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-fluoro-5-[1-(2-methylpropylsulfonyl)-3,6-dihydro-2H-pyridin-4-yl]-2,3-dihydro-1-benzofuran-2-yl]piperidin-1-yl]-5-propylpyrimidine | 1346529-37-0 | C29H39FN4O3S |
| —— | 3-(2-Hydroxymethyl-4,5-dimethoxy-benzyl)-6-methoxy-2,3-dihydro-benzofuran-3-ol | 99877-77-7 | C19H22O6 |
| —— | 3aα-<2'-Carboxy-ethyl>-3α-carboxymethyl-1.3.3a.8b-tetrahydro-8bα-hydroxy-1.3β.6.8-tetramethyl-2.4-dioxacyclopenta-<a>-inden | 111476-17-6 | C19H24O7 |
| —— | N-propyl (7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)thioamide | 178322-36-6 | C18H27NOS |
| —— | 2-(Methoxycarbonyl)-3-cyclohexyl-2,3-dihydrobenzo<b>furan | 344763-74-2 | C16H20O3 |
| —— | 2,3-Dimethoxy-3-methyl-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester | 63500-11-8 | C14H18O5 |
| —— | (2S,4R)-7-chloro-2-(fluoromethyl)-2-methylchroman-4-amine | 1443652-64-9 | C11H13ClFNO |
| —— | 2-[4-[2-methyl-5-[1-(2-methylpropylsulfonyl)-3,6-dihydro-2H-pyridin-4-yl]-3H-1-benzofuran-2-yl]piperidin-1-yl]-5-propylpyrimidine | 1346529-25-6 | C30H42N4O3S |
| —— | (3aR,8bR)-1,3a,6,8b-tetramethyl-3H-cyclopenta[b][1]benzofuran | 138629-62-6 | C15H18O |
| —— | Bis-<cumaran-(5)-yl>-trisulfid | 94501-14-1 | C16H14O2S3 |
| —— | 98941-41-4 | C21H28O5 | |
| —— | (S)-1-(2,3-Dihydrobenzofuran-5-yl)ethanamine | 1241683-77-1 | C10H13NO |
| —— | 157232-80-9 | C16H18O4 | |
| —— | 2-Methyl-2,3-dihydro-1-benzofuran-3-amine hydrochloride | 1803594-11-7 | C9H12ClNO |
| —— | (+/-)-{[7-(3-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-77-7 | C17H18ClNO |
| —— | (+/-)-N-methyl-1-(7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methanamine | 852124-35-7 | C15H16N2O |
| —— | 4-[(1R,3R)-3-(2,3-dihydro-1-benzofuran-4-yl)-2,2-dimethylcyclopropyl]-1,3-thiazol-2-amine | 335061-25-1 | C16H18N2OS |
| —— | 1196967-60-8 | C22H37N3O3S | |
| —— | 2-(2,3-Cyclohexylenedioxy-5-formyl-4-isopropylphenyl)-1,3-dioxane | 213682-27-0 | C20H26O5 |
| —— | [5-Methoxy-benzofuran-(3Z)-ylidene]-acetonitrile | 39581-42-5 | C11H9NO2 |
| —— | 6-Methoxy-2,3-epoxy-2-methyl-3-(4-methoxyphenyl)-cumaron | 104645-15-0 | C17H16O4 |
| —— | (4a<i>RS</i>,11a<i>RS</i>)-6a-methoxy-4a,6<i>c</i>,7,9-tetramethyl-3-oxo-(4a<i>r</i>,6a<i>t</i>)-2,3,4,4a,6,6a-hexahydro-1<i>H</i>-benzofuro[3a,3-<i>b</i>]benzofuran-4-carboxylic acid ethyl ester | 101632-31-9 | C22H28O6 |
| —— | pyrimidine-4,6-dicarboxylic acid 4-[(4-chloro-thiophen-2-ylmethyl)-amide] 6-[(2,3-dihydro-benzofuran-5-ylmethyl)-amide] | 691002-79-6 | C20H17ClN4O3S |
| —— | (rac)-3-azido-6-bromo-2,3-dihydrobenzofuran | 1392072-56-8 | C8H6BrN3O |
| —— | 5,10β-Isoproylidendioxy-4β-acetoxy-9-oxo-1,2,3,4,4ah,9,9ah,10-octahydro-anthracen | 100024-75-7 | C19H22O5 |
| —— | 6-[(6,7-epoxy-3,7-dimethylnonyl)-oxy]-2,3-dihydrobenzofuran | 51079-64-2 | C19H28O3 |
| —— | dimethyl 2-[(5-fluoro-2,3-dihydrobenzofuran-3-yl)methyl]malonate | 147373-13-5 | C14H15FO5 |
| —— | (+/-)-{[7-(4-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-79-9 | C17H18ClNO |
| —— | (2,4-dinitro-phenylhydrazono)-(5-methyl-2,3-dihydro-benzofuran-7-yl)-acetic acid ethyl ester | 102017-84-5 | C19H18N4O7 |
| —— | (1aS,7bR)-2,2,7b-Trimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene | 137838-04-1 | C12H14O2 |
| —— | 2-(4-chloro-phenyl)-4,4-diethyl-4H-benzo[e][1,3]oxazine | 27507-92-2 | C18H18ClNO |
| —— | 2-[(1R,2R,6S,7R,9R)-7-hydroxy-12-methoxy-4,4-dimethyl-3,5,10-trioxatetracyclo[7.7.0.02,6.011,16]hexadeca-11(16),12,14-trien-1-yl]-N,N-dimethylacetamide | 1256603-63-0 | C20H27NO6 |
| —— | 1-((R)-6-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl)-4-(methoxymethoxy)but-2-yn-1-ol | 1058196-67-0 | C25H38O7Si |
| —— | 2-[5-(2,3-dihydro-1-benzofuran-7-ylmethoxy)pyrazol-1-yl]pyridine-4-carbonitrile | 1613413-16-3 | C18H14N4O2 |
| —— | [4-Chloro-1-(1-methylethyl)-1H-pyrazol-5-yl](2,3-dihydro-5-benzofuranyl)methanone | 1779328-32-3 | C15H15ClN2O2 |
| —— | 6,7-Dihydrobenzo[d][1]benzoxepine-4,10-dicarbonyl chloride | 1414957-43-9 | C16H10Cl2O3 |
| —— | 4β,9β-Dihydroxy-5,10β-benzylidendioxy-1,4,4aα,9,9aα,10-hexahydro-anthracen | 107744-73-0 | C21H20O4 |
| —— | 2,2,3,3,5-pentamethyl-2,3-dihydro-benzofuran | 57858-97-6 | C13H18O |
| —— | 5-chloro-2-[4-[7-fluoro-5-[1-(2-methylpropylsulfonyl)-3,6-dihydro-2H-pyridin-4-yl]-2,3-dihydro-1-benzofuran-2-yl]piperidin-1-yl]pyrimidine | 1346529-42-7 | C26H32ClFN4O3S |
| —— | Mononguanylhydrazon der Usninsaeure | 18719-23-8 | C19H20N4O6 |
| —— | (2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)methanamine | 132570-56-0 | C11H15NO |
| —— | trans-4-[([1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,4-dioxo-thiazolidin-3-yl)-ethoxy]-3-methyl-benzyl}-amino)-methyl]-cyclohexanecarboxylic acid | 1443020-04-9 | C31H38N2O6S |
| —— | 2-methoxy-2,5-dimethyl-2,3-dihydro-benzofuran-3-ol | 63514-76-1 | C11H14O3 |
| —— | (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-N-(2,3,5,6-tetramethylbenzyl)-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925439-65-2 | C28H29NO7 |
| —— | 1174720-62-7 | C25H29NO3 | |
| —— | 7-tert-butyl-2,4-dimethyl-2,3-dihydrobenzofuran | 1033621-21-4 | C14H20O |
| —— | 1319730-56-7 | C18H16O2 | |
| —— | (R)-3-(4-phenylbutyl)‑2,3-dihydrobenzofuran | 1571984-97-8 | C18H20O |
| —— | 2-(5-amino-1H-tetrazol-1-yl)-N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)methyl]piperidin-4-yl}methyl)-acetamide | 1048960-42-4 | C20H29N7O2 |
| —— | 1-((2R,3S)-2,3-dihydro-6-methyl-3-(nitromethyl)benzofuran-2-yl)ethanone | 1384976-62-8 | C12H13NO4 |