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 |
|---|---|---|---|
| —— | [6-(methoxymethoxy)-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl-]methanol | 1612147-04-2 | C14H18O4 |
| —— | 5-fluoro-3H-spiro[benzofuran-2,1'-cyclopentane]-7-carboxylic acid | 1234845-22-7 | C13H13FO3 |
| —— | 2,3-dimethyl-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester | 856180-69-3 | C13H16O3 |
| —— | 1,14-dimethoxy-7,8,16,17-tetrahydrodibenzo[e,m][1,4]dioxa[8,11]diazacyclotetradecine | 1402142-92-0 | C20H22N2O4 |
| —— | (2,2-diethyl-5-fluoro-2,3-dihydrobenzofuran-7-yl)methanol | 1352740-24-9 | C13H17FO2 |
| —— | 5-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran | 820257-35-0 | C19H21BrO |
| —— | 94405-69-3 | C34H46N4O6 | |
| —— | Potassium; 6,7-dichloro-5-diethylsulfamoyl-2,3-dihydro-benzofuran-2-carboxylate | 103968-89-4 | C13H14Cl2NO5S*K |
| —— | (3R,5S)-3,5-dimethyl-7-(trifluoromethoxy)-2,3,4,5-tetrahydro-1,4-benzoxazepine | 1345731-93-2 | C12H14F3NO2 |
| —— | 2,3-dihydro-2,3-dimethyl-3-(phenylthio)benzo<b>furan-2-ol | 135831-70-8 | C16H16O2S |
| —— | 2,3-dimethoxy-2,3-dihydro-benzofuran | 42081-67-4 | C10H12O3 |
| —— | 2,2-dimethyl-5-nitro-7-(3-hydroxy-propoxy)-2,3-dihydro-benzofuran | 1089187-60-9 | C13H17NO5 |
| —— | O-Ethyl-S-n-propyl-O-(5-chloro-2,3-dihydro-2,2-dimethyl-7-benzofuranyl)dithiophosphate | 96408-65-0 | C15H22ClO3PS2 |
| —— | 3,3-dimethyl-7-(2,2-dimethyl-propyl)-5-[(1S,2S)-1,2-methano-1-methyl-3-oxo-propyl]-2,3-dihydro-benzofuran | 623176-13-6 | C20H28O2 |
| —— | aflatoxin D<sub>1</sub> acetate | 124575-30-0 | C18H16O6 |
| —— | (9aS)-8-acetyl-N-{4-[(2,4-dichlorobenzyl)oxy]-2,3,5,6-tetramethylbenzyl}-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925440-86-4 | C35H33Cl2NO8 |
| —— | 2-<(β-Piperidinoethyl)oxy>methyl-2,3-dihydrobenzo<b>furan | 66158-87-0 | C16H23NO2 |
| —— | 2-methyl-chroman-3-ylamine; hydrochloride | 23915-76-6 | C10H13NO*ClH |
| —— | (5-Methoxy-4,6,7-trimethyl-2,3-dihydro-benzofuran-2-yl)-acetyl chloride | 154954-39-9 | C14H17ClO3 |
| —— | (+/-)-2-(azidomethyl)-7-cyclopentyl-2,3-dihydro-1-benzofuran | 852113-07-6 | C14H17N3O |
| —— | 2-(3,5-difluoro-4-((5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)cyclopropanecarboxylic acid | 1234841-66-7 | C21H19F3O4 |
| —— | 3,3-Bis-(4-methoxy-phenyl)-3H-benzofuran-2-one | 137605-06-2 | C22H18O4 |
| —— | 3-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-2-methoxyphenyl)-2-methylpropanoic acid | 1234841-91-8 | C22H25ClO5 |
| —— | 5-chloro-2,3-dihydro-2,3-dimethyl-2,3-epoxybenzofuran | 136795-96-5 | C10H9ClO2 |
| —— | rac-(1-((3R,3aS,5R,5aS,10bR,10cR)-3-methoxy-3,3a,4,5a,10b,10c-hexahydro-5H-3,5-epoxyindeno[5,4-b]benzofuran-5-yl)vinyl)trimethylsilane | 73961-68-9 | C21H26O3Si |
| —— | 1-{[3-(6-methyoxy-4H-chromen-3-yl)-1,2,4-oxadiazol-5-yl]methyl}piperidine | 1514898-79-3 | C18H21N3O3 |
| —— | 1416458-45-1 | C20H20F4O2S | |
| —— | 2-<(1-Acetoxymercury)ethyl>-2,3-dihydrobenzofuran | 66865-63-2 | C12H14HgO3 |
| —— | 4-((2R,4R)-2,4-Dimethyl-chroman-4-yl)-phenol | 64681-45-4 | C17H18O2 |
| —— | 2-(4-((5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)benzyl)cyclopropanecarboxylic acid | 1234843-89-0 | C22H23FO4 |
| —— | 6,7-Dichloro-5-{2-[4-oxo-[1,3]thiazinan-(2E)-ylidene]-acetyl}-2,3-dihydro-benzofuran-2-carboxylic acid tert-butyl ester | 126201-06-7 | C19H19Cl2NO5S |
| —— | ethyl (2E)-6-tert-butyl-2-(2-ethoxy-2-oxoethylidene)-4-hydroxy-3H-chromene-4-carboxylate | 1380745-82-3 | C20H26O6 |
| —— | 4-(4-aminofuro[3,2-c]pyridin-2-yl)-2-(4-chlorophenyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carbonitrile | 1309048-43-8 | C21H13ClN4O3 |
| —— | tert-butyl 9-(diethylamino)-3,4,12,12a-tetrahydro-6H-pyrazino[2,1-c][1,4]benzoxazepine-2(1H)-carboxylate | 1000782-41-1 | C21H33N3O3 |
| —— | 1196967-77-7 | C28H33N3O3S | |
| —— | methyl {(3S)-6-[{7-[(2-amino-5-fluorophenyl)amino]-2,3-dihydro-1-benzofuran-3-yl}(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate | 1258399-73-3 | C27H23F4N3O5 |
| —— | 5-methyl-2,3-dihydrobenzo[b]furan-4-ol | 600176-61-2 | C9H10O2 |
| —— | 3-(4-((5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)-2-isopropoxyphenyl)propanoic acid | 1234842-95-5 | C23H27ClO5 |
| —— | (R)-4-(2,3-dihydro-benzofuran-2-yl)-6-(3-methylamino-pyrrolidin-1-yl)-pyrimidin-2-ylamine | 1046449-70-0 | C17H21N5O |
| —— | (5S)-5-[(1S,2R,12R)-14,14-dimethyl-2-phenoxy-13,15-dioxatetracyclo[7.6.0.01,12.03,8]pentadeca-3(8),4,6,9-tetraen-6-yl]-2-(2-phenylethyl)-4,5-dihydro-1,3-oxazole | 1093855-82-3 | C32H31NO4 |
| —— | (S)-4-bromo-2,5-dimethyl-2,3-dihydrobenzofuran-7-amine | 1609171-26-7 | C10H12BrNO |
| —— | (+/-)-2-(azidomethyl)-7-(3-chloro-4-fluorophenyl)-2,3-dihydro-1-benzofuran | 1072073-21-2 | C15H11ClFN3O |
| —— | 3-(2-ethoxy-4-((5-ethoxy-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)propanoic acid | 1352739-70-8 | C24H30O6 |
| —— | (9aS)-8-acetyl-N-(2,4-dimethylbenzyl)-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide | 925439-69-6 | C26H25NO7 |
| —— | 6,7-dichloro-5-(4-oxoperhydro-1,3-thiazin-2-ylidene)acetyl-2,3-dihydro-2-benzo<b>furancarboxylic acid | 105978-87-8 | C15H11Cl2NO5S |
| —— | 4-(4-Methoxy-phenyl)-2-methyl-1,2,3,3a,4,9b-hexahydro-chromeno[3,4-b]pyrrole-1-carboxylic acid methyl ester | 133765-33-0 | C21H23NO4 |
| —— | (R)-9-[3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-2-methyl-2,3,4,5-tetrahydropyrido[2,3-f][1,4]oxazepine | 1383377-48-7 | C19H19FN4O |
| —— | methyl 3-((2R)-2-Prop-2-enyl-2,3-dihydrobenzo[b]furan-4-yl)propanoate | 532399-66-9 | C15H18O3 |
| —— | N-(4-aminothiophen-3-yl)-5-[3-(2,3-dihydro-1-benzofuran-5-yl)-1-(2-dimethylaminoethyl)ureidomethyl]pyridine-2-carboxylic acid amide | 1196981-55-1 | C24H28N6O3S |
| —— | 8-(2,4,6-trichlorophenyl)-6-(cyclohexyloxy)-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488125-51-5 | C23H24Cl3NO2 |