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 |
|---|---|---|---|
| —— | 9-Methyl-11-oxo-8,10,12-trioxa-tricyclo[7.2.1.0<sup>2,7</sup>]dodeca-2(7),3,5-triene-1-carboxylic acid methyl ester | 60779-23-9 | C12H10O6 |
| —— | ethyl 5-<3,3-bis(4-methoxybenzyl)-2-propenoyl>-6,7-dichloro-2,3-dihydro-2-benzo<b>furancarboxylate | 126200-53-1 | C30H28Cl2O6S2 |
| —— | 3,3,4-trifluoro-4-trifluoromethyl-chroman | 56595-71-2 | C10H6F6O |
| —— | tetrahydrodimethoxyarthrographol | 138258-60-3 | C15H22O3 |
| —— | 4-(2-fluoro-6,7,8,9,10,10a-hexahydro-5aH-benzo[b]cyclohepta[d]-furan-10a-yl)phenol | 1147714-41-7 | C19H19FO2 |
| —— | 877120-50-8 | C74H96O10 | |
| —— | 10-methyl-5-phenyl-3-deutero-3,4,5,6-tetrahydro-2H-benzo[b]oxocine | 1344714-09-5 | C18H20O |
| —— | (-)-5-hydroxy-2,3-dihydro-N-methyl-N-propyl-3-benzofuranmethylamine, oxalate | 118610-75-6 | C2H2O4*C13H19NO2 |
| —— | (4,6-ditert-butyl-2,2-dioctyl-3H-1-benzofuran-5-yl) acetate | 1027300-28-2 | C34H58O3 |
| —— | (4aS,9bR)-4-[1-Butylamino-meth-(Z)-ylidene]-8,9b-dimethyl-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one | 86658-20-0 | C19H25NO2 |
| —— | 1,6-Dichlor-4b,9b-dimethyl-4b,9b-dihydro-benzofuro<3,2-b>benzofuran | 3988-23-6 | C16H12Cl2O2 |
| —— | (S)-3,3,4-Trifluoro-2,2-dimethyl-4-trifluoromethyl-chroman | 56595-74-5 | C12H10F6O |
| —— | pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydro-benzofuran-6-ylmethyl)-amide] 6-[4-(1-methyl-piperidin-3-yloxy)-benzylamide] | 691002-42-3 | C28H31N5O4 |
| —— | 2,4,7-Trimethyl-3-chromanone-4-acetaldehyde | 74552-39-9 | C14H16O3 |
| —— | 4-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid | 1895984-35-6 | C9H7BrO3 |
| —— | (+/-)-{[7-(2,3-difluorophenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-26-3 | C16H15F2NO2 |
| —— | (R/S)-2-(N-Boc-aminomethyl)-2,3-dihydrobenzofuran-5-ylamine | 944447-72-7 | C14H20N2O3 |
| —— | 2-(1-hydroxy-1-methyl-ethyl)-5-iodo-2,3-dihydro-benzofuran-6-ol | 1155310-14-7 | C11H13IO3 |
| —— | (+/-)-(7-bromo-5-cyclopentyl-2,3-dihydro-1-benzofuran-2-yl)methanol | 852116-84-8 | C14H17BrO2 |
| —— | N-benzyl-3-(3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine | 820259-41-4 | C25H27NO2 |
| —— | (4aS,9bR)-4-[1-Dibenzylamino-meth-(E)-ylidene]-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-3-one | 86657-83-2 | C29H27NO2 |
| —— | 3-hydroxy-6-methyl-3-phenylbenzo<b>-2(3H)-furanone | 92545-52-3 | C15H12O3 |
| —— | 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (dipropylaminosulfenyl)(methyl)carbamate | 55285-07-9 | C18H28N2O3S |
| —— | 4-(7-chloro-2,2-dimethyl-2,3-dihydro-benzofuran-5-yl)-4-oxo-but-2-enoic acid | 57899-07-7 | C14H13ClO4 |
| —— | (3Z)-3-[(4-chlorophenyl)methylidene]-6-methoxy-1-(trifluoromethyl)-1H-2-benzofuran | 1569046-67-8 | C17H12ClF3O2 |
| —— | 6-hexyl-6-methyldibenzo[d,f][1,3]dioxepine | 1042724-23-1 | C20H24O2 |
| —— | (4aS,9bR)-4-[1-Hydroxy-meth-(Z)-ylidene]-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-3-one | 86658-05-1 | C15H14O3 |
| —— | 3-Hydroxy-5-methylthio-2-methyl-2,3-dihydrobenzo<b>furan | 60770-59-4 | C10H12O2S |
| —— | 4-Methylsulfonyl-2,3-dihydro-1-benzofuran-6-amine | 1335496-52-0 | C9H11NO3S |
| —— | methyl [2-(5-methoxy-2,3-dihydro-benzofuran-3-yl)-ethyl]-carbamate | 1148035-95-3 | C13H17NO4 |
| —— | 7-t-Butyl-5-methyl-3-phenylbenzofuran-2(3H)-on | 66737-85-7 | C19H20O2 |
| —— | N-(3-(piperidin-1-yl)propyl)-2,3-dihydrobenzofuran-5-carboxamide | 875711-28-7 | C17H24N2O2 |
| —— | (+/-)-{[5-(trifluoromethyl)-7-(4-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-79-3 | C16H13ClF3NO |
| —— | 1,2,3,4-tetrachloro-5a,10b-dihydro-benzo[<i>b</i>]benzofuro[2,3-<i>e</i>][1,4]dioxin | 23675-07-2 | C14H6Cl4O3 |
| —— | N-{1-[((S)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-2-oxo-1,2-dihydro-pyridin-3-yl}-3-phenyl-propionamide | 195071-95-5 | C27H27N3O6 |
| —— | (+/-)-{[7-(2,4-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-51-1 | C16H15Cl2NO |
| —— | N-benzyl-3-(4-isopropylphenyl)-6,7-dimethyl-2,3-dihydro-1-benzofuran-5-amine | 820257-37-2 | C26H29NO |
| —— | ethyl 2-trifluoromethanesulfonyloxymethyl-2,3-dihydrobenzofuran-5-carboxylate | 197506-28-8 | C13H13F3O6S |
| —— | 1-(2,3-dihydro-benzofuran-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one | 1260006-08-3 | C17H17N3O2 |
| —— | 7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine | 820260-07-9 | C21H25NO2 |
| —— | (2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one O-(4-(chloromethyl)-2,5-dimethylbenzyl) oxime | 1076247-26-1 | C33H34ClNO6 |
| —— | 3-Methoxy-2,3-dihydro-benzofuran-2-ol | 71956-53-1 | C9H10O3 |
| —— | (4S)-4-phenyl-2-oxatricyclo[6.3.1.04,12]dodeca-1(11),8(12),9-trien-6-one | 1415357-77-5 | C17H14O2 |
| —— | N-[2-(5-methoxy-2,3-dihydro-benzofuran-3-yl)-ethyl]-butyramide | 1148035-91-9 | C15H21NO3 |
| —— | 13,17-Dimethyl-6-(4-methylpiperazin-1-yl)-8-oxa-2,13,17,21,23,25-hexazatetracyclo[17.6.1.13,7.022,26]heptacosa-1(25),3(27),4,6,19,22(26),23-heptaen-12-one | 1111233-43-2 | C27H38N8O2 |
| —— | cis-1,1',1'',1'''-(((3,10-di-tert-butyl-5,5a,6,7,7a,8-hexahydrocyclopenta[1,2-b:1,5-b']dichromene-1,12-diyl)bis(oxy))bis(phosphinetriyl))tetrakis(1H-pyrrole) | 1442637-42-4 | C43H48N4O4P2 |
| —— | 4-(1',2',3',5',6',8',9',9a'-octahydro-3H-spiro[benzofuran-2,7'-pyrrolo[1,2-a]azepin]-5-yl)benzonitrile | 1258430-74-8 | C23H24N2O |
| —— | 2-chloro-4-(2,3-dihydro-1-benzofuran-7-yl)-5-fluoropyrimidine | 1427316-21-9 | C12H8ClFN2O |
| —— | (2R,3R)-6-chloro-2-(furan-2-yl)-4,4-dimethoxychroman-3-ol | 139936-45-1 | C15H15ClO5 |
| —— | (+/-)-{[7-(2,3-difluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-83-9 | C16H12F5NO |