香豆素
香豆素
基本信息
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。
相关化合物
| 中文名称 | 英文名称 | CAS号 | 化学式 |
|---|---|---|---|
| —— | 2-(6-methoxy-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole | 89197-46-6 | C12H14N2O2 |
| —— | 2,3-dihydro-2-carboxy-6-methoxybenzofuran | 41910-91-2 | C10H10O4 |
| —— | ethyl 2,3-dihydro-6-methoxybenzofuran-2-carboxylate | 90246-76-7 | C12H14O4 |
| —— | 2-((4-benzyl-1H-1,2,3-triazol-1-yl)methyl)-2,3-dihydrobenzofuran-5-carbonitrile | 1212056-66-0 | C19H16N4O |
| —— | 2-(azidomethyl)-2,3-dihydrobenzofuran-5-carbonitrile | 1212056-52-4 | C10H8N4O |
| —— | 4-benzyl-1-[(4,7-dimethyl-2,3-dihydrobenzofuran-2-yl)methyl]-1H-1,2,3-triazole | 1212056-59-1 | C20H21N3O |
| —— | 2-(azidomethyl)-4,7-dimethyl-2,3-dihydrobenzofuran | 1212056-51-3 | C11H13N3O |
| —— | 2-(azidomethyl)-2,3-dihydrobenzofuran-5-carbaldehyde | 1212056-50-2 | C10H9N3O2 |
| —— | 2-[(4-benzyl-1H-1,2,3-triazol-1-yl)methyl]-2,3-dihydrobenzofuran-5-carbaldehyde | 1212056-57-9 | C19H17N3O2 |
| —— | 5-(5-coumaranyl)-2-(4-pyridyl)oxazole | 151426-98-1 | C16H12N2O2 |
| —— | 2,3-dihydro-7-methoxy-a,2,2-trimethyl-5-benzofuranethanamine | 521068-51-9 | C14H21NO2 |
| —— | 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine | 274907-75-4 | C22H29NO |
| —— | 2-((Z)-1-Methyl-propenyl)-2,3-dihydro-benzofuran | 117436-91-6 | C12H14O |
| —— | (2,2-dimethyl-2,3-dihydrobenzofuran-3-yl)methanol | 1421681-69-7 | C11H14O2 |
| —— | 3-(dimethoxymethyl)-2,2-dimethyl-2,3-dihydrobenzofuran | 1421681-70-0 | C13H18O3 |
| —— | 2-(2,3-dihydrobenzofuran-7-yloxy)ethyl chloride | 245762-34-9 | C10H11ClO2 |
| —— | 2-(7-Methoxy-2,3-dihydro-1-benzofuran-3-yl)ethanamine | 372516-20-6 | C11H15NO2 |
| —— | N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-trifluoro-N-[2-(7-methoxy-2,3-dihydrobenzofuran-3-yl)-ethyl]-methanesulfonamide | 372516-03-5 | C18H22F3NO6S |
| —— | 2,3,4,t-4a-tetrahydrodibenzofuran-r-3,c-4-dicarboxylic anhydride | 138552-66-6 | C14H10O4 |
| —— | 2,3,4,4a-tetrahydrodibenzofuran-3,3,4,4-tetracarbonitrile | 138552-63-3 | C16H8N4O |
| —— | (+/-)-{[7-(2,5-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852121-80-3 | C15H12Cl2FNO |
| —— | (+/-)-{[7-(2,5-dichlorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-92-0 | C16H12Cl2F3NO |
| —— | 7-amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran | 164915-30-4 | C10H12ClNO |
| —— | ethyl 2-bromo-3-<4-<N-<(3R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3-ylmethyl>-(2S)-pyrrolidin-2-ylmethoxy>phenyl>propanoate | 199109-36-9 | C37H46BrNO5 |
| —— | 5-<4-<N-<(3R/S)-2,3-dihydro-5-benzyloxy-2,2,4,6,7-pentamethylbenzofuran-3-ylmethyl>-(2S)-pyrrolidin-2-ylmethoxy>phenylmethyl>-2-imino-4-thiazolidinone | 224954-16-9 | C36H43N3O4S |
| —— | 2-<N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3ylmethyl)-N-methylamino>ethanol | 187340-94-9 | C24H33NO3 |
| —— | 5-[[4-[(2,2,4,6,7-pentamethyl-5-phenylmethoxy-3H-1-benzofuran-3-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione | 224954-07-8 | C31H33NO5S |
| —— | 5-<4-<2-<N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3-ylmethyl)-N-methylamino>ethoxy>phenylmethyl>thiazolidine-2,4-dione | 187340-70-1 | C34H40N2O5S |
| —— | 4-<N-<(3R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl>-(3R)-piperidinyloxy>benzaldehyde | 224954-08-9 | C33H39NO4 |
| —— | 5-[[4-[[(2S)-1-[(2,2,4,6,7-pentamethyl-5-phenylmethoxy-3H-1-benzofuran-3-yl)methyl]pyrrolidin-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione | 199108-28-6 | C36H42N2O5S |
| —— | 4-[2-[N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]benzaldehyde | 187341-22-6 | C31H37NO4 |
| —— | 4-(5-benzyloxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethoxy)benzaldehyde | 224953-99-5 | C28H30O4 |
| —— | N-<(3R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl>-(3R)-chloropiperidine | 199108-89-9 | C26H34ClNO2 |
| —— | 2-<N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3-ylmethyl)-N-methylamino>ethyl chloride | 187341-07-7 | C24H32ClNO2 |
| —— | 4-<N-<(3R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl>-(2S)-pyrrolidin-2-ylmethoxy>benzaldehyde | 199109-07-4 | C33H39NO4 |
| —— | (S)-5-bromo-3,6-dimethyl-2,3-dihydrobenzofurane | 1242447-13-7 | C10H11BrO |
| —— | 2,3-dihydro-3-methylenebenzofuran-2-yl acetate | 1370000-01-3 | C11H10O3 |
| —— | 3-(4-isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine]-5-amine | 274907-74-3 | C25H34N2O |
| —— | 3-(4-isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H),4'-piperidine] | 274907-73-2 | C25H33NO |
| —— | 3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4'-piperidine] hydrochloride | 274907-72-1 | C24H31NO*ClH |
| —— | 2-iodomethyl-7-methoxy-2,3-dihydrobenzofuran | 135634-26-3 | C10H11IO2 |
| —— | 3-allyl-1-((4,6-dimethyl-2,3-dihydrobenzofuran-2-yl)methyl)-1H-imidazol-3-ium bromide | 1311989-65-7 | Br*C17H21N2O |
| —— | 3-(2-bromobenzyl)-1-((4,6-dimethyl-2,3-dihydrobenzofuran-2-yl)methyl)-1H-imidazol-3-ium bromide | 1311989-63-5 | Br*C21H22BrN2O |
| —— | 3-benzyl-1-((4,6-dimethyl-2,3-dihydrobenzofuran-2-yl)methyl)-1H-imidazol-3-ium bromide | 1311989-67-9 | Br*C21H23N2O |
| —— | (2,3-dihydro-4,6-dimethylbenzofuran-2-yl)methanamine | 29027-44-9 | C11H15NO |
| —— | 4,6-dimethyl-3-phenyl-3-p-tolylbenzofuran-2(3H)-one | 1373335-04-6 | C23H20O2 |
| —— | 2,3-dihydro-2,3-dihydroxy-4,7-dimethoxy-2-methylbenzo<b>furan | 145103-55-5 | C11H14O5 |
| —— | (E)-3-(2-methoxyvinyl)-2,3-dihydrobenzofuran | 1380570-59-1 | C11H12O2 |
| —— | 2-methylene-3-phenyl-2,3-dihydrobenzofuran-3-ol | 1060728-90-6 | C15H12O2 |
| —— | 5-methyl-7-nitro-2,3-dihydrobenzofuran | 1609171-13-2 | C9H9NO3 |
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