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 |
|---|---|---|---|
| —— | (+/-)-5-acetyloxy-2,3-dihydro-4,6,7-trimethyl-2-benzofuranacetyl chloride | 128232-49-5 | C15H17ClO4 |
| —— | 3-(4-fluorophenyl)benzofuran-2(3H)-one | 1314114-25-4 | C14H9FO2 |
| —— | 4-(2-(1-(propylsulfonyl)piperidin-4-yl)-2,3-dihydrobenzofuran-5-yl)-1,2,3,6-tetrahydropyridine | 1346529-84-7 | C21H30N2O3S |
| —— | S-3-<2,3-Dihydro-6,7-dimethoxy-2-(1-hydroxy-1-methylethyl)-5-benzofuranyl>-1-propanol | 78796-64-2 | C16H24O5 |
| —— | 2'(RS),3(RS)-succinyloxy-3,4-dihydro-8-<3'-(N-acetyl-N-isopropyl)amino>propoxy-2H-1-benzopyran | 100922-09-6 | C21H27NO7 |
| —— | N-(((2S)-1-Ethyl-2-pyrrolidinyl)methyl)-2,3-dihydro-5-(iodo-123I)-7-benzofurancarboxamide | 129693-77-2 | C16H21IN2O2 |
| —— | 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-2-propionyl-3-hydroxycyclohex-2-en-1-one | 157189-19-0 | C22H28O4 |
| —— | (E)-ethyl 3-(5-(1-(S)-((tert-butylsulfinyl)imino)ethyl)-2,3-dihydrobenzofuran-4-yl) acrylate | 1448715-66-9 | C19H25NO4S |
| —— | [7-(3-methoxypropoxy)-1-Dihydrobenzofuran-5-yl]methanol | 1093083-47-6 | C13H18O4 |
| —— | 4-(5-bromo-2,3-dihydrobenzofuran-2-yl)-1-(propylsulfonyl)piperidine | 1346529-75-6 | C16H22BrNO3S |
| —— | 1-(5-methyl-2,3-dihydro-benzofuran-7-yl)-ethanone oxime | 121159-64-6 | C11H13NO2 |
| —— | 3-ethyl 4-methyl 2-chloro-7-fluoro-5-hydroxy-2-(trifluoromethyl)-2,3-dihydrobenzo[b]oxepine-3,4-dicarboxylate | 1354633-01-4 | C16H13ClF4O6 |
| —— | 6-methoxy-2,2-dimethyl-3-phenyl-2,3-dihydro-benzofuran-3-ol | 28856-53-3 | C17H18O3 |
| —— | 2,8-bis(allyloxy)-3,7-diiodo-2,8-dimethyl-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene | 1147120-57-7 | C20H24I2O4 |
| —— | (4(R)-azido-6-chloro-chroman-7-ylmethyl)-tert-butylamine | 828925-94-6 | C14H19ClN4O |
| —— | (R)-4-(t-butyldimethylsilyloxy)-2-isopropenyl-6-hydroxy-2,3-dihydrobenzofuran-5-carbaldehyde | 1058196-62-5 | C18H26O4Si |
| —— | 4-(1-(2-methoxyphenyl)vinyl)-5-methyl-2,3-dihydrobenzofuran | 1582778-63-9 | C18H18O2 |
| —— | N-Acetyl-3-ethylamino-7-methyl-cumaran | 92040-49-8 | C13H17NO2 |
| —— | (S)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid | 130981-36-1 | C10H11NO5S |
| —— | 4-(6-bromo-4H-1,3-benzodioxin-2-yl)piperidine | 1200575-54-7 | C13H16BrNO2 |
| —— | 2-t-butoxy-2,3-dihydro-3-methylenebenzofuran | 1187956-13-3 | C13H16O2 |
| —— | (S)-2-amino-6-(5-(2,3-dihydrobenzofuran-7-ylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one | 1357098-03-3 | C22H25FN4O2 |
| —— | 8-Methyl-2,3,3a,9b-tetrahydro-thieno[3,2-c]chromen-4-one | 79043-34-8 | C12H12O2S |
| —— | 2-Methoxy-chroman-carbonsaeure-(3)-methylester | 105254-36-2 | C12H14O4 |
| —— | 5-[(5-bromo-2-chloro-phenyl)methyl]-2,3-dihydrobenzofuran | 1358580-56-9 | C15H12BrClO |
| —— | N-[5-[4-[5-(2,3-dihydro-1-benzofuran-2-carbonylamino)-1,3,4-thiadiazol-2-yl]butyl]-1,3,4-thiadiazol-2-yl]-2,3-dihydro-1-benzofuran-2-carboxamide | 1439389-84-0 | C26H24N6O4S2 |
| —— | 3-Brom-4-<2-hydroxy-phenyl>-chroman | 29415-78-9 | C15H13BrO2 |
| —— | 2-(4-(5-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)-5-(trifluoromethyl)pyrimidine | 1602575-17-6 | C23H25F3N4O |
| —— | 5-chloro-2-(4-(5-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)pyrimidine | 1602575-15-4 | C22H25ClN4O |
| —— | 3',4',5',6'-tetrahydroxy-3-methyl-spiro[furan-2,9'-xanthen]-5-one | 99387-44-7 | C17H12O7 |
| —— | 2,2-dimethyl-3H-1-benzofuran-7-diazonium;sulfate | 68298-47-5 | C10H11N2O5S- |
| —— | 8a-methyl-3a,8a-dihydro-3H-furo[2,3-b]benzofuran-2-one | 99846-05-6 | C11H10O3 |
| —— | (2R)-1-(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)propan-2-amine | 2227988-71-6 | C12H17NO |
| —— | (1S,2S,3aS,8bS)-1-bromo-5-[4-(oxan-2-yloxy)butyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-ol | 79020-62-5 | C20H27BrO4 |
| —— | 4-[[2,3-dihydro-5-(phenylmethyl)benzo[b]furan-2-yl]methyl]-4H-imidazo[4,5-b]pyridine, hydrochloride | 179399-05-4 | C22H19N3O*ClH |
| —— | (1S,3R)-3-[([(R)-1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclopentanecarboxylic acid | 1443020-84-5 | C31H38N2O7 |
| —— | (5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanol | 1282733-55-4 | C15H12BrClO2 |
| —— | 2-(2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)acetic acid | 57898-96-1 | C12H14O3 |
| —— | 267222-98-0 | C37H62O5Si2 | |
| —— | 2,3-dihydro-benzofuran-4-carboxylic acid [(1S,3S,5S)-(2-azabicyclo[3.3.0]octane-3-yl)methyl]-amide | 1112139-29-3 | C17H22N2O2 |
| —— | 2,3-Dihydro-benzofuran-2-carboxylic acid (2-dimethylamino-ethyl)-pyridin-2-yl-amide | 47300-47-0 | C18H21N3O2 |
| —— | 5-Chlor-7-brom-2-methyl-cumaran | 90725-38-5 | C9H8BrClO |
| —— | 3-Dimethylaminomethyl-4-p-tolyl-chroman-4-ol | 94914-35-9 | C19H23NO2 |
| —— | 3-iodomethyl-7-methoxy-3-methyl-2,3-dihydrobenzofuran-5-carbaldehyde | 1266570-78-8 | C12H13IO3 |
| —— | (R)-2-(1,1-dimethyl-2-p-tolylethyl)-2,3-dihydrobenzofuran | 843667-56-1 | C19H22O |
| —— | (2,3-Dihydro-benzofuran-5-yl)-(4-fluoro-phenyl)-methanol | 87921-90-2 | C15H13FO2 |
| —— | N-(2-(3-Benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridinyl)ethyl)-2,3-dihydro-5-hydroxy-4,6,7-trimethylbenzofuran-2-acetamide | 272770-31-7 | C28H32N2O5 |
| —— | (2S,4S)-3,4-Dihydro-4-hydroxy-2-(1E)-1-propen-1-yl-2H-1-benzopyran-6-carboxylic acid | 2489622-58-2 | C13H14O4 |
| —— | 5-Methoxy-2-(3-isopropyloxypropylaminomethyl)-2,3-dihydrobenofuran | 21130-30-3 | C16H25NO3 |
| —— | 5-Chlor-2,3-dibrom-2,3-dihydrobenzofuran | 36826-29-6 | C8H5Br2ClO |