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 |
|---|---|---|---|
| —— | 6,7-Dichloro-5-{2-[4-methoxy-thiazolidin-(2E)-ylidene]-acetyl}-2,3-dihydro-benzofuran-2-carboxylic acid tert-butyl ester | 126200-82-6 | C19H21Cl2NO5S |
| —— | 3a-acetoxy-4-(benzyloxy)-6-methoxy-3a,8a-dihydrofuro<2,3-b>benzofuran | 78596-83-5 | C20H18O6 |
| —— | 1-(5-methyl-2,3-dihydro-benzofuran-7-yl)-propan-1-one semicarbazone | 106377-76-8 | C13H17N3O2 |
| —— | (3R,4R,5E,8S,9E,11E)-12-(9,9-di-tert-butyl-1-((R)-4-hydroxy-3-methylbutyl)-4,8,10-trioxa-9-silacyclohepta[def]fluoren-6-yl)-3,8-dimethyltrideca-5,9,11-trien-4-ol | 1443650-57-4 | C40H58O5Si |
| —— | O-Ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-7-benzofuranyl)dithiophosphate | 96408-30-9 | C15H23O3PS2 |
| —— | ((4S,5S)-5-{[Bis-(4-methoxy-benzyl)-amino]-methyl}-2-isopropyl-2-methyl-[1,3]dioxolan-4-ylmethyl)-bis-(4-methoxy-benzyl)-amine | 515870-99-2 | C41H52N2O6 |
| —— | (2R<sup>*</sup>,3R<sup>*</sup>,6R<sup>*</sup>)-2,6,9-trimethyl-3,4,5,6-tetrahydro-2,6-methano-2H-1-benzoxocin-3-yl acetate | 145382-82-7 | C17H22O3 |
| —— | 8-(2,4,6-trichlorophenyl)-6-ethoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine | 488125-46-8 | C19H18Cl3NO2 |
| —— | 2-fluoro-8-((5-iodo-2,3-dihydrobenzofuran-6-yl)methyl)-9H-purin-6-amine | 1289544-61-1 | C14H11FIN5O |
| —— | 2,3-dihydro-7-iodo-5-nitrobenzofuran | 181633-35-2 | C8H6INO3 |
| —— | 4-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)butanoic acid | 1234843-58-3 | C21H23ClO4 |
| —— | 2-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-3-fluorophenyl)cyclopropanecarboxylic acid | 1234843-75-4 | C21H20ClFO4 |
| —— | (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-N-(2,3,5,6-tetraethylbenzyl)-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925440-01-3 | C32H37NO7 |
| —— | 3-({(2,3-dihydro-1-benzofuran-7-ylcarbonyl)[1-(4-fluorophenyl)ethyl]amino}methyl)benzoic acid | 1398583-51-1 | C25H22FNO4 |
| —— | 2,4,5a,7,9-Pentamethyl-5a,10b-dihydro-2,3b-benzofuro-benzofuran-carbonsaeure-(10b) | 25653-59-2 | C20H20O4 |
| —— | (+/-)-4a,8-dimethyl-(4a<i>r</i>,9b<i>c</i>)-3,4,4a,9b-tetrahydro-1<i>H</i>-dibenzofuran-2-one semicarbazone | 108170-94-1 | C15H19N3O2 |
| —— | (+/-)-2-(azidomethyl)-7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran | 1072073-46-1 | C15H11Cl2N3O |
| —— | (2R,3R)-5-Chloro-3-methoxycarbonylmethyl-2,3-dihydro-benzofuran-2-carboxylic acid | 70554-69-7 | C12H11ClO5 |
| —— | 7-bromo-5-hydroxy-4-nitro-2-(2-oxoethyl)-2,3-dihydrobenzo[b]furan | 197578-58-8 | C10H8BrNO5 |
| —— | 2,3-Dihydro-benzofuran-2-carboxylic acid [4-(4-bromo-phenyl)-thiazol-2-yl]-amide | 15864-15-0 | C18H13BrN2O2S |
| —— | 3-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-2,3-difluorophenyl)propanoic acid | 1352739-86-6 | C20H19ClF2O4 |
| —— | 2-(2-(4-((5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)cyclopropyl)acetic acid | 1234843-99-2 | C22H23FO4 |
| —— | (+/-)-2-(azidomethyl)-5-chloro-7-(3-methylphenyl)-2,3-dihydro-1-benzofuran | 852111-41-2 | C16H14ClN3O |
| —— | (R)-6-(t-butyldimethylsilyloxy)-2-isopropenyl-4-hydroxy-2,3-dihydrobenzofuran-5-carbaldehyde | 1058196-63-6 | C18H26O4Si |
| —— | 1,1,-diphenyl-3,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrophenanthrene | 136197-36-9 | C26H22O2 |
| —— | [Al(2,2'-ethylidenebis(4,6-di-tert-butylphenolato))(μ-OPr-i)]2 | 271779-90-9 | C66H102Al2O6 |
| —— | 3-(3,4-dihydro-3-dimethylhydroxymethyl-5-methoxybenzofuran)-cis-2-propenoic acid | 110202-88-5 | C15H18O5 |
| —— | 4-(6-methylpyridin-3-yl)-N-(2-octyl-2,3-dihydrobenzofuran-6-yl)thiazol-2-amine | 1088697-28-2 | C25H31N3OS |
| —— | 2H,3H-3-((trimethylsilyl)methylene)benzofuran | 130013-43-3 | C12H16OSi |
| —— | 2,9-dimethoxy-(5ar,10bc)-5a,10b-dihydrobenzo<b>benzo<4,5>furo<3,2-d>furan | 124483-05-2 | C16H14O4 |
| —— | 1-(4,7-dimethoxy-6-((4-methoxybenzyl)oxy)-2,3-dihydrobenzofuran-5-yl)ethan-1-one | 1025008-53-0 | C20H22O6 |
| —— | DL-4-Acetoxy-2-(1-acetoxy-isopropyl)-cumaran | 101103-33-7 | C15H18O5 |
| —— | (+/-)-3-Hydroxy-2,3-dihydro-benzofuran-2,2,5-tricarbonsaeure-2,2-diethylester-5-methylester | 94429-43-3 | C16H18O8 |
| —— | 2-((4-((5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)thio)-acetic acid | 1234842-18-2 | C19H19FO4S |
| —— | (trans)-N-methoxy-N-methyl-3-(2,3-dihydro-benzofuran-7-yl)propenamide | 209256-84-8 | C13H15NO3 |
| —— | 3-(4-(dideuterio(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-3-fluoro-2-propylphenyl)propanoic acid | 1234844-45-1 | C23H26ClFO4 |
| —— | 1-(4-hydroxy-6-methoxy-4H-chromen-3-yl)ethan-1-one | 1642135-77-0 | C12H12O4 |
| —— | 2,2-dimethyl-5-nitro-7-(3-bromo-propoxy)-2,3-dihydro-benzofuran | 1089187-66-5 | C13H16BrNO4 |
| —— | 3,4-dibenzo-2,8-dioxabicyclo<3.3.0>oct-6-ene | 84521-78-8 | C10H8O2 |
| —— | 2-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-3,5-difluorobenzyl)cyclopropanecarboxylic acid | 1234843-79-8 | C22H21ClF2O4 |
| —— | 6-(3-hydroxypropyl)-3,4-dihydro-2,2-dimethyl-3-iodo-2H-1-benzopyran | 410087-97-7 | C14H19IO2 |
| —— | ethyl 2-((2S,3R,4S)-6-chloro-4-((2-hydroxyphenyl)amino)-3-methyl-3-nitrochroman-2-yl)acetate | 1266339-56-3 | C20H21ClN2O6 |
| —— | 4-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)-2-methylbutanoic acid | 1234843-62-9 | C22H25ClO4 |
| —— | (8bS,14bS)-13-Methyl-8b,14b-dihydro-10-oxa-benzo[g]chrysen-9-one | 81009-12-3 | C22H16O2 |
| —— | 5.5'-Dimethyl-cumarano-3'.2'.2.3-cumaran | 10410-58-9 | C16H14O2 |
| —— | (4R)-7-chloro-2-(fluoromethyl)-2-methylchroman-4-amine | 1221638-79-4 | C11H13ClFNO |
| —— | Methyl (2-hydroxymethyl-2,3-dihydro-7-fluorobenzo[b]furan-5yl)acetate | 129703-92-0 | C12H13FO4 |
| —— | 3,3-dimethyl-7-hexyl-5-[(1S,2S)-1,2-methano-1-methyl-3-oxo-propyl]-2,3-dihydro-benzofuran | 623176-40-9 | C21H30O2 |
| —— | (5-fluoro-7-formyl-2,3-dihydrobenzofuran-2-yl)methyl acetate | 1352740-43-2 | C12H11FO4 |
| —— | (5-fluoro-2-methyl-2,3-dihydrobenzofuran-2-yl)methanol | 1352740-37-4 | C10H11FO2 |