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 |
|---|---|---|---|
| —— | 2,4,7,9-tetrachloro-5a,10b-dimethyl-5a,10b-dihydro-benzo[<i>b</i>]benzo[4,5]furo[3,2-<i>d</i>]furan | 67238-36-2 | C16H10Cl4O2 |
| —— | 2,3-dihydro-3,3-dimethyl-2-methylcarbonyloxybenzofuran-5-yl dimethylaminosulfonate | 57253-68-6 | C14H19NO6S |
| —— | (+/-)-{[7-(3-chlorophenyl)-5-phenyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852120-11-7 | C22H20ClNO |
| —— | 1239588-39-6 | C22H34O2Si | |
| —— | (R)-methyl 3-(4-bromophenyl)-5-((S)-((S)-3-(4-bromophenyl)-2-oxo-2,3-dihydrobenzofuran-3-yl)(phenyl)methyl)-4,5-dihydroisoxazole-5-carboxylate | 1417999-30-4 | C32H23Br2NO5 |
| —— | 2-(2-acetoxyethyl)-2,3-dihydrobenzofuran | 74133-38-3 | C12H14O3 |
| —— | [5-Methoxy-benzofuran-(3E)-ylidene]-acetonitrile | 39581-43-6 | C11H9NO2 |
| —— | 2,3-dihydro-1-benzofuran-5-yl-ethoxymethanimine | 1019018-81-5 | C11H13NO2 |
| —— | 8,9b-Dimethyl-3-<1>piperidyl-4a,9b-dihydro-dibenzofuran | 31704-68-4 | C19H23NO |
| —— | 6,8-Dinitro-1,2,3,3a,8b-pentahydro-cyclopenta<b>benzofuran | 94784-64-2 | C11H10N2O5 |
| —— | 87901-54-0 | C16H15O | |
| —— | 2.3-Dihydro-2-piperidino-3-<2-methyl-propyl>-5-hydroxybenzofuran | 7196-02-3 | C17H25NO2 |
| —— | (+/-)-[4,5-difluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide | 852111-75-2 | C16H13F2N3O |
| —— | 1,13-diethoxy-5a,6,7,8,8a,9-hexahydro-5H-chromeno[3,2-d]xanthene | 1569792-08-0 | C24H28O4 |
| —— | 2-Bromacetyl-5-nitro-2,3-dihydrobenzo<b>furan-2-carbonsaeureethylester | 109831-25-6 | C13H12BrNO6 |
| —— | diethyl 2,3-dihydro-1-benzofuran-3-ylmalonate | 1569356-44-0 | C15H18O5 |
| —— | (+/-)-2-(azidomethyl)-7-methoxy-2,3-dihydro-1-benzofuran | 1072073-00-7 | C10H11N3O2 |
| —— | trans-4-({{3-chloro-4-[3-(2,5-dioxo-pyrrolidin-1-yl)-propyl]-benzyl}-[1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-amino}-methyl)-cyclohexanecarboxylic acid | 1443020-24-3 | C32H39ClN2O5 |
| —— | 1-(2-(methylthio)-4-phenyl-4H-chromen-3-yl)ethanone | 1245449-11-9 | C18H16O2S |
| —— | 2,2,2-trichloroethyl N-[(1R,11R,14R,19R)-8-methyl-15-oxo-9-prop-2-enoxy-19-(trityloxymethyl)-4,6,16-trioxa-12-thia-18-azatetracyclo[9.6.2.02,10.03,7]nonadeca-2,7,9-trien-14-yl]carbamate | 654644-04-9 | C41H39Cl3N2O8S |
| —— | methyl (6-((2,6-dimethylpyridin-3-yl)methoxy)-4,7-dimethyl-2,3-dihydro-1-benzofuran-3-yl)acetate | 1452478-39-5 | C21H25NO4 |
| —— | {(3S)-6-[(1R)-6-methyl-4-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester | 1380388-62-4 | C22H21F3O4 |
| —— | 8-benzyl-1-phenyl-11-oxa-14-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-10,12,15-trione | 87748-23-0 | C26H19NO4 |
| —— | (+/-)-{[7-(2,4-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-83-5 | C17H17Cl2NO |
| —— | 6-Ethoxy-2,3,4,4a-tetrahydro-1H-dibenzofuran-9b-ethylamin | 93148-34-6 | C16H23NO2 |
| —— | 2-Hexyl-7-nitro-2,3-dihydro-benzofuran-5-ol | 161761-06-4 | C14H19NO4 |
| —— | 5-(but-2-ynyloxy)-2,3-dihydrobenzofuran | 1265905-61-0 | C12H12O2 |
| —— | 2-bromo-N-(2-methyl-2,3-dihydro-1-benzofuran-5-yl)hexanamide | 113746-81-9 | C15H20BrNO2 |
| —— | 3-(5-methyl-2,3-dihydro-benzofuran-7-yl)-propionyl chloride | 109016-26-4 | C12H13ClO2 |
| —— | 6-(2,6-dimethylphenyl)spiro[2,4-dihydrochromene-3,4'-5H-1,3-oxazole]-2'-amine | 1221161-62-1 | C19H20N2O2 |
| —— | (+/-)-{[7-(2-chlorophenyl)-5-phenyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852120-09-3 | C22H20ClNO |
| —— | (+/-)-2-(azidomethyl)-7-(2-chlorophenyl)-6-fluoro-2,3-dihydro-1-benzofuran | 852118-07-1 | C15H11ClFN3O |
| —— | 2-Ethoxycarbonyl-3.5-dimethylcumaran-3-essigsaeureethylester | 93737-79-2 | C17H22O5 |
| —— | 3-iodomethyl-3-methyl-2,3-dihydrobenzofuran-5-carboxylic acid methyl ester | 1266570-77-7 | C12H13IO3 |
| —— | N-Cyclopentyl-2,3-dihydro-3-phenyl-benzofuran-3-carboxamid | 94684-71-6 | C20H21NO2 |
| —— | (4E,4aS,9bR)-4-(diethylaminomethylidene)-8,9b-dimethyl-4aH-dibenzofuran-3-one | 86657-80-9 | C19H23NO2 |
| —— | methyl ((3S)-6-(1-(2,4-dichlorophenyl)ethoxy)-2,3-dihydro-1-benzofuran-3-yl)acetate | 1452477-80-3 | C19H18Cl2O4 |
| —— | 5-methyl-2,3-dihydro-benzofuran-7-carbaldehyde-(2,4-dinitro-phenylhydrazone) | 132982-06-0 | C16H14N4O5 |
| —— | 4,8-dimethoxy-2,2-dimethyl-chroman-3-ol | 13229-70-4 | C13H18O4 |
| —— | methyl 4-[(1R,2R,3aS,8bS)-2-acetyloxy-1-[(E,4R)-4-methyl-3-oxooct-1-en-6-ynyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoate | 274250-71-4 | C27H32O6 |
| —— | 9-(Aminomethyl)-3,3,4,4-tetrafluoro-2,5-dihydro-1,6-benzodioxocine-8-carbonitrile;hydrochloride | 1300042-65-2 | C12H10F4N2O2*ClH |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(4-methyl-1,2,5-oxadiazol-3-yl)-acetamide | 1048959-57-4 | C22H30N4O3 |
| —— | 2-(3-methyl-2-oxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-4-yl)-3-oxo-2-phenyl-butyronitrile | 23240-88-2 | C19H16N2O3 |
| —— | trans-2-Hydroymethyl-4-phenyl-4-chroman-carbonsaeure | 95280-50-5 | C17H16O4 |
| —— | (1'S,2'S,10'R,12'R,13'S)-2'-ethenyl-7'-methoxyspiro[1,3-dioxolane-2,11'-9-oxatetracyclo[10.2.1.02,10.03,8]pentadeca-3(8),4,6-triene]-13'-ol | 358753-71-6 | C19H22O5 |
| —— | (1'S,6'R)-2'-methyl-6'-(naphthalen-1-yl)-2H-spiro[benzofuran-3,1'-cyclohex[2]ene]-2,4'-dione | 1459161-11-5 | C24H18O3 |
| —— | 6-hydroxy-7-isobutyl-(2H)3-phenyl-benzofuran | 194855-61-3 | C18H20O2 |
| —— | 5-acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran | 190841-53-3 | C20H30O4 |
| —— | (S)-6,7-dichloro-2-(phenylthiomethyl)-2,3-dihydrobenzofuran | 118206-08-9 | C15H12Cl2OS |
| —— | 6-(but-2-ynyloxy)-5-propyl-2,3-dihydrobenzofuran | 1265905-62-1 | C15H18O2 |