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 |
|---|---|---|---|
| —— | (Z)-N-((3-benzylidene-1,3-dihydroisobenzofuran-1-yl)(phenyl)methyl)aniline | 1448450-38-1 | C28H23NO |
| —— | 3-[2-(1-Hydroxy-1-methyl-ethyl)-4-methoxy-2,3-dihydro-benzofuran-7-yl]-N,N-dimethyl-propionamide | 40758-95-0 | C17H25NO4 |
| —— | 5,6,7,8-Tetrachloro-2-cyano-3-(5,6,7,8-tetrachloro-3a,9a-dihydro-benzo[b]furo[2,3-e][1,4]dioxin-2-yl)-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid ethyl ester | 31700-92-2 | C22H9Cl8NO7 |
| —— | 4-(2-(4-(trifluoromethyl)phenyl)-2,3-dihydrobenzofuran-2-yl)piperidine | 1304776-69-9 | C20H20F3NO |
| —— | 5-Benzofuranmethanol, I+/--(1-amino-1-methylethyl)-4-fluoro-2,3-dihydro- | 2090758-50-0 | C12H16FNO2 |
| —— | 4-[2-(4-trifluoromethyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine | 856936-16-8 | C19H18F3NO2 |
| —— | 2-Butyl-2-aethyl-6-methylcumaran | 25594-08-5 | C15H22O |
| —— | 6-Chlor-2,3-dibrom-2,3-dihydrobenzofuran | 36739-96-5 | C8H5Br2ClO |
| —— | 9-(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide | 1358753-41-9 | C17H18N2O3S |
| —— | 3-[3-(1-Hydroxy-1-methyl-ethyl)-6-methoxy-2,3,7,8-tetrahydro-furo[2',3':3,4]benzo[1,2-b][1,4]dioxin-5-yl]-N,N-dimethyl-propionamide | 30510-39-5 | C19H27NO6 |
| —— | 2-(2-chloro-5-(2,2-dicyanovinyl)-3-hydroxy-7,8-dihydro-6H-xanthen-9-yl)benzoic acid | 1448310-43-7 | C24H15ClN2O4 |
| —— | 4-(1-Diethylamino-4-pentylamino)-2,3-dihydro-2,2-dimethyl-benzofuran | 31010-96-5 | C19H32N2O |
| —— | 1',8'-dihydroxy-4',5'-bis-phenylazo-spiro[phthalan-1,9'-xanthen]-3-one | 857788-63-7 | C32H20N4O5 |
| —— | [(7-methoxy-2,3-dihydro-benzofuran-5-ylamino)-methylene]-malonic acid diethyl ester | 39487-39-3 | C17H21NO6 |
| —— | 15168-04-4 | C21H30O2 | |
| —— | 4-Benzyl-5,7-di-tert.butyl-1,4-dihydronaphthalin-1,4-endoxid | 37754-65-7 | C25H30O |
| —— | methyl 3-(2,3-dihydro-7-methoxybenzo<b>furan-3-yl)propionate | 155792-31-7 | C13H16O4 |
| —— | 39477-81-1 | C15H12O2 | |
| —— | Acetic acid (2R,3R,4R)-3-acetoxy-2-acetoxymethyl-7-methoxy-chroman-4-yl ester | 637331-52-3 | C17H20O8 |
| —— | 4,5-Benzo-7-cyclopropylimino-3,8-dioxa-6-phenyl-bicyclo<4.2.1>nonan | 10527-43-2 | C20H19NO2 |
| —— | 5-(1-Amino-4-pentylamino)-2,3-dihydro-2,2-dimethyl-benzofuran-fumarat | 30311-67-2 | C4H4O4*C15H24N2O |
| —— | 1044218-03-2 | C30H28O4 | |
| —— | 7-(1-Diethylamino-4-pentylamino)-2,3-dihydro-2,2-dimethyl-benzofuran | 31010-99-8 | C19H32N2O |
| —— | 4-(p-Anisyl)-2-hydroxy-3-methyl-chroman | 18992-97-7 | C17H18O3 |
| —— | 5-(1-Diethylamino-4-pentylamino)-2,3-dihydro-2,2-dimethyl-benzofuran | 31010-97-6 | C19H32N2O |
| —— | [(3S)-6-({7-[1-(difluoromethyl)-3,5-dimethyl-1H-pyrazol-4-yl]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-50-7 | C24H23F2N3O4 |
| —— | (6S,7R)-9-Hydroxy-8-hydroxymethyl-6-phenyl-2,3,6,7,8,9-hexahydro-naphtho[2,3-b][1,4]dioxine-7-carboxylic acid | 126382-42-1 | C20H20O6 |
| —— | 1138675-27-0 | C17H14F3N5O4S | |
| —— | 669076-75-9 | C17H23NO3*ClH | |
| —— | potassium salt of (2,3-dihydro-2,2-dimethylbenzofuran-7-yl)hydrazinosulfonic acid | 82277-71-2 | C10H13N2O4S*K |
| —— | Acetic acid 1-(3-methyl-2,3-dihydro-benzofuran-2-yl)-vinyl ester | 125812-18-2 | C13H14O3 |
| —— | 2,3-dihydro-2,2,4,6,7-pentamethyl-3-<(4-methylpiperazino)methyl>-1-benzofuran-5-ol dihydrochloride | 153490-71-2 | C19H30N2O2*2ClH |
| —— | [2,4-Bis-benzyloxy-6-methoxy-benzofuran-(3Z)-ylidene]-acetaldehyde | 30694-04-3 | C25H22O5 |
| —— | 7,8,9,10-tetrachloro-1,1,4,4-tetraphenyl-benzo[b][1,2]diazeto[1,2-d][1,4,5]oxadiazepine-2,5-dione | 90116-20-4 | C34H20Cl4N2O3 |
| —— | 2-(1-Hydroxy-1-methyl-ethyl)-6,7-dimethyl-2,3-dihydro-benzofuran-5-ol | 31604-81-6 | C13H18O3 |
| —— | Acetic acid 4-methyl-2-(6-methyl-4-methylene-chroman-3-yl)-phenyl ester | 104847-87-2 | C20H20O3 |
| —— | 6-(1-Diethylamino-4-pentylamino)-2,3-dihydro-2,2-dimethyl-benzofuran | 31010-98-7 | C19H32N2O |
| —— | 5-bromo-2,3-dihydro-2,2-dimethyl-7-(4-bromo-butoxy)-benzofuran | 1089210-23-0 | C14H18Br2O2 |
| —— | 2-<1,2-Epoxy-1-chlormethyl-aethyl>-2,3-dihydro-benzofuran | 1012-45-9 | C11H11ClO2 |
| —— | [(3S)-6-({(3S)-7-[4-(cyclopentylmethoxy)-2,6-dimethylphenyl]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-48-3 | C32H35NO5 |
| —— | 5-chloro-N,N-dimethyl-8-nitrochroman-3-carboxamide | 1269695-69-3 | C12H13ClN2O4 |
| —— | 1,10-Dimethoxy-5a,10b-dimethyl-5a,10b-dihydro-benzo[b]benzo[4,5]furo[3,2-d]furan | 105314-92-9 | C18H18O4 |
| —— | 2,3-dihydro-2,2-dimethyl-7-hydroxy-benzofuran-5-sulfonic acid N-isopropyl-amide | 1089210-12-7 | C13H19NO4S |
| —— | 2,3-dihydro-2,4-dimethylbenzofuran-7-carboxylic acid | 1189819-01-9 | C11H12O3 |
| —— | (5aR,7R,8S,10S,10aS)-4-methoxy-8-(methoxymethoxy)-10a-vinyl-5a,7,8,9,10,10a-hexahydro-6H-7,10-methanocyclohepta[b]benzofuran-6-one | 358753-70-5 | C19H22O5 |
| —— | (R)-N-(6-benzyloxy-2,3-dihydrobenzofuran-3-yl)hydroxylamine (S)-mandelate | 162750-12-1 | C8H8O3*C15H15NO3 |
| —— | 2,6-Di-tert-butyl-4-(4,7-di-tert-butyl-benzo[1,3]dioxol-2-yl)-phenol | 51786-65-3 | C29H42O3 |
| —— | 5-methyl-2-(4,6,7-trimethyl-2,3-dihydro-1-benzofuran-3-yl)pyridine | 820258-75-1 | C17H19NO |
| —— | 2H,3H-3-(2-ethyl-2-hydroxybutyl)benzofuran | 130013-30-8 | C14H20O2 |
| —— | 3-Phenyl-2,3-dihydro-benzofuran-3-carboxylic acid 2-azepan-1-yl-1-methyl-ethyl ester | 96456-60-9 | C24H29NO3 |