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 |
|---|---|---|---|
| —— | 2,4,4-trimethoxy-2-(4-methylphenyl)-3H-chromen-3-ol | 155723-53-8 | C19H22O5 |
| —— | 1258401-98-7 | C34H34F3NO6S | |
| —— | 2-Methoxy-3-methylen-5-methyl-2,3-dihydrobenzofuran | 65817-15-4 | C11H12O2 |
| —— | 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (methyl)(3-methylpiperidinosulfenyl)carbamate | 55285-10-4 | C18H26N2O3S |
| —— | 9b-Methyl-8-phenyl-4a,9b-dihydro-4H-dibenzofuran-3-one | 68260-93-5 | C19H16O2 |
| —— | ethyl 2-bromo-3-<4-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3-ylmethoxy)phenyl>propanoate | 224954-06-7 | C32H37BrO5 |
| —— | 2,2-Dibenzyl-6,8-ditert-butyl-4-phenyl-3,4-dihydrochromene | 127693-17-8 | C37H42O |
| —— | 2,5-dimethyl-2,3,3-D3-coumaran | 67102-60-7 | C10H12O |
| —— | 6-(2-hydroxypropyl)-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol | 87386-34-3 | C13H18O3 |
| —— | 2-amino-7'-(5-chloropyridin-3-yl)-1',4',4a',9a'-tetrahydro-5H-spiro[oxazole-4,9'-xanthen]-2'(3'H)-one | 1379809-94-5 | C20H18ClN3O3 |
| —— | (6S,7S)-7-[5-(7-benzyl-3,3-dimethyl-2,3-dihydro-benzofuranyl)]-6,7-methano-3-methyl-octa-2E,4E-dienoic acid ethyl ester | 623176-23-8 | C29H34O3 |
| —— | 5-bromo-3-(4-isopropylphenyl)-6,7-dimethyl-2,3-dihydro-1-benzofuran | 820257-31-6 | C19H21BrO |
| —— | diethyl 3-(formylmethyl)-5-methoxybenzofuran-2,2(3H)-dicarboxylate | 1401439-22-2 | C17H20O7 |
| —— | 7,9-Dibromo-4-oxo-4H-pyrano[2,3-b]chromene-2,3,10a-tricarboxylic acid trimethyl ester | 64657-50-7 | C18H12Br2O9 |
| —— | 4,5,6,7-tetramethyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 68255-29-8 | C14H18O3 |
| —— | Methyl 5-bromo-2,3-dihydro-1-benzofuran-2-carboxylate | 1463457-51-3 | C10H9BrO3 |
| —— | [2-((1S,4aS,9bS)-8,9b-Dimethyl-1,2,3,4,4a,9b-hexahydro-dibenzofuran-1-yl)-ethyl]-trimethyl-ammonium; iodide | 68789-16-2 | C19H30NO*I |
| —— | 2,4-diacetoxy-4',6-dimethoxyisoflavan | 95332-30-2 | C21H22O7 |
| —— | 2-aminocarbonylamino-5-(2,3-dihydrobenzofuran-7-yl)pyrrole-3-carboxamide | 1210038-50-8 | C14H14N4O3 |
| —— | N-benzyl-N-(2-(4,5-dihydro-1H-imidazol-2-yl)-2-ethyl-2,3-dihydrobenzofuran-5-yl)-2-(trimethylsilyl)ethane-1-sulfonamide | 1009595-09-8 | C25H35N3O3SSi |
| —— | 1382135-45-6 | C28H34N2O5 | |
| —— | 2,3-dihydro-3,3-dimethyl-7-fluoro-5-trifluoromethanesulfonyloxy benzofuran | 131394-68-8 | C11H10F4O4S |
| —— | (4-Methoxy-2,3,3-trimethyl-2,3-dihydro-benzofuran-6-yl)-acetic acid | 104875-29-8 | C14H18O4 |
| —— | 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(2-piperidin-1-ylethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine | 1142939-30-7 | C27H29N5O2 |
| —— | (+/-)-{[7-(2,3-difluorophenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-92-6 | C17H17F2NO2 |
| —— | (Z)-7-(3-fluorobenzylidene)-5-methoxy-5,7-dihydrofuro[3,4-b]pyridine | 1273420-46-4 | C15H12FNO2 |
| —— | 1-methyl-(3ar,8bc)-1,3,3a,8b-tetrahydro-benzo[4,5]furo[3,2-c]isoxazole | 28082-12-4 | C10H11NO2 |
| —— | ((2R,3S)-3-Butyl-5-propoxy-2,3-dihydro-benzofuran-2-yl)-acetic acid methyl ester | 126666-09-9 | C18H26O4 |
| —— | 2-(3-fluoro-phenyl)-cyclopropanecarboxylic acid [1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-amide | 701913-66-8 | C20H20FNO2 |
| —— | methyl [(3S)-6-{[3-(3,4-dihydro-2H-pyran-6-yl)-2,4-dimethylbenzyl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetate | 1258398-40-1 | C25H29NO4 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(2,3-dihydro-1-benzofuran-5-ylmethyl)thio]-1,3,4-oxadiazole | 1005200-34-9 | C19H16N2O3S |
| —— | 2-(3-bromopropyl)-5,6-cyclopenteno-2H-1,4-benzoxazin-3(4H)-one | 139515-92-7 | C14H16BrNO2 |
| —— | 3-(4-(2,3-dihydro-1-benzofuran-5-yl)phenyl)-2,2,5-trimethyl-N-(1,3,4-thiadiazol-2-yl)hexanamide | 1025474-27-4 | C25H29N3O2S |
| —— | 6-(2-isopropyl-allyloxy)-4-methoxy-3-methyl-2,3-dihydro-benzofuran | 68706-75-2 | C16H22O3 |
| —— | (+/-)-N-methyl-1-[7-(3,4-difluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine | 852125-14-5 | C17H14F5NO |
| —— | 4-benzylidene-2,6-di-<i>tert</i>-butyl-8,9b-dimethyl-4a,9b-dihydro-4<i>H</i>-dibenzofuran-3-one | 66737-79-9 | C29H34O2 |
| —— | 7-Methoxy-4-[1-oxo-2-(4-pyridyl)ethyl]-spiro[2,3-dihydrobenzofuran-2,1'-cyclohexane] hydrochloride | 185401-28-9 | C21H23NO3*ClH |
| —— | 2,11,18,27-Tetraoxapentacyclo[26.4.0.04,9.012,17.020,25]dotriaconta-1(32),4(9),12,14,16,20(25),28,30-octaene-6,6,7,7,22,22,23,23-octacarbonitrile | 1386375-44-5 | C36H24N8O4 |
| —— | spiro<benzofuran-2(3H),1'-4'-methylcyclohex-2'ene>-3-carboxylic acid | 89955-30-6 | C15H16O3 |
| —— | dimethyl 2-((4R)-3,4-dihydro-2-hydroxy-6-methoxy-2H-chromen-4-yl)malonate | 1346013-13-5 | C15H18O7 |
| —— | 2-(2'hydroxy-2',3'-dihydrobenzofuran-3'yl)phenol | 124483-20-1 | C14H12O3 |
| —— | (+/-)-{[7-(2,4-difluorophenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-95-9 | C17H17F2NO2 |
| —— | 3,4-diiodo-7-methoxy-5-phenyl-2,5-dihydrobenzo[b]oxepine | 1266366-31-7 | C17H14I2O2 |
| —— | (6-hydroxy-5-methyl-2,3-dihydro-benzofuran-3-yl)-acetic acid methyl ester | 1380390-27-1 | C12H14O4 |
| —— | (4bS,4cR,9aS,9bR)-3,6-Dichloro-4b,4c-dihydro-9,10-dioxa-cyclobuta[1,2-a;4,3-a']diindene-9a,9b-dicarboxylic acid monoethyl ester | 67194-02-9 | C20H14Cl2O6 |
| —— | 1243185-41-2 | C2HF3O2*C24H17NO2 | |
| —— | 61245-36-1 | C19H24ClNO2S2 | |
| —— | 2-Methyl-2,3-dihydro-1-benzofuran-6-carbaldehyde | 1509521-67-8 | C10H10O2 |
| —— | 4-bromo-2,2-dimethyl-3H-1-benzofuran-7-ol | 1259401-35-8 | C10H11BrO2 |
| —— | 3-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)propanoic acid | 926268-51-1 | C13H16O4 |