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 |
|---|---|---|---|
| —— | (1S,4aS,9aS)-2-(6-nitro-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-2-yl)-ethylcarboxylate | 1058712-86-9 | C17H20N2O5 |
| —— | 1-ethyl-3-[2-(5-methoxy-2,3-dihydro-benzofuran-3-yl)-ethyl]-urea | 1148035-94-2 | C14H20N2O3 |
| —— | 5-Methoxy-6-nitro-2-octyl-2,3-dihydrobenzofuran | 172083-60-2 | C17H25NO4 |
| —— | 9-Oxo-2,3,5-trimethyl-7,8,9,10-tetrahydro-6H-benzofuro<7,6-b>-azepin | 40728-44-7 | C15H17NO2 |
| —— | N-[1-(2,3-dihydro-5-benzofuranyl)ethyl]-2-(3-methoxyphenyl)-4-(trifluoromethyl)-5-thiazolecarboxamide | 725248-41-9 | C22H19F3N2O3S |
| —— | Benzofuran, 2-ethyl-2,3-dihydro-3-methyl-, cis- | 13629-70-4 | C11H14O |
| —— | 1-(8,9b-dimethyl-3,4,4a,9b-tetrahydro-dibenzofuran-3-yl)-4-methyl-piperazine | 68788-78-3 | C19H26N2O |
| —— | 7-[4-(2-ethoxyethoxy)phenyl]-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-carbaldehyde | 865138-31-4 | C21H24O4 |
| —— | 3-(4-isopropylphenyl)-2,2,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-amine hydrochloride | 820257-77-0 | C21H27NO*ClH |
| —— | 5,7-dimethoxy-2,4-dimethyl-2<i>H</i>-chromen-2-ol | 853926-76-8 | C13H16O4 |
| —— | (S)-2,3-dihydro-benzofuran-4-carboxylic acid {1-[5-(2-fluoro-phenyl)-2-phenyl-thiazole-4-carbonyl]-piperidin-2-ylmethyl}-amide | 1137129-36-2 | C31H28FN3O3S |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-N,N-diethyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488125-90-2 | C21H24Cl2N2O |
| —— | 2-Chloromethyl-5,7-bis-(1-ethoxy-ethoxy)-2,3-dihydro-benzofuran | 138224-01-8 | C17H25ClO5 |
| —— | [(3S)-6-{[(3S)-7-{2,6-dimethyl-4-[2-(2-oxopyrrolidin-1-yl)ethoxy]phenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-36-9 | C32H34N2O6 |
| —— | 2-(5-chloro-2,3-dihydrobenzofuran-3-yl)acetic acid | 1221498-00-5 | C10H9ClO3 |
| —— | 4-(6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-(5-(2-chlorophenyl))-thiazol-2-amine | 1189811-04-8 | C20H14ClN3OS2 |
| —— | N-[2-(5-methoxy-2,3-dihydro-benzofuran-3-yl)-ethyl]-propionamide | 1148035-90-8 | C14H19NO3 |
| —— | 1-cyclobutyl-5'-(piperidin-1-yl)-3'H-spiro[azepane-4,2'-benzofuran] | 1258430-23-7 | C22H32N2O |
| —— | (+/-)-{[7-(4-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-46-4 | C16H16ClNO |
| —— | 2-fluoro-N-((3S)-1-(7-fluoro-2-methyl-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-yl)propanamide | 1258851-34-1 | C16H20F2N2O2 |
| —— | 2,4-Dimethyl-4,5-dihydro-5-carbomethoxy-2,5-epoxy-1,3-benzodioxepin | 60779-22-8 | C13H14O5 |
| —— | 4-Acetyl-4-phenyl-3-chromanon | 51737-02-1 | C17H14O3 |
| —— | 3-Hydroxy-5-methoxy-2-methyl-2,3-dihydrobenzo<b>furan | 60770-57-2 | C10H12O3 |
| —— | 9-Dimethoxymethyl-6-methoxy-2,2,9b-trimethyl-2,3,4a,9b-tetrahydro-1H-dibenzofuran-4-one | 55524-29-3 | C19H26O5 |
| —— | 6-fluoro-2,3-dihydro-2,2-dimethylbenzofuran | 960309-78-8 | C10H11FO |
| —— | 1187215-83-3 | C18H12Cl2F3NO2 | |
| —— | 2,2,6,7-tetramethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine | 820258-14-8 | C19H23NO |
| —— | 2,2,2-trifluoro-N-((3S)-1-(7-fluoro-2-methyl-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-yl)acetamide | 1258851-32-9 | C15H16F4N2O2 |
| —— | 2-selenocyanatomethyl-2,3-dihydro-benzofuran | 56917-84-1 | C10H9NOSe |
| —— | 8-(2-Chloro-benzyloxy)-2,2-dimethyl-3,4-dihydro-2H-benzo[f][1,4]oxazepine-5-thione | 144537-63-3 | C18H18ClNO2S |
| —— | (2R,3S,4R)-4-[[(cyanoimino)phenoxymethyl]amino]-6-methoxycarbonyl-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-1-benzopyran | 335382-56-4 | C23H25N3O7 |
| —— | 4,4-diphenyl-3,4-dihydrocoumarin | 971-84-6 | C21H16O2 |
| —— | (+/-)-{[7-(2,5-dimethylphenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-43-4 | C18H21NO2 |
| —— | (+/-)-{[7-(5-chloro-2-methoxyphenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-47-8 | C17H18ClNO3 |
| —— | 3-[2,2-Bis(ethylsulfanyl)ethyl]-5-methoxy-3-phenyl-1-benzofuran-2-one | 623163-92-8 | C21H24O3S2 |
| —— | 6-Chloro-5-iodo-2,3-dihydro-1-benzofuran-3-ol | 1154740-98-3 | C8H6ClIO2 |
| —— | [2-(5-methoxy-2,3-dihydro-benzofuran-3-yl)-ethyl]-cyclopropanecarboxamide | 1148035-92-0 | C15H19NO3 |
| —— | [(S)-1-(2,3-Dihydro-benzofuran-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester | 319478-44-9 | C17H24N2O3 |
| —— | (+/-)-{[7-(2,3-dimethylphenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-82-8 | C18H18F3NO |
| —— | 2,3-Dihydro-2,3-dihydroxy-5-methyl-benzo<b>furan-2,3-dicarbonsaeure-methylester | 342819-43-6 | C13H14O7 |
| —— | 66674-96-2 | C15H18O3 | |
| —— | 7-ethyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine | 820259-92-5 | C21H27NO |
| —— | <i>rac</i>-3,9β-dihydroxy-hasubanane-17-carboxylic acid 9-lactone | 59637-79-5 | C17H19NO3 |
| —— | N-((3S)-1-(7-fluoro-2-methy1-2,3-dihydrobenzofuran-4-yl)pyrrolidin-3-yl)propionamide | 1258851-33-0 | C16H21FN2O2 |
| —— | 5-(pyrrolidine-1-sulfonyl)-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 847949-03-5 | C14H17NO5S |
| —— | triisopropyl-[3-(7-bromo-2-methyl-2,3-dihydro-benzofuran-2-yl)-prop-1-ynyl]-silane | 1203447-38-4 | C21H31BrOSi |
| —— | 3-Hydroxy-5-methylthio-2,3-dihydro-benzo<b>furan | 60770-58-3 | C9H10O2S |
| —— | 1-tert-butyl 1-methyl 5-methoxy-1a,2-dihydrocyclopropa[c]chromene-1,1(7bH)-dicarboxylate | 1236004-45-7 | C18H22O6 |
| —— | 2,8-dimethyl-11a-methylpterocarpan | 14298-17-0 | C18H18O2 |
| —— | 4-Acetoxy-2a,7b-dihydro-2a,7b-dimethyl-1,2-dioxeto<3,4-b>benzofuran | 145723-24-6 | C12H12O5 |