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-bromo-2-vinyl-2,3-dihydrobenzofuran | 936734-86-0 | C10H9BrO |
| —— | 2H,3H-3-((1-hydroxy-2-methylcyclohexyl)methyl)benzofuran | 130013-34-2 | C16H22O2 |
| —— | 8-(2,6-difluoro-4-chlorophenyl)-6-(butylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488125-32-2 | C21H22ClF2NOS |
| —— | 2-[(2S)-6-methoxy-2,3-dihydro-1-benzofuran-2-yl]propan-2-yl acetate | 239445-77-3 | C14H18O4 |
| —— | (1S)-1-[(2R,3aS,8bS)-8-ethyl-2,3,3a,8b-tetrahydrofuro[3,2-b][1]benzofuran-2-yl]prop-2-yn-1-ol | 82064-82-2 | C15H16O3 |
| —— | methyl 2-((3S)-6-(((trifluoromethyl)sulfonyl)oxy)-2,3-dihydrobenzofuran-3-yl)acetate | 1258399-02-8 | C12H11F3O6S |
| —— | (+/-)-2-(azidomethyl)-7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran | 1072073-15-4 | C13H16ClN3O |
| —— | 10a-(4-(benzyloxy)phenyl)-4-fluoro-6,7,8,9,10,10a-hexahydro-5aH-benzo[b]cyclohepta[d]furan | 1147714-39-3 | C26H25FO2 |
| —— | (+/-)-{[7-fluoro-5-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-66-1 | C16H16FNO |
| —— | 8-(2,4,6-trichlorophenyl)-6-butyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine | 488124-99-8 | C21H22Cl3NO |
| —— | (+/-)-{[6-chloro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-90-1 | C16H16ClNO |
| —— | (+/-)-{[7-fluoro-5-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-51-4 | C16H16FNO |
| —— | N-[3-(2-amino-4-methyl-5,6-dihydro-1,3-thiazin-4-yl)-4-fluorophenyl]-2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazole-4-carboxamide | 1075225-86-3 | C23H21FN4O2S2 |
| —— | 2-Acetoxythalliummethyl-cumaran | 60468-46-4 | C13H15O5Tl |
| —— | 5-Bromo-3-(bromomethyl)-2,3-dihydro-1-benzofuran | 2155855-22-2 | C9H8Br2O |
| —— | 2,3-dihydro-3,3-dimethyl-2-methylcarbamoyloxybenzofuran-5-yldimethylaminosulfonate | 57161-70-3 | C14H20N2O6S |
| —— | (+/-)-{[7-(2,6-dimethylphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-87-9 | C19H23NO |
| —— | 2,3-dihydro-3,3-dimethyl-2-ethylcarbamoyloxybenzofuran-5-yldiethylaminosulfonate | 57161-74-7 | C17H26N2O6S |
| —— | N-(2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)-2-hydroxy-3-methylbutanamide | 1452477-20-1 | C22H25Cl2NO4 |
| —— | (+/-)-2-(azidomethyl)-6-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran | 852117-97-6 | C16H14FN3O |
| —— | (1R,5S,13R,14S)-10,17-dichloro-3,6,21-trioxahexacyclo[12.7.0.01,5.05,13.07,12.015,20]henicosa-7(12),8,10,15(20),16,18-hexaene-2,4-dione | 67324-81-6 | C18H8Cl2O5 |
| —— | (3aR,11bS)-3-methyl-2,3,3a,4,5,6-hexahydrobenzofuro[3,2-d]indol-6a(1H)-ol | 88755-04-8 | C15H19NO2 |
| —— | 2,6-Dimethoxy-4-methoxymethoxy-3-methyl-2,3-dihydro-benzofuran-3-ol | 129750-77-2 | C13H18O6 |
| —— | (+/-)-{[5-fluoro-7-(2-methoxy-5-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-55-1 | C18H20FNO2 |
| —— | 6,7-Dichloro-5-((E)-3-ethylamino-2-methyl-3-methylsulfanyl-acryloyl)-2,3-dihydro-benzofuran-2-carboxylic acid | 126200-46-2 | C16H17Cl2NO4S |
| —— | 2-Aethyl-3,4-butano-2,3-dihydro-benzofuran | 97438-31-8 | C14H18O |
| —— | [(1R,2R,6S,7R,9R)-1-[2-(dimethylamino)-2-oxoethyl]-12-methoxy-4,4-dimethyl-3,5,10-trioxatetracyclo[7.7.0.02,6.011,16]hexadeca-11(16),12,14-trien-7-yl] acetate | 1256603-64-1 | C22H29NO7 |
| —— | 2-((1R,2S,3S,4R,4aS,9bS)-2,3-dihydroxy-6-methoxy-2,3,4,4a-tetrahydro-1,4-epoxydibenzo[b,d]furan-9b(1H)-yl)-N,N-dimethylacetamide | 1256603-61-8 | C17H21NO6 |
| —— | 2-[(1S,2R,6S,7S,8S,9S)-8,14-dibromo-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 | 1256603-62-9 | C20H25Br2NO6 |
| —— | 1-((R)-5-Benzyloxy-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-3-ylmethyl)-4-methyl-piperazine | 188061-18-9 | C26H36N2O2 |
| —— | 4-formyl-5-hydroxy-δ9,9a-1,2-dihydro-3H-xanthene | 75830-33-0 | C14H14O3 |
| —— | (1R,3R)-3-(2,3-Dihydro-benzofuran-4-yl)-2,2-dimethyl-cyclopropanecarboxylic acid methoxy-methyl-amide | 665004-03-5 | C16H21NO3 |
| —— | methyl (S)-6,7-dichloro-5-(N,N-dimethylsulfamoyl)-2,3-dihydrobenzo<b>furan-2-carboxylate | 118166-30-6 | C12H13Cl2NO5S |
| —— | 5-methoxy-4-(2-nitro-1-propenyl)-2,3-dihydrobenzofuran | 130933-07-2 | C12H13NO4 |
| —— | (1s,4s)-5‘-bromo-4’‘-fluoro-4-methoxydispiro[cyclohexane-1,2’-[1]benzofuran3’,2’‘-pyrrol]-5”-amine | 1430422-21-1 | C17H18BrFN2O2 |
| —— | (+/-)-4aα-Hydroxy-6-methoxy-9-chloro-9bβ-<2-(formylamino)ethyl>-1,2,3,4,4aβ,9b-hexahydrodibenzofuran | 90149-45-4 | C16H20ClNO4 |
| —— | (+/-)-2-(azidomethyl)-7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran | 1072073-44-9 | C15H12FN3O |
| —— | 2,3-Dihydro-4-bromo-6-propyl-5-benzofuranol methoxymethyl ether | 119795-43-6 | C13H17BrO3 |
| —— | 2,4-Dimethyl-4-aethoxycarbonyl-chromanon-(3) | 92252-19-2 | C14H16O4 |
| —— | 2-cyclohexyl-4-methyl-1a,3,4,4a-tetrahydrobenzofuro<2,3-e>-1,2-oxazino-3-carbonitrile | 114523-41-0 | C18H22N2O2 |
| —— | 2-(5-Fluoro-2-cyclopropylmethyloxy-1,4-benzo-dioxan-2-yl)-imidazoline Hydrochloride | 313950-89-9 | C15H17FN2O3*ClH |
| —— | 2,7-Dimethoxy-9,10-dioxa-9aλ<sup>4</sup>-thia-indeno[1,2-a]indene | 34303-15-6 | C15H12O4S |
| —— | (+/-)-{[7-(3-methylphenyl)-5-phenyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852125-03-2 | C23H23NO |
| —— | 134647-15-7 | C20H29NO3 | |
| —— | (+/-)-{[7-fluoro-5-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-55-8 | C16H16FNO2 |
| —— | (+/-)-N-{[7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}cyclopropanamine | 852123-78-5 | C18H17Cl2NO |
| —— | 4,5-dimethoxy-2-(4,4-diphenyl-1,4-dihydro-2H-3,1-benzoxazin-2-yl)benzoic acid | 1242190-25-5 | C29H25NO5 |
| —— | 4-Benzyliden-6-ethoxy-2,3,4,4a-tetrahydro-1H-dibenzofuran-9b-propionsaeure | 97081-79-3 | C24H26O4 |
| —— | 3-[[4-[2-[1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yl]-2-methyl-3H-1-benzofuran-5-yl]-3,6-dihydro-2H-pyridin-1-yl]sulfonyl]propan-1-ol | 1346529-45-0 | C29H38N4O4S |
| —— | 1-(6-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl)-4-(methoxymethoxy)but-2-yn-1-ol | 1058196-54-5 | C25H38O7Si |