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-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl acetate | 1089210-07-0 | C12H13ClO3 |
| —— | 5-(benzyloxy)-2-[[[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]thio]methyl]pyridin-4(1H)-one | 1005200-66-7 | C23H19N3O4S |
| —— | 8-(2,6-difluoro-4-chlorophenyl)-6-ethoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488125-55-9 | C19H18ClF2NO2 |
| —— | prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2R,3S)-2-ethenyl-6-(3-hydroxypropoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate | 1016896-74-4 | C24H26BrNO5 |
| —— | 1440969-29-8 | C15H18O3 | |
| —— | 2-Methoxy-3-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-vinyl-2,3-dihydro-benzofuran | 321527-41-7 | C23H27BO4 |
| —— | tert-Butyl-dimethyl-[1-methyl-1-(3,4,7-trimethoxy-3H-inden-1-yl)-propoxy]-silane | 128176-52-3 | C22H36O4Si |
| —— | 6-methyl-spiro[benzofuran-3,1'-cyclopentane]-2,2'-dicarboxylic acid diethyl ester | 860418-94-6 | C19H24O5 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(4-thiazolylmethyl)thio]-1,3,4-oxadiazole | 1005200-52-1 | C14H11N3O2S2 |
| —— | 2,3,3a,8a-tetrahydro-4,6-dimethoxyfuro<2,3-b>benzofuran | 95592-76-0 | C12H14O4 |
| —— | (4a'S,9a'S)-2-amino-7'-(5-chloropyridin-3-yl)-1',2',3',4',4a',9a'-hexahydro-5H-spiro[oxazole-4,9'-xanthen]-2'-ol | 1379805-84-1 | C20H20ClN3O3 |
| —— | dihydroisocorylifonol | 145039-57-2 | C13H16O4 |
| —— | 6-[6-(cyclopropylmethoxy)-2,3-dihydro-1-benzofuran-2-yl]pyridin-3-ol | 1380068-77-8 | C17H17NO3 |
| —— | Acetic acid (S)-2-acetoxy-1-{(R)-5-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,3-dihydro-benzofuran-2-yl}-1-methyl-ethyl ester | 850312-59-3 | C23H36O6Si |
| —— | 2-(2,4-difluorophenyl)-5-(hydroxymethyl)-N-methyl-9-methylsulfonyl-5,6,7,8-tetrahydrofuro[3,2-h][1]benzazepine-3-carboxamide | 1374229-76-1 | C22H22F2N2O5S |
| —— | 2,3,8,9-tetrakis[2-(tert-butyldimethylsilyloxy)ethoxy]-5-hydroxy-11,12-didehydro-5,6-dihydrodibenzo[a,e][8]annulene | 1443674-41-6 | C48H84O9Si4 |
| —— | 2-butyl-2,3-dihydrobenzofuran | 109209-69-0 | C12H16O |
| —— | (R)-2-butyl-2,3-dihydrobenzofuran | 1372790-92-5 | C12H16O |
| —— | 5,7-Diiodo-6-methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-4-ol | 128033-19-2 | C11H10I2O4 |
| —— | methyl 2-<2-(4,5-dimethoxy-3(R)-methyl-2,3-dihydrobenzofuran-6)yl-2,6,6-trimethylcyclohexyl>ethanoate | 99050-64-3 | C23H34O5 |
| —— | 3-(2-(allyloxy)benzyl)-2,3-dihydrobenzofuran | 1242412-59-4 | C18H18O2 |
| —— | 2,3-dihydro-benzofuran-2-carboxylic acid {5-[3-(5-chloro-thiophen-2-ylmethyl)-ureido]-[1,2,4]thiadiazol-3-ylmethyl}-methyl-amide | 1108711-32-5 | C19H18ClN5O3S2 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[[4-(methylsulfonyl)benzyl]thio]-1,3,4-oxadiazole | 1005200-62-3 | C18H16N2O4S2 |
| —— | (3R,4aS,9bS)-9-dimethylaminomethyl-6-methoxy-3,4,4a,9b-tetrahydro-9b-vinyl-dibenzofuran-3-ol | 934162-74-0 | C18H23NO3 |
| —— | 14-(4-fluorophenyl)-N,2-dimethyl-9-methylsulfonyl-13-oxa-3,4,5,9-tetrazatetracyclo[8.7.0.03,7.012,16]heptadeca-1(10),4,6,11,14,16-hexaene-15-carboxamide | 1374230-35-9 | C22H20FN5O4S |
| —— | 2-azidomethyl-6-chloro-4-(2,5-difluoro-phenyl)-benzo[1,3]dioxole | 913630-40-7 | C14H8ClF2N3O2 |
| —— | 3-{6-{[(2,6-dichloro-4-methylphenyl)methyl] sulfanyl}-2H-spiro[1-benzofuran-3,4'-piperidine]-1'-yl}-2-methylpropanoic acid hydrochloride | 1355085-41-4 | C24H27Cl2NO3S*ClH |
| —— | 6-Chloro-7-fluoro-2,3-dihydro-1-benzofuran-3-carboxylic acid | 2137604-00-1 | C9H6ClFO3 |
| —— | 2-[(2,3-dichlorobenzyl)thio]-5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole | 1005200-55-4 | C17H12Cl2N2O2S |
| —— | 7-[[[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]thio]methyl]-5H-thiazolo[3,2-a]pyrimidin-5-one | 1005200-70-3 | C17H12N4O3S2 |
| —— | 3-Amino-2,3-dihydro-1-benzofuran-6-carbonitrilehydrochloride | 2580249-37-0 | C9H9ClN2O |
| —— | 3-Benzyloxy-1,6,6-trimethyl-6,7-dihydro-9H-5-oxa-9-aza-benzocycloheptene-8-thione | 144537-66-6 | C19H21NO2S |
| —— | 8-(2,4,6-trichlorophenyl)-6-propyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]-pyridine | 488124-97-6 | C20H20Cl3NO |
| —— | 2,2,4-trimethyl-2,3-dihydrobenzofuran-5-carboxylic acid | 1126854-74-7 | C12H14O3 |
| —— | (4aSR,9RS,9aSR)-5-methoxy-9-(nitromethyl)-2,3,4,4a,9,9a-hexahydro-1H-xanthene | 1393376-82-3 | C15H19NO4 |
| —— | 8-(2,4-dichlorophenyl)-6-piperidin-1-yl-1,2,3,4,4a,9b-hexahydro[1]benzofuro[3,2-c]pyridine | 488125-63-9 | C22H24Cl2N2O |
| —— | Allyl-(7-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-amine | 62035-29-4 | C13H17NO2 |
| —— | Zr2(μ-OEt)2(HOEt)2(2,3-dihydro-2,2-dimethyl-7-benzofuran(1-))6 | 1034136-11-2 | C68H88O16Zr2 |
| —— | benzyl 4-{6-[2-{[2-(isopropylamino)ethyl]amino}-4-(methylsulfonyl)phenyl]-4H-1,3-benzodioxin-2-yl}piperidine-1-carboxylate trifluoroacetate | 1200572-77-5 | C2HF3O2*C33H41N3O6S |
| —— | 3-ethyl-5-methyl-2,3-dihydro-benzofuran | 104175-12-4 | C11H14O |
| —— | Methyl 2-[6-(quinolin-8-ylmethoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate | 1030847-22-3 | C21H19NO4 |
| —— | 7-Acetoxy-6-brom-1,1',3,3',4,4'-hexamethyl-1,7'-epoxy-2,1'-biinden | 73057-19-9 | C26H29BrO3 |
| —— | trans-2-Acetoxy-3-brom-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran | 72933-08-5 | C12H11BrO4 |
| —— | (R)-3-tert-Butylamino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran | 169758-96-7 | C14H20FNO2 |
| —— | 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (methyl)(4-methylpiperidinosulfenyl)carbamate | 55285-08-0 | C18H26N2O3S |
| —— | N-(4-chlorophenyl)-2,3-dihydrobenzofuran-3-amine | 126884-71-7 | C14H12ClNO |
| —— | 2,5-dioxopyrrolidin-1-yl 2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)acetate | 1394822-10-6 | C19H27NO6Si |
| —— | 5-[1-(3-Phenyl-2,3-dihydro-benzofuran-5-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione | 109208-92-6 | C18H13NO3S |
| —— | (3aS,8bR)-6-methoxy-8-phenylmethoxy-1,2,3a,8b-tetrahydrofuro[2,3-b][1]benzofuran | 193224-00-9 | C18H18O4 |
| —— | 2-[[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]thio]-N,N-diethylacetamide | 1005200-68-9 | C16H19N3O3S |