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 |
|---|---|---|---|
| —— | pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydro-benzofuran-5-ylmethyl)-amide] 6-[4-(thiomorpholine-4-carbonyl)-benzylamide] | 691002-23-0 | C27H27N5O4S |
| —— | (R)-methyl 3-(4-bromophenyl)-5-((S)-(4-methoxyphenyl)((S)-2-oxo-3-phenyl-2,3-dihydrobenzofuran-3-yl)methyl)-4,5-dihydroisoxazole-5-carboxylate | 1417999-35-9 | C33H26BrNO6 |
| —— | 3,4-Dibrom-8-methoxy-2,2-dimethylchroman | 13217-76-0 | C12H14Br2O2 |
| —— | (R)-3,5-dimethyl-7-(trifluoromethoxy)-2,3-dihydro-1,4-benzoxazepine | 1345731-92-1 | C12H12F3NO2 |
| —— | 6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-carboxylic acid | 1452478-16-8 | C16H12Cl2O4 |
| —— | N-(2,3-dihydro-1-benzofuran-5-ylmethyl)cyclopentanamine | 1157544-58-5 | C14H19NO |
| —— | (R)-methyl 3-(4-bromophenyl)-5-((S)-(4-bromophenyl)((S)-2-oxo-3-phenyl-2,3-dihydrobenzofuran-3-yl)methyl)-4,5-dihydroisoxazole-5-carboxylate | 1417999-37-1 | C32H23Br2NO5 |
| —— | 4-[(1R,2R,3aS,8bS)-2-Hydroxy-1-((E)-(3R,4R)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester | 274250-76-9 | C25H32O5 |
| —— | 2-Acetoxy-spiro<benzofuran-3(2H),1'-cyclopentane> | 86728-27-0 | C14H16O3 |
| —— | 1402160-62-6 | C17H14O2 | |
| —— | Ethofumesate | 68505-68-0 | C11H14O4S |
| —— | (2R,3S)-3-Methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid | 2752192-48-4 | C10H10O3 |
| —— | 1239588-41-0 | C21H28O3 | |
| —— | (3S,4aS,9bR)-6-Methoxy-9b-(2-methylamino-ethyl)-1,2,3,4,4a,9b-hexahydro-dibenzofuran-3-ol | 78167-05-2 | C16H23NO3 |
| —— | 2-(difluoromethyl)-3,4-dihydro-2H-1-benzopyran-3-carboxylic acid, Mixture of diastereomers | 2137958-08-6 | C11H10F2O3 |
| —— | (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{2-[4-(2-{[3-(isopropylthio)benzyl]oxy}ethoxy)phenyl]ethyl}-1,3-oxazolidin-2-one | 620600-79-5 | C33H39NO6S |
| —— | 8-methoxy-4-(2-nitroethenyl)-2,3,5,6-tetrahydrofuro[3,2-f][1]benzofuran | 194787-75-2 | C13H13NO5 |
| —— | 4-[(1R,2R,3aS,8bS)-2-Acetoxy-1-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl]-butyric acid methyl ester | 274250-86-1 | C27H34O6 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(3-methyl-1H-pyrazol-1-yl)-acetamide | 1048959-52-9 | C23H32N4O2 |
| —— | cis-2-Brommethyl-4-phenyl-chroman-carbonsaeure-(4)-methylester | 93809-10-0 | C18H17BrO3 |
| —— | 3-Phenyl-2,3-dihydro-benzofuran-3-carbonsaeure-<4-dimethylamin-propin-(2)-yl>-ester | 100996-32-5 | C21H21NO3 |
| —— | 2-[[dichloro-(4-methoxyphenyl)-λ4-tellanyl]methyl]-7-methyl-2,3-dihydro-1-benzofuran | 115022-83-8 | C17H18Cl2O2Te |
| —— | 1239588-40-9 | C18H24O3 | |
| —— | trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{3-methyl-4-[2-(3-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-ethoxy]-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid | 1443020-36-7 | C33H41N3O6 |
| —— | (1S,2R,3aS,9aR)-5-Methoxy-2-methoxymethoxy-2,3,3a,9a-tetrahydro-1H-benzo[b]cyclopenta[e][1,4]dioxin-1-ol | 120888-17-7 | C14H18O6 |
| —— | Dihydroxo-<4-formyl-phenylendioxo-(1.2)>-borat-anion | 23054-15-1 | C7H6BO5 |
| —— | (4aS,9bR)-8,9b-Dimethyl-4-[1-piperazin-1-yl-meth-(E)-ylidene]-4a,9b-dihydro-4H-dibenzofuran-3-one | 86657-89-8 | C19H22N2O2 |
| —— | (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester | 760979-78-0 | C42H58BNO8Si |
| —— | 5-(4-(2,3-dihydrobenzofuran-3-yloxy)phenyl)-3-(methoxymethoxy)isoxazole | 1294452-75-7 | C19H17NO5 |
| —— | 2-propyl-2,3-dihydrobenzofuran-4-amine | 1258851-16-9 | C11H15NO |
| —— | Tributyl-(2,3-dihydro-benzofuran-5-yl)-stannane | 223432-28-8 | C20H34OSn |
| —— | (4E,4aS,9bR)-4-(diethylaminomethylidene)-8,9b-dimethyl-2,4a-dihydro-1H-dibenzofuran-3-one | 86657-93-4 | C19H25NO2 |
| —— | 3,4,4a,9b-Tetrahydro-8,9b-dimethyl-dibenzofuranon-3-methylnitron | 86658-32-4 | C15H17NO2 |
| —— | 1-((2R,3R,4R)-6,8-dichloro-2-methyl-4-(nitromethyl)chroman-3-yl)propan-1-one | 1627214-19-0 | C14H15Cl2NO4 |
| —— | 2,5-Dimethyl-3-(p-cyanphenyl)-cumaran | 93315-22-1 | C17H15NO |
| —— | 2-(1-azidoethyl)-6-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-1-benzofuran | 1224718-87-9 | C20H19N3O2 |
| —— | 3-methyl-PPBF | 850480-92-1 | C20H24O4S |
| —— | 5-Chloro-3,3-difluoro-6-iodo-2,4-dihydrochromene | 1154740-82-5 | C9H6ClF2IO |
| —— | [Ba((μ-dbbfo)2Al(CH3)2)2] | 862158-67-6 | C44H56Al2BaO8 |
| —— | 2-[4-[(6-Chloro-1,2,3,4-tetrahydro-[1]benzofuro[3,2-c]pyridin-8-yl)sulfonyl]phenyl]propan-2-ol;hydrochloride | 1387001-06-0 | C20H20ClNO4S*ClH |
| —— | 3,4-dihydro-6-(phenylmethoxy)-2H-1-benzopyran-2-carboxaldehyde | 99199-83-4 | C17H16O3 |
| —— | methyl 4-((1R,2R,3aS,8bS)-2-hydroxy-1-((3S,4S,E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl)butanoate | 274250-66-7 | C25H32O5 |
| —— | (+-)-8,9b-dimethyl-(4ar.9bc)-1,2,3,4,4a,9b-hexahydro-dibenzofuran-3ξ-ol | 108125-41-3 | C14H18O2 |
| —— | hydroxy-4α methoxymethylenoxy-6 formylmethyl-9bβ hexahydrodibenzofuranne | 117570-28-2 | C16H20O5 |
| —— | 2,5a,9-Trimethyl-5a,10b-dihydro-2,3b-benzofuro-benzofuran-carbonsaeure-(10b) | 25653-57-0 | C18H16O4 |
| —— | 3-(3-chloro-1-propyl)-2,3-dihydro-5-fluoro-benzofuran | 147373-17-9 | C11H12ClFO |
| —— | 3-ethyl 4-methyl 2-chloro-5-hydroxy-2-(trifluoromethyl)-2,3-dihydrobenzo[b]oxepine-3,4-dicarboxylate | 1354633-00-3 | C16H14ClF3O6 |
| —— | (4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl azide | 1072073-87-0 | C15H13N3O |
| —— | (E)-5-methoxy-4-(1-propenyl)-2,3-dihydrobenzofuran | 130933-06-1 | C12H14O2 |
| —— | 6a-Piperazino-3a-phenyl-2,3,3a,6a-tetrahydro-4,5-benzofuro<2,3-b>furan | 106322-37-6 | C20H22N2O2 |