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-methyl-2,3-dihydro-benzofuran-7-yl)-acetic acid amide | 99854-84-9 | C11H13NO2 |
| —— | 6a-acetoxy-3,4,9,10-tetramethoxy-6,6a,7,11b-tetrahydro-indeno[2,1-c]chromene | 100736-31-0 | C22H24O7 |
| —— | 3-(2-(1,3-dioxolan-2-yl)ethyl)-3-(2-(1,1,2,2,2-pentamethyldisilaneyl)phenyl)cyclobutan-1-one | 1379534-79-8 | C20H32O3Si2 |
| —— | allyl (2R,3S)-2-((benzylamino)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydro benzofuran-3-ylcarbamate | 1592908-67-2 | C24H30N2O6 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-(2-propylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-32-5 | C20H21Cl2NOS |
| —— | cis-1-oxo-3a,7-dimethoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopenta<b>benzo<b>furan | 72229-60-8 | C14H16O4 |
| —— | 2-Ethoxy-7-hydroxy-4,5-dimethoxy-2,3-dihydrobenzofuran | 176847-03-3 | C12H16O5 |
| —— | ethyl (Z)-2-(2-ethoxy-2-oxoethylidene)-4-hydroxy-6-methoxychromane-4-carboxylate | 1380746-11-1 | C17H20O7 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-N-methyl-N-propyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488125-95-7 | C21H24Cl2N2O |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-methoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-56-3 | C18H17Cl2NO2 |
| —— | ethyl (E)-5-(1-(acetoxyimino)propyl)-7-chloro-6-hydroxy-2,3-dihydrobenzofuran-2-carboxylate | 95635-14-6 | C16H18ClNO6 |
| —— | 5-methyl-2,3-dihydro-benzofuran-7-carboxylic acid amide | 99060-05-6 | C10H11NO2 |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-pyridin-3-ylacetamide | 1048960-25-3 | C24H31N3O2 |
| —— | (4aS,9bR)-8-(2,6-difluoro-4-chlorophenyl)-N-phenyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488125-86-6 | C23H19ClF2N2O |
| —— | 3-(bromomethyl)-6-chloro-2,3-dihydro-1-benzofuran | 711017-71-9 | C9H8BrClO |
| —— | 937254-96-1 | C23H21N3O4 | |
| —— | 1334060-46-6 | C20H26N2O3S | |
| —— | 2,3,6,7-tetrahydro-benzo[1,2-b;4,5-b']difuran-4-carboxylic acid [(1R,3S,4S)-2-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-2-aza-bicyclo[2.2.1]hept-3-ylmethyl]-amide | 1181571-66-3 | C30H31N3O4S |
| —— | 1613234-08-4 | C16H17FO5 | |
| —— | (1S,2R,3aS,8bS)-5,7-dibromo-1-(hydroxymethyl)-2,3,3a,8btetrahydro-1H-cyclopenta[b]benzofuran-2-ol | 1350910-96-1 | C12H12Br2O3 |
| —— | t-butyl 4-(7,8-dichlorochroman-4-yl)piperazine-1-carboxylate | 1313035-77-6 | C18H24Cl2N2O3 |
| —— | (1R,3S)-3-[([(S)-1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-{4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-amino)-methyl]-cyclopentanecarboxylic acid | 1443020-83-4 | C31H38N2O7 |
| —— | 5-bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexan]-3-imine | 1383985-83-8 | C14H16BrNO2 |
| —— | [2-(4-benzylsulfanyl-3,4-dihydro-2H-chromen-3-yl)phenoxy]-tert-butyl-dimethylsilane | 209404-33-1 | C28H34O2SSi |
| —— | methyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7-benzofuranyl]oxy]carbonyl]amino]thio]benzimidate | 93960-92-0 | C20H22N2O4S |
| —— | (S)-tert-butyl 2-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dihydro-1H-benzo[2,3]oxepino[4,5-d]imidazol-2-yl)pyrrolidine-1-carboxylate | 1422428-16-7 | C26H36BN3O5 |
| —— | 8-Oxiranylmethoxy-1,2,3,4,4a,9b-hexahydro-dibenzofuran | 94769-43-4 | C15H18O3 |
| —— | (2R,3S)-3-Methoxy-2-((E)-styryl)-2,3-dihydro-benzofuran | 65769-08-6 | C17H16O2 |
| —— | 5-benzylidene-2,3-dihydro-1-benzofuran-1-ium | 81390-58-1 | C15H13O |
| —— | (+/-)-4,6-Dimethoxy-9-chloro-9bβ-<2-(N-formamido)ethyl>-1,2,4aβ,9b-tetrahydrodibenzofuran | 88304-33-0 | C17H20ClNO4 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-methyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-02-9 | C18H17Cl2NO |
| —— | 2-Octyl-2,3-dihydro-1-benzofuran-5-carboxylic acid | 169892-82-4 | C17H24O3 |
| —— | methyl 2,3-dihydro-2-methylbenzofuran-6-carboxylate | 87513-57-3 | C11H12O3 |
| —— | 8b-methoxy-1,1-dimethyl-2,2a-dihydrocyclobuta[c]chromen-3-one | 77958-95-3 | C14H16O3 |
| —— | (+/-)-{[7-(2-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-74-4 | C17H18ClNO |
| —— | (5S)-5-({[4-(2,3-dihydro-1-benzofuran-5-yl)-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)-5-methylimidazolidine-2,4-dione | 675106-94-2 | C18H21N3O5S |
| —— | 8-chloro-7-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-ol | 1313035-62-9 | C10H8ClF3O2 |
| —— | 2-Octyl-2,3-dihydro-1-benzofuran-5-carbonitrile | 169892-84-6 | C17H23NO |
| —— | trans-2-N-Methyl-anilino-3-chlor-chroman | 36055-14-8 | C16H16ClNO |
| —— | 3,3-Dibrom-4-hydroxy-chroman | 30518-56-0 | C9H8Br2O2 |
| —— | 5-benzyloxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol | 183142-45-2 | C20H24O3 |
| —— | N-(4-Hydroxy-7-methyl-chroman-3-yl)-acetamide | 54444-68-7 | C12H15NO3 |
| —— | methyl 2-[(3E)-3-ethylidene-1-benzofuran-2-yl]acetate | 1440969-22-1 | C13H14O3 |
| —— | 3-methyl-7-trimethylsilyl-2,3-dihydrobenzofuran | 869085-46-1 | C12H18OSi |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-propyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-04-1 | C20H21Cl2NO |
| —— | ethyl 6-methoxy-3-oxochromane-4-carboxylate | 76322-71-9 | C13H14O5 |
| —— | 3-(3,4-dimethoxy-phenyl)-6-hydroxy-3H-benzofuran-2-one | 31542-77-5 | C16H14O5 |
| —— | 4-(2,3-dihydro-benzofuran-6-yl)-cyclohex-3-enone | 1252615-65-8 | C14H14O2 |
| —— | 5-(3-Phenyl-2,3-dihydro-benzofuran-5-ylmethyl)-thiazolidine-2,4-dione | 109209-24-7 | C18H15NO3S |
| —— | methyl 7-[2,3-dihydro-2,2,4-trimethyl-5-methylamino-6-(propan-2-yl)benzo[b]furan-7-yl]-3,5-dihydroxyheptanoate | 149245-49-8 | C23H37NO5 |