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 |
|---|---|---|---|
| —— | 7-Chloro-5-chloromethyl-2,3-dimethyl-2,3-dihydro-benzofuran | 57899-15-7 | C11H12Cl2O |
| —— | 1-[1,3]Dioxolan-2-yl-6-methyl-11-oxa-tricyclo[6.2.1.0<sup>2,7</sup>]undeca-2(7),3,5-triene | 59907-24-3 | C14H16O3 |
| —— | (1'RS)-7-[1'-benzyloxy-(2'-iodo-3'-methoxyphenyl)-methyl]-6-methoxy-2,2-dimethyl-8-vinyl-4H-benzo[1,3]dioxine | 808750-13-2 | C28H29IO5 |
| —— | 5-(3,4-dimethyl-phenoxymethyl)-8-methoxy-3-methyl-2,3-dihydro-benzo[<i>f</i>][1,4]oxazepine | 47353-19-5 | C20H23NO3 |
| —— | 2-[2-(6,7-Dichloro-2-methoxycarbonyl-2,3-dihydro-benzofuran-5-yl)-2-oxo-ethylsulfanyl]-3-methyl-thiazol-3-ium; bromide | 126200-91-7 | Br*C16H14Cl2NO4S2 |
| —— | (4aS,9bR)-4-[1-Hydroxy-meth-(Z)-ylidene]-8,9b-dimethyl-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one | 86658-16-4 | C15H16O3 |
| —— | 5-Methoxy-2-octyl-2,3-dihydrobenzofuran | 172083-59-9 | C17H26O2 |
| —— | (4aS,9bR)-4-[1-Dibenzylamino-meth-(E)-ylidene]-8,9b-dimethyl-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one | 86657-96-7 | C29H29NO2 |
| —— | 8-methoxy-5-(3-methoxy-phenoxymethyl)-3-methyl-2,3-dihydro-benzo[<i>f</i>][1,4]oxazepine | 47353-20-8 | C19H21NO4 |
| —— | rotenone 6'-norketone enol acetate | 23295-59-2 | C24H22O8 |
| —— | 3,4-dihydro-3-(5-(thiazol-2-yl)-1,2,4-oxadiazol-3-yl)-N-((thiazol-2-yl) methylene)-2H-chromen-2-amine | 1384471-89-9 | C18H13N5O2S2 |
| —— | Ethyl 2-(cyanomethyl)-2-methyl-2,3-dihydrobenzofuran-5-carboxylate | 1372769-17-9 | C14H15NO3 |
| —— | 4-[2-[3,5-dichloro-2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxymethyl]-6-oxopyridin-1-yl]ethyl]benzoic acid | 1091596-42-7 | C25H23Cl2NO5 |
| —— | Methyl 2-[4-(azidomethyl)-7-methoxy-2-oxo-3-(3-oxobutyl)-1-benzofuran-3-yl]acetate | 1186481-47-9 | C17H19N3O6 |
| —— | (+/-)-{[7-(2,6-dimethylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852121-88-1 | C17H18FNO |
| —— | 3-Phenyl-2,3-dihydro-benzofuran-3-carbonsaeure-(1-methyl-piperidyl-(4)-ester) | 94918-08-8 | C21H23NO3 |
| —— | ethyl 2-(chloromethyl)-2-hydroxy-7-(prop-2-en-1-yloxy)-2H-1-benzopyran-3-carboxylate | 1278587-66-8 | C16H17ClO5 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-(ethylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-39-2 | C19H18Cl3NOS |
| —— | (1R,4aR,9aR)-6-nitro-2-(2-phenethyl)-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridine | 1058712-91-6 | C22H24N2O3 |
| —— | [(3S)-6-({(3S)-7-[(4-methylpyridin-2-yl)amino]-2,3-dihydro-1-benzofuran-3-yl}amino)-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-67-6 | C24H23N3O4 |
| —— | 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl N-(2-ethylsulphinylethoxycarbonyl)-N-methyl-carbamate | 77248-91-0 | C17H23NO6S |
| —— | (4aS,9bR)-4-[1-Dipropylamino-meth-(E)-ylidene]-8,9b-dimethyl-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one | 86657-94-5 | C21H29NO2 |
| —— | 2,2,6,7-tetramethyl-3-(4-propan-2-ylphenyl)-3H-1-benzofuran-5-amine | 821766-96-5 | C21H27NO |
| —— | (S)-(-)-5-hydroxy-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-carboxylic acid | 118100-79-1 | C13H16O4 |
| —— | tert-butyl 4-(7-fluoro-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)-2,3-dihydrobenzofuran-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate | 1346529-67-6 | C30H39FN4O3 |
| —— | (4aS,9bR)-8-(2,6-difluoro-4-chlorophenyl)-6-cyclohexyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-26-7 | C23H24ClF2NO |
| —— | oxo-3 fluoro-6 N,N dimethylcarboxamidomethyl-9b β hexahydro-1,2,3,4,4a,9b dibenzofuranne | 126412-29-1 | C16H18FNO3 |
| —— | cis-3,10-di-tert-butyl-5,5a,6,7,7a,8-hexahydrocyclopenta[1,2-b:1,5-b']dichromene-1,12-diol | 1442637-36-6 | C27H34O4 |
| —— | 4-Hydroxy-2-<1-hydroxy-aethyl>-cumaran | 99186-36-4 | C10H12O3 |
| —— | 6,7,6',7'-Tetramethyl-3,3'-diphenyl-3H,3'H-[3,3']bibenzofuranyl-2,2'-dione | 65425-09-4 | C32H26O4 |
| —— | 1310431-51-6 | C26H31N5O3 | |
| —— | N-<2,3-dihydro-4,7-dimethoxy-6-(2-piperidinoethoxy)-5-benzofuranyl>acetamide | 75884-16-1 | C19H28N2O5 |
| —— | 2-(2-Methyl-2-nitro-propyl)-2,3-dihydro-benzofuran | 83577-42-8 | C12H15NO3 |
| —— | 3-Chloro-N-((4aS,9bS)-8,9b-dimethyl-3-oxo-3,4,4a,9b-tetrahydro-dibenzofuran-2-yl)-propionamide | 61133-01-5 | C17H18ClNO3 |
| —— | 2,3-dihydro-2-isopropyl-2-methyl-5-nitrobenzofuran | 1236305-76-2 | C12H15NO3 |
| —— | (2-(2,3-dihydro-2-methyl-5-nitrobenzofuran-2-yl)ethoxy)triisopropylsilane | 1236305-80-8 | C20H33NO4Si |
| —— | 916509-79-0 | C21H29NO2 | |
| —— | N-(6"-bromodispiro[1,3-dioxolane-2,1'-cyclohexane-4',2"-inden]-1"(3"H)-ylidene)-2-methylpropane-2-sulfinamide | 1383986-04-6 | C20H26BrNO3S |
| —— | N-benzyl-3-(4-isopropylphenyl)-2,3-dihydro-1-benzofuran-5-amine | 820257-39-4 | C24H25NO |
| —— | 4-(4-fluoro-6,7,8,9,10,10a-hexahydro-5aH-benzo[b]cyclohepta[d]furan-10a-yl)phenol | 1147714-42-8 | C19H19FO2 |
| —— | 2-(3-Methoxy-propylaminomethyl)-2,3-dihydrobenzofuran | 17793-80-5 | C13H19NO2 |
| —— | 2,3-dihydro-benzofuran-7-carboxylic acid [3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-oxazolidin-2-ylmethyl]-amide | 1220346-85-9 | C25H25N3O4S |
| —— | 5-{2-methoxy-6-[2-(4-trifluoromethoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-2,3-dihydro-benzofuran-2-carboxylic acid hydrochloride | 885069-02-3 | C23H20F3N3O5*ClH |
| —— | 6-(3-phenoxypropyl)-5-phenylmethoxy-2,3-dihydro-1-benzofuran | 119795-53-8 | C24H24O3 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-(methylthio)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-38-1 | C18H16Cl3NOS |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-(benzyloxy)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-74-5 | C24H20Cl3NO2 |
| —— | (3,5-di-t-butyl-1,2-benzenediolato(2-)-O,O`)oxobis(hydroxyldibenzylamido(1-)-O,N)molybdenum(VI) | 111264-38-1 | C42H48MoN2O5 |
| —— | 1331858-25-3 | C15H18O2 | |
| —— | 2,2-dimethyl-2,3-dihydro-benzofuran-7-carboxylic acid [3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-oxazolidin-2-ylmethyl]-amide | 1220346-86-0 | C27H29N3O4S |
| —— | 5,7,8-trimethyl-2-tetradecylchroman-6-ol | 1159426-24-0 | C26H44O2 |