chloro-2,3-dihydro-7-benzo[b]furanyl)-2-trimethylsiloxyethanenitrile | 82060-94-4 | C13H16ClNO2Si |
| —— | 3-hydroxy-2,2,3-trimethyl-2,3-dihydro-benzofuran-5-carboxylic acid | 104665-59-0 | C12H14O4 |
| —— | 4-[2-Cyanomethyl-4-oxo-chroman-(3Z)-ylidene]-4-hydroxy-butyric acid ethyl ester | 115085-94-4 | C17H17NO5 |
| —— | ethyl 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionate | 1005200-99-6 | C15H16N2O4 |
| —— | 3',5,5',7-tetramethyl-3-phenylbenzofuran-2(3H)-spiro-1'-cyclohex-2',5'-dien-4'-one | 76048-48-1 | C23H22O2 |
| —— | 2-(7-methoxy-2-methyl-2,3-dihydrobenzofuran-2-yl)acetonitrile | 1372769-20-4 | C12H13NO2 |
| —— | Ethyl Spiro<benzofuran-3(2H),1'-cyclopentane>-2-carboxylate | 86728-25-8 | C15H18O3 |
| —— | 2a,7b-Dihydro-7-methoxy-2a,7b-dimethyl-1,2-dioxeto<3,4-b>benzofuran | 128753-87-7 | C11H12O4 |
| —— | methyl ((3S)-7-bromo-5-chloro-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetate | 1452479-62-7 | C11H10BrClO4 |
| —— | 8-Chloro-2,2,9,9b-tetramethyl-2,3,4a,9b-tetrahydro-1H-dibenzofuran-4-one | 66613-76-1 | C16H19ClO2 |
| —— | 1-endo-phenyl-8b-methyl-6-amino-1,2-dihydrocyclobuto<c>benzopyran-3-one | 121262-31-5 | C18H17NO2 |
| —— | (S)-2,3-dihydro-benzofuran-4-carboxylic acid {1-[2-bromo-5-(3-trifluoromethyl-phenyl)-thiazole-4-carbonyl]-piperidin-2-ylmethyl}-amide | 1137129-61-3 | C26H23BrF3N3O3S |
| —— | (3S,3aR,8bR)-5,7-Dibromo-3,3a,6,8b-tetramethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan | 139126-15-1 | C15H18Br2O |
| —— | (R,E)-6-chloro-4-styryl-3,4-dihydrobenzo[e][1,2,3]oxathiazine 2,2-dioxide | 1393377-49-5 | C15H12ClNO3S |
| —— | 12-ethenyl-4,8-dimethyl-10-nitro-2-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-4-ol | 873425-99-1 | C16H15NO4 |
| —— | 4-(2-Hydroxy-2,3-dihydro-benzofuran-3-yl)-3,3-dimethyl-butyric acid methyl ester | 342817-71-4 | C15H20O4 |
| —— | ((2R<sup>*</sup>,3S<sup>*</sup>)-(+/-)-2,3-dihydro-2,3-dimethyl-3,4-dimethoxybenzo<b>furan-2-yl)hydroperoxide | 135831-61-7 | C12H16O5 |
| —— | 7-bromo-5-(2-bromomethyl-3-methyl-butyl)-4-methoxy-3-methyl-2,3-dihydro-benzofuran-6-ol | 51093-64-2 | C16H22Br2O3 |
| —— | (5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-cyclohexyl-methanol | 623176-25-0 | C17H23BrO2 |
| —— | Ta(OC6H3((CH3)3C)(CH3)2CH2)(OC6H3-2,6-((CH3)3C)2)Cl2 | 110433-63-1 | C28H41Cl2O2Ta |
| —— | 3-[(Z)-2-Hydroxy-phenylimino]-2,3-dihydro-benzofuran-2-carboxylic acid phenylamide | 122529-55-9 | C21H16N2O3 |
| —— | N-((3S)-1-(2-methyl-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-yl)cyclopropanecarboxamide | 1258851-47-6 | C17H22N2O2 |
| —— | 6-Bromo-hexanoic acid ((4R,9bS)-8,9b-dimethyl-3-oxo-1,2,3,4,4a,9b-hexahydro-dibenzofuran-4-yl)-amide | 58323-25-4 | C20H26BrNO3 |
| —— | (+/-)-N-methyl-1-[7-(2,5-difluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine | 852125-15-6 | C17H14F5NO |
| —— | 2-Acetyl-8-methoxy-5,6-dihydrobenzo<1,2-b:5,4-b'>difuran | 68454-38-6 | C13H12O4 |
| —— | (+/-)-{[7-(2,3-dimethylphenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-94-8 | C19H23NO2 |
| —— | 1-(2,3-Dihydro-1-benzofuran-6-yl)propan-2-amine hydrochloride | 1281872-58-9 | C11H16ClNO |
| —— | 3,3-dimethyl-7-t-butyl-2,3-dihydro-benzofuran-5-boronic acid | 623176-00-1 | C14H21BO3 |
| —— | 5-bromo-2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran | 1243544-98-0 | C13H16BrIO |
| —— | 4,6-difluoro-2,3-dihydro-1-benzofuran-3-amine hydrochloride | 1461713-34-7 | C8H7F2NO*ClH |
| —— | 4-Ethyl-5,6,7-trimethoxy-2-methyl-3-(3,4,5-trimethoxy-phenyl)-chroman-4-ol | 64554-45-6 | C24H32O8 |
| —— | 1-(4-methoxy-3-methyl-2,3-dihydro-benzofuran-6-yloxy)-3-methyl-butan-2-one | 68659-57-4 | C15H20O4 |
| —— | (+/-)-{[7-(2-methylphenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-91-5 | C18H21NO2 |
| —— | 2-Ethyl-6-methyl-cumaran | 91969-37-8 | C11H14O |
| —— | 5-chloro-2-[4-[7-fluoro-5-(1-propylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-2,3-dihydro-1-benzofuran-2-yl]piperidin-1-yl]pyrimidine | 1346529-41-6 | C25H30ClFN4O3S |
| —— | Ta{OC6H2-4-CH3-(CH3)3C(CH3)2CH2}2Cl | 110433-65-3 | C30H44ClO2Ta |
| —— | (2R,4S)-2-Butoxy-4-vinyl-chroman | 124313-25-3 | C15H20O2 |
| —— | (4aS,9bS)-2-Diethylaminomethyl-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-3-one | 68788-87-4 | C19H25NO2 |
| —— | 1196967-82-4 | C23H31N3O4S | |
| —— | 2-(1-Imidazolyl)methyl-2,3,7,8-tetrahydro-5,8,8-trimethyl-6H-furo[2,3-e]indol-7-one·hydrochloride | 170684-24-9 | C17H19N3O2*ClH |
| —— | [(3R,4aR,6aS,12aS,12bS)-9-[(2S,3R,4S)-3-acetyloxy-4-methylhexan-2-yl]-12a-hydroxy-11-methoxy-6a,12b-dimethyl-3-(2-trimethylsilyloxypropan-2-yl)-2,3,4a,5,6,12-hexahydro-1H-pyrano[3,2-a]xanthen-8-yl] acetate | 1255327-39-9 | C36H58O9Si |
| —— | cis-trans-2,3,5-Trimethylcumaran | 29654-65-7 | C11H14O |
| —— | (+/-)-{[5-methoxy-7-(3-thienyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-24-1 | C14H15NO2S |
| —— | N-((4R,9bS)-8,9b-Dimethyl-3-oxo-1,2,3,4,4a,9b-hexahydro-dibenzofuran-4-yl)-acetamide | 61132-79-4 | C16H19NO3 |
| —— | 6-tert-Butyl-2,2,9,9b-tetramethyl-2,3,4a,9b-tetrahydro-1H-dibenzofuran-4-one | 66613-74-9 | C20H28O2 |
| —— | 2,2,5-trimethyl-7a,8,9,10-tetrahydrocyclopenta<5,6>pyrano<4,3,2-de><3,1>benzoxathiin-4-ol | 133901-91-4 | C16H18O3S |
| —— | 4-Methoxy-3-methyl-5-(3-methyl-2-methylene-butyl)-2,3-dihydro-benzofuran-6-ol | 68659-58-5 | C16H22O3 |