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 |
|---|---|---|---|
| —— | 3-(2,3-dihydro-benzofuran-2-yl)-propionic acid amide | 857551-61-2 | C11H13NO2 |
| —— | tert-butyl 9-[(1E)-3-methoxypropa-1-ene-1-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate | 1055880-86-8 | C18H25NO4 |
| —— | 1-((2R,3S)-2,3-dihydro-7-methoxy-3-(nitromethyl)benzofuran-2-yl)ethanone | 1384976-54-8 | C12H13NO5 |
| —— | Aflatoxin RB1 | 56217-83-5 | C17H18O6 |
| —— | 1,2'-anhydro-2,6-dideoxy-5-C-(2-hydroxy-5-methylphenyl)-α-DL-erythro-hex-3-ulose | 112576-18-8 | C13H14O4 |
| —— | 3,3-dimethyl-5-[(1S,2S)-1,2-methano-1-methyl-3-oxo-propyl]-7-phenyl-2,3-dihydro-benzofuran | 623176-49-8 | C21H22O2 |
| —— | 6-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanylmethyl)-8-methyl-4H-1,3-benzoxathiine | 1192176-27-4 | C20H15F17OS2 |
| —— | 2-(acetoxymethyl)-7-chloro-2,3-dihydro-5-nitro-6-(β-nitrovinyl)benzofuran | 88062-19-5 | C13H11ClN2O7 |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-(3,5-dimethylphenyl)amine | 852115-30-1 | C17H20N2O |
| —— | 2-(7-(tert-butyl)-3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1403387-65-4 | C20H31BO3 |
| —— | ethyl-7,8-diamino-chroman-2-carboxylate | 440635-73-4 | C12H16N2O3 |
| —— | 6-[2-(2-amino-1H-imidazol-5-yl)ethylamino]-3-[(3,4-dichlorophenyl)methyl]-1-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1,3,5-triazine-2,4-dione | 1148128-08-8 | C24H23Cl2N7O3 |
| —— | 6,7-Dichloro-5-(2-methylsulfanyl-1H-pyrrole-3-carbonyl)-2,3-dihydro-benzofuran-2-carboxylic acid tert-butyl ester | 126201-12-5 | C19H19Cl2NO4S |
| —— | [2-(4,6-Dimethoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-5-carbonyl)-3,5-dimethoxy-phenyl]-acetonitrile | 35036-19-2 | C23H23NO7 |
| —— | 2-(2-methyl-2,3-dihydrobenzofuran-2-yl)acetonitrile | 1372769-11-3 | C11H11NO |
| —— | (2R,3S)-4-hydroxy-2,3-dimethyl-2,3-dihydro-benzofuran-3-carbonitrile | 474418-74-1 | C11H11NO2 |
| —— | 6,7-Dichloro-5-{2-[5-methyl-thiazolidin-(2E)-ylidene]-acetyl}-2,3-dihydro-benzofuran-2-carboxylic acid | 126200-75-7 | C15H13Cl2NO4S |
| —— | (R)-1-[(S)-5-tert-butyl-2,3-dihydrobenzofuran-2-yl]ethanol | 1269598-93-7 | C14H20O2 |
| —— | 5-Chloro-3-pyridin-3-yl-7,8-dihydrofuro[2,3-g][1,2]benzoxazole-7-carboxylic acid | 136741-35-0 | C15H9ClN2O4 |
| —— | (3-hydroxy-3-methylspiro[1-benzofuran-2,2'-oxane]-3'-yl) acetate | 130467-17-3 | C15H18O5 |
| —— | 3-(dimethylamino)-2,2(3H)-benzofurandicarboxylic acid 2,2-diethyl ester | 1447798-28-8 | C16H21NO5 |
| —— | (+/-)-{[5-fluoro-7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-38-0 | C16H15ClFNO |
| —— | 3,3-dimethyl-5-[(1S,2S)-3-hydroxy-1,2-methano-1-methyl-propyl]-7-phenyl-2,3-dihydro-benzofuran | 623176-48-7 | C21H24O2 |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid {3-[3-(4-fluoro-3-methyl-phenyl)-pyrazine-2-carbonyl]-thiazolidin-2-ylmethyl}-amide | 1204585-56-7 | C25H23FN4O3S |
| —— | 15,16-dinor-4α-acetoxy-8-methoxy-12,13-epoxy-6,8,10-trichothecatriene | 72229-66-4 | C16H18O5 |
| —— | 9b-methyl-1,2,4a,9b-tetrahydrodibenzo[b,d]furan | 1450980-99-0 | C13H14O |
| —— | 1-(3-acetylspiro[4H-chromene-2,1'-cyclopentane]-3-yl)ethanone | 1173178-87-4 | C17H20O3 |
| —— | 2-((2R,3R)-5-Chloro-2-hydroxymethyl-2,3-dihydro-benzofuran-3-yl)-ethanol | 70554-71-1 | C11H13ClO3 |
| —— | 3-Oxo-6-morpholino-1-oxa-julolidin | 23866-24-2 | C15H18N2O3 |
| —— | 2-Phenyl-2a,7a-dihydro-7-oxa-cyclobuta[a]indene | 65933-77-9 | C16H12O |
| —— | 5-(4-methanesulfonylmethyl-phenyl)-2-[1-(5-propyl-[1,2,4]oxadiazol-3-yl)-piperidin-4-yl]-2,3-dihydro-furo[2,3-c]pyridine | 1391081-37-0 | C25H30N4O4S |
| —— | 2-(4-amino-1,2,5-oxadiazol-3-yl)-N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-acetamide | 1048959-24-5 | C21H29N5O3 |
| —— | 2-(2'-hydroxyethoxy)-2,3-dihydro-3-methylenebenzofuran | 1187956-28-0 | C11H12O3 |
| —— | 6,7-Dichloro-5-[(E)-3-(2-fluoro-phenylamino)-3-methylsulfanyl-acryloyl]-2,3-dihydro-benzofuran-2-carboxylic acid | 126200-68-8 | C19H14Cl2FNO4S |
| —— | 3-(4-vinyl-benzyl)-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester | 936563-60-9 | C19H18O3 |
| —— | 6-Methyl-3-methylene-4-phenyl-chroman-2-one | 98061-75-7 | C17H14O2 |
| —— | 1,2'-anhydro-2,6-dideoxy-5-C-(2-hydroxy-5-methylphenyl)-α-DL-erythro-hex-3-ulose 5-acetate | 112576-19-9 | C15H16O5 |
| —— | di-Boc-(R)-4-(5-bromo-2-fluorophenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-1,3-oxazin-2-amine | 1414877-57-8 | C21H26BrF3N2O5 |
| —— | (2R,3R)-5-Chloro-3-methoxycarbonylmethyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 70554-67-5 | C13H13ClO5 |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid {3-[2-(ethyl-methyl-amino)-5-(4-fluoro-phenyl)-thiazole-4-carbonyl]-thiazolidin-2-ylmethyl}-amide | 1204585-48-7 | C26H27FN4O3S2 |
| —— | methyl 2-((S)-6-(N-((S)-7-(2,5-dimethylthiophen-3-yl)-2,3-dihydrobenzofuran-3-yl)-2,2,2-trifluoroacetamido)-2,3-dihydrobenzofuran-3-yl)acetate | 1258401-86-3 | C27H24F3NO5S |
| —— | benzofuran-2,3-dione 2-[O-(2-bromoethyl)-oxime] 3-(O-methyloxime) | 249298-67-7 | C11H11BrN2O3 |
| —— | (3R)-3-(3,4-dimethylphenyl)-3,5,6-trimethyl-1-benzofuran-2-one | 1418028-14-4 | C19H20O2 |
| —— | (+/-)-N-[2-(aminomethyl)-2,3-dihydro-1-benzofuran-7-yl]-N-(4-methylphenyl)amine | 852114-90-0 | C16H18N2O |
| —— | 5-(2-fluoro-4-methanesulfonylmethyl-phenyl)-2-[1-(5-propyl-[1,2,4]oxadiazol-3-yl)-piperidin-4-yl]-2,3-dihydro-furo[2,3-c]pyridine | 1391081-49-4 | C25H29FN4O4S |
| —— | 5a,6,7,8,9,9a-Hexahydro-5a(4-methyl-1-piperazinyl)-dibenzofuran-2-ol | 5117-27-1 | C17H24N2O2 |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid [3-(2-m-tolyl-thiophene-3-carbonyl)-thiazolidin-2-ylmethyl]-amide | 1204584-53-1 | C25H24N2O3S2 |
| —— | [(5-methyl-4<i>H</i>-benzo[1,3]dioxin-6-ylamino)-methylene]-malonic acid diethyl ester | 36038-06-9 | C17H21NO6 |
| —— | 10-Hydroxy-1,5,9-trimethyl-8-oxa-tricyclo[7.2.1.02,7]dodeca-2,4,6-trien-12-one | 74552-40-2 | C14H16O3 |
| —— | (R,E)-ethyl 3-(2,3-dihydrobenzofuran-2-yl)acrylate | 1177405-65-0 | C13H14O3 |