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 |
|---|---|---|---|
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-pyrazin-2-ylacetamide | 1048959-76-7 | C23H30N4O2 |
| —— | 4-fluoro-2,3-dihydro-1-benzofuran-3-amine hydrochloride | 1384265-54-6 | C8H8FNO*(x)ClH |
| —— | 6-(1-benzofuran-5-yl)-5-phenyl-1,2,4-triazin-3-amine | 1321513-12-5 | C17H12N4O |
| —— | tert-butyl 4-[(E)-(6-nitro-2,3-dihydrochromen-4-ylidene)methyl]imidazole-1-carboxylate | 1049633-98-8 | C18H19N3O5 |
| —— | pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydro-benzofuran-5-ylmethyl)-amide] 6-[(2,5-dimethyl-furan-3-ylmethyl)-amide] | 691002-00-3 | C22H22N4O4 |
| —— | 6,7-Dichloro-2,3-dihydro-1-benzofuran-3-amine hydrochloride | 1258639-72-3 | C8H8Cl3NO |
| —— | 2-tert-butyl-1,3-dioxa-4,5-benzocycloheptene | 93953-88-9 | C13H18O2 |
| —— | N-(1-{4-[(hydroxyamino)carbonyl]phenyl}ethyl)-2,3-dihydro-1-benzofuran-7-carboxamide | 1332890-62-6 | C18H18N2O4 |
| —— | 3-iodo-8-tert-butyl-4-phenylselenyl-2H-benzopyran | 1147711-24-7 | C19H19IOSe |
| —— | 2,3-Dihydro-benzofuran-2-carboxylic acid [4-(4-isopropoxy-phenyl)-thiazol-2-yl]-amide | 15850-64-3 | C21H20N2O3S |
| —— | acetoxy-6 hydroxy-11 dihydro-6,11 dibenzo<b,e>oxepinne | 344447-57-0 | C16H14O4 |
| —— | 2,3-Dihydro-2,2,4,7-tetramethyl-5-benzofuranol | 26172-17-8 | C12H16O2 |
| —— | (S)-2-(3-((tert-butoxycarbonyl)((R)-1-(4-fluoronaphthalen-1-yl)ethyl)amino)propyl)-2H-chromen-4-yl trifluoromethanesulfonate | 1451374-13-2 | C30H31F4NO6S |
| —— | 2,2,3,3-tetrafluoro-2,3-dihydrobenzofuran-7-yl chloride | 114851-25-1 | C8H3ClF4O |
| —— | 2-[3-(4-Chlorophenyl)-2,3-dihydro-2-oxo-3-benzofuranyl]acetic acid | 118709-25-4 | C16H11ClO4 |
| —— | 2-azidomethyl-4-phenyl-6-fluoro-benzo[1,3]dioxole | 913630-23-6 | C14H10FN3O2 |
| —— | 6-methyl-5-propionyl-2,3-dihydro-benzofuran-2-carboxylic acid | 26018-50-8 | C13H14O4 |
| —— | Acetic acid 6,7-dichloro-4-dimethylsulfamoyl-2,3-dihydro-benzofuran-2-ylmethyl ester | 113730-27-1 | C13H15Cl2NO5S |
| —— | 92514-00-6 | C21H20FNO6 | |
| —— | 6-cyano-3,3-ethylenedioxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran | 134255-91-7 | C14H15NO3 |
| —— | 1,5,9-Trimethyl-8-oxa-tricyclo[7.2.1.0<sup>2,7</sup>]dodeca-2,4,6-trien-12-one | 178171-62-5 | C14H16O2 |
| —— | 3,4-Dibromo-5-chloro-2,2-dimethyl-chroman | 80055-57-8 | C11H11Br2ClO |
| —— | 2-Imino-5-(6-phenylmethoxy-2,3-dihydro-1-benzofuran-3-yl)-1,3-thiazolidin-4-one | 905724-87-0 | C18H16N2O3S |
| —— | (1S,2R)-2-aminomethyl-1-(2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid allyl-prop-2-ynyl-amide | 947766-54-3 | C19H22N2O2 |
| —— | 2-Butylaminomethyl-5-chlor-8-hydroxy-benzodioxan | 101263-78-9 | C13H18ClNO3 |
| —— | [4-amino-2-[4-(2-ethylamino-ethoxy)-phenylamino]-thiazol-5-yl]-(2,3-dihydro-benzofuran-5-yl)-methanone | 627462-96-8 | C22H24N4O3S |
| —— | 2,2,3,5-Tetramethylcumaron | 100256-13-1 | C12H16O |
| —— | 2,2,4,6,7-pentamethyl-N-((2-(phenylthio)ethyl)carbamothioyl)-2,3-dihydrobenzofuran-5-sulfonamide | 1442564-41-1 | C22H28N2O3S3 |
| —— | 7-Methyl-2-(3-isopropyloxypropylaminomethyl)-2,3-dihydro-benzofuran | 17793-76-9 | C16H25NO2 |
| —— | 7-methyl-2,3,4,4a,5,6,7,7a,8,13a-decahydro-1H-<1>-benzopyrano<2,3-j>isoquinoline hydrobromide | 40135-80-6 | BrH*C17H23NO |
| —— | 6-(trifluoromethyl)-2,3-dihydrobenzofuran | 1391072-82-4 | C9H7F3O |
| —— | (1S,2R)-2-aminomethyl-1-(2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid di-prop-2-ynyl-amide | 947766-47-4 | C19H20N2O2 |
| —— | N-(2-chloropyrimidin-4-yl)-N-isobutyl-2,3-dihydrobenzofuran-5-carboxamide | 1224600-19-4 | C17H18ClN3O2 |
| —— | 2,6-dimethyl-5-nitro-2,3-dihydrobenzo<2,3>furan | 140427-41-4 | C10H11NO3 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(3,5-dimethylisoxazol-4-yl)-acetamide | 1048959-58-5 | C24H33N3O3 |
| —— | (R,S)-5-iodo-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 847949-06-8 | C10H9IO3 |
| —— | (9aS)-8-acetyl-N-(furan-2-ylmethyl)-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxodibenzofuran-4-carboxamide | 1227077-79-3 | C22H19NO8 |
| —— | 1-(6-hydroxy-2,3-dihydro-benzofuran-5-yl)-but-2<i>t</i>-en-1-one | 107058-03-7 | C12H12O3 |
| —— | N'-tert-butyl-2,3-dihydro-2-methylbenzofuran-6-carbohydrazide | 1261963-70-5 | C14H20N2O2 |
| —— | Oxalic acid methyl ester (6aS,11bR)-3,9,10-tris-benzyloxy-7,11b-dihydro-indeno[2,1-c]chromen-6a-yl ester | 176222-28-9 | C40H34O8 |
| —— | 2-Ethyl-5-hydroxy-2,3-dihydro-benzofuran | 3780-52-7 | C10H12O2 |
| —— | (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-N-[2,3,6-trimethyl-4-(2-pentynyloxy)benzyl]-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925440-32-0 | C32H33NO8 |
| —— | 1-cyano-2,3-dihydro-2-phenylspiro<benzofuran-3,4'-piperidine> | 79242-49-2 | C19H18N2O |
| —— | (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-N-(thiophen-3-ylmethyl)dibenzofuran-4-carboxamide | 1227077-82-8 | C22H19NO7S |
| —— | 2-(2,3-dihydrobenzofuran-7-yl)hydrazinesulfonic acid, potassium salt | 80959-13-3 | C8H9N2O4S*K |
| —— | 2,3-Dihydro-benzofuran-2-carboxylic acid [4-(4-butoxy-phenyl)-thiazol-2-yl]-amide | 15850-71-2 | C22H22N2O3S |
| —— | 2-(2-p-chlorophenylethyl)-6-[3-hydroxy-propyl]5-tertbutyldimethylsilyloxy-2,3-dihydrobenzofuran | 138854-15-6 | C25H35ClO3Si |
| —— | 3-(2,3-dihydrobenzofuran-5-yl)-7-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2,6-dimethylpyrazolo[5,1-b]oxazole | 1207258-99-8 | C19H19N5O2 |
| —— | 5-chloro-3-methoxycarbonylaminobenzo[b]furan-2(3H)-one | 203519-78-2 | C10H8ClNO4 |
| —— | 6,7-dichloro-5-(4-oxothiazolidin-2-ylidene)acetyl-2,3-dihydro-2-benzo<b>furancarboxylic acid | 105978-80-1 | C15H11Cl2NO5S |