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 |
|---|---|---|---|
| —— | (R)-10-Methyl-7-methylene-3-pentyl-6,7,7a,8,9,11a-hexahydro-5-oxa-dibenzo[a,c]cyclohepten-1-ol | 81780-82-7 | C21H28O2 |
| —— | 1334064-28-6 | C21H28N2O3S | |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-N-cyclohexyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488125-82-2 | C23H25Cl3N2O |
| —— | 4-piperazin-1-yl-7-(2,2,2-trifluoroethoxy)-3,4-dihydro-2H-1-benzopyrane | 1313034-60-4 | C15H19F3N2O2 |
| —— | (1R,3R,4S,5R)-3-[3-[5a-(3,4-dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[3,2-b][1,4]benzodioxin-9-yl]prop-2-enoyloxy]-1-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxycyclohexane-1-carboxylic acid | 1219698-64-2 | C40H32O19 |
| —— | 1334061-93-6 | C22H28N2O3S | |
| —— | cis-2-nitro-3-hydroxy-6-ethoxy-2,3-dihydrobenzo(b)furan | 96089-33-7 | C10H11NO5 |
| —— | cis-1-oxo-3a-hydroxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopenta<b>benzo<b>furan | 72229-56-2 | C12H12O3 |
| —— | (4-Amino-2,3-dihydrobenzofuran-2-yl)methanol | 1002129-62-5 | C9H11NO2 |
| —— | 8-methyl-6-(3,3,4,4,5,5,6,6,6-nonafluorohexylsulfanylmethyl)-4H-1,3-benzoxathiine | 1192176-22-9 | C16H15F9OS2 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-(isopropyl)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-05-2 | C20H21Cl2NO |
| —— | (+/-)-2-(2-bromoethyl)-2,3-dihydro-4,6,7-trimethyl-5-benzofuranol acetate | 154954-20-8 | C15H19BrO3 |
| —— | rac-2,3-dihydro-benzofuran-4-carboxylic acid {3-[5-(3,4-difluoro-phenyl)-2-methyl-thiazole-4-carbonyl]-thiazolidin-2-ylmethyl}-amide | 1204584-66-6 | C24H21F2N3O3S2 |
| —— | 6-methoxy-3-(4-methoxy-phenyl)-2-methyl-2,3-dihydro-benzofuran-5-ol | 37674-34-3 | C17H18O4 |
| —— | 5-formyl-2(S)-(isopropyl-1'-ol)-2,3-dihydrobenzofuran | 115699-94-0 | C12H14O3 |
| —— | 6,7-Dichloro-5-(2-dimethylthiocarbamoyl-acetyl)-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester | 126200-55-3 | C16H17Cl2NO4S |
| —— | 2-(4,8-diacetylbenzo[1,2-d:4,5-d']bis[1,3]dioxol-2-yl)-N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]acetamide | 1338930-54-3 | C20H18N2O9 |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-6-isopropoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-59-6 | C20H21Cl2NO2 |
| —— | [(4S)-4-methyl-4-[(E)-3-phenylprop-2-enyl]chromen-3-yl] 2,2-dimethylpropanoate | 1134202-94-0 | C24H26O3 |
| —— | 1-(2,3-dihydro-benzofuran-3-yl)-3-methanesulfinyl-2-phenyl-propan-2-ol | 63755-74-8 | C18H20O3S |
| —— | 1,3,3-trimethyl-4-(azidomethyl)-9'-hydroxyspiro[indoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine] | 1275613-69-8 | C23H21N5O2 |
| —— | 3-(3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran | 820258-72-8 | C18H20O2 |
| —— | 3-ethoxy-5-methoxy-1-(4-methoxyphenyl)-1-methyl-1,3-dihydroisobenzofuran | 1609472-27-6 | C19H22O4 |
| —— | Acetamide, N-(8-bromo[1]benzopyrano[4,3-c]pyrazol-3-yl)- | 72599-30-5 | C12H8BrN3O2 |
| —— | 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (2,6-dimethylmorpholinosulfenyl)(methyl)carbamate | 55285-06-8 | C18H26N2O4S |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-N,N-dipropyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488127-02-2 | C23H27Cl3N2O |
| —— | 1',2',3',5',6',8',9',9a'-octahydro-3H-spiro[benzofuran-2,7'-pyrrolo[1,2-a]azepine]-5-carbaldehyde | 1258431-58-1 | C17H21NO2 |
| —— | (2-(aminomethyl)-7,8-dihydro-2H-1,6,9-trioxa-9a-borabenzo[cd]azulene-8,8-diyl)dimethanol hydrochloride | 1444766-42-0 | C12H16BNO5*ClH |
| —— | 2,3-Dihydro-2-morpholino-2,3-pentamethylen-5-hydroxy-benzofuran | 5207-25-0 | C17H23NO3 |
| —— | 5,7-ditert-butyl-3-[4-(dimethylamino)phenyl]-3H-1-benzofuran-2-one | 1284257-24-4 | C24H31NO2 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-6-butoxy-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488126-70-1 | C21H22Cl3NO2 |
| —— | cis-3-oxo-1,2,3a,8b-tetrahydro-3a-ethyl-6,8b-dimethyl-3H-cyclopenta<b>benzofuran | 138629-72-8 | C15H18O2 |
| —— | 6-chloro-2,3-dihydro-benzofuran-2-carboxylic acid | 26018-49-5 | C9H7ClO3 |
| —— | 2,9-Dimethyl-5a,10b-dihydro-benzfuro<2,3-b>benzofuran | 10171-65-0 | C16H14O2 |
| —— | 2-n-propoxy-2,3-dihydro-3-methylenebenzofuran | 1187956-10-0 | C12H14O2 |
| —— | 2,3-dihydrobenzofuran-3,7-diol | 1404230-43-8 | C8H8O3 |
| —— | 5-[2-(4-Chloro-phenyl)-2-methoxy-ethyl]-2-methoxy-2,4-dimethyl-2,3-dihydro-benzo[b]oxepine | 77961-17-2 | C22H25ClO3 |
| —— | 2-Methoxy-5-(2-methoxy-2-phenyl-ethyl)-2,4-dimethyl-2,3-dihydro-benzo[b]oxepine | 77961-16-1 | C22H26O3 |
| —— | (1R,3R,4S,5R)-1-[3-[5a-(3,4-dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[3,2-b][1,4]benzodioxin-9-yl]prop-2-enoyloxy]-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxycyclohexane-1-carboxylic acid | 1219698-66-4 | C40H32O19 |
| —— | 1-[4-(2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1,5,6,7-tetrahydroindol-4-one | 849353-12-4 | C23H26F3NO3 |
| —— | (Z)-4-[7-Methoxy-2-methyl-chroman-(4E)-ylidene]-but-2-enoic acid methyl ester | 37977-17-6 | C16H18O4 |
| —— | 1,2,3,4,6,6a-Hexahydrobenzofuro-<3,2-c>-indol-10-ol | 36860-37-4 | C14H15NO2 |
| —— | methyl 1,2-dihydroazuleno<1,2-b>furan-9-carboxylate | 106183-65-7 | C14H12O3 |
| —— | 6,7-Dichloro-5-((E)-3-dimethylamino-3-methylsulfanyl-acryloyl)-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester | 126201-01-2 | C17H19Cl2NO4S |
| —— | (2S,3S,4R)-4-[[(cyanoimino)phenoxymethyl]amino]-6-methoxycarbonyl-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-1-benzopyran | 335382-55-3 | C23H25N3O7 |
| —— | (+/-)-1-cyclopropyl-N-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}methanamine | 852121-91-6 | C19H18Cl2FNO |
| —— | rac-2,3-dihydro-furo[2,3-b]pyridine-3-carboxylic acid 2-chloro-4-fluoro-benzylamide | 1448335-51-0 | C15H12ClFN2O2 |
| —— | 2-(4-((7-bromo-2,3-dihydrobenzofuran-3-yl)oxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1404230-47-2 | C20H22BBrO4 |
| —— | 3-<2,3-Dihydro-benzofuranyl-(6)-oxy>-crotonsaeure-methylester | 107625-47-8 | C13H14O4 |
| —— | 6'-bromodispiro[cyclopropane-1,3'-chroman-4',4"-imidazolidine]-2",5"-dione | 1311265-20-9 | C13H11BrN2O3 |