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 |
|---|---|---|---|
| —— | (+/-)-{[7-(2,6-dimethylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852125-48-5 | C18H20FNO |
| —— | 3-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)-5-methylisoxazole-4-carboxylic acid | 1370419-02-5 | C15H15NO4 |
| —— | 4-(4-((5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methoxy)phenyl)butanoic acid | 1234843-51-6 | C21H23FO4 |
| —— | 5-Iodo-6-methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-4-ol | 128033-20-5 | C11H11IO4 |
| —— | 33230-90-9 | C17H16O4 | |
| —— | 2,4,4-trimethyl-4<i>H</i>-benzo[<i>e</i>][1,3]oxazine | 27412-24-4 | C11H13NO |
| —— | 2-(3,5-dichloropyridin-4-yl)-1-{9-methoxyspiro[2H-1,5-benzodioxepin-3(4H),5'-[1,3]dithiane]-6-yl}ethanone | 1051493-46-9 | C20H19Cl2NO4S2 |
| —— | 2,3-dihydro-2,2,4,6-tetramethyl-5-benzofuranoxyl | 286471-89-4 | C12H15O2 |
| —— | 2,3-Dihydro-N-<4-(1,1-dimethylethyl)phenylmethyl>-N-methyl-7-benzofurancarboxamid | 149530-56-3 | C21H25NO2 |
| —— | Methyl 5-cyano-2,3-dihydro-1-benzofuran-7-carboxylate | 1342299-82-4 | C11H9NO3 |
| —— | 5-acetoxy-4,6-di-tert-butyl-2,3-dihydro-2,2-dipenthylbenzofuran | 390393-99-4 | C28H46O3 |
| —— | 2,4,4-trimethyl-2,3-dihydro-1,3-benzoxazine | 117343-29-0 | C11H15NO |
| —— | Acetic acid 4,6-di-tert-butyl-2,2-diheptyl-2,3-dihydro-benzofuran-5-yl ester | 1026148-12-8 | C32H54O3 |
| —— | tert-butyl (3R,4R)-(3-methyl-chroman-4-ylmethyl)carbamate | 1301745-93-6 | C16H23NO3 |
| —— | 2-(2,3-Dihydro-1-benzofuran-5-yl)ethane-1-sulfonyl chloride | 1523391-72-1 | C10H11ClO3S |
| —— | 4-((2,3-dihydrobenzofuran-5-yl)methyl)-2-(4-fluorophenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile | 1207437-12-4 | C19H13FN4O3 |
| —— | tert-butyl 6,7-dichloro-5-<3-(2,2-dimethoxyethylamino)-3-methylthio-2-propenoyl>-2,3-dihydro-2-benzo<b>furancarboxylate | 126200-95-1 | C21H27Cl2NO6S |
| —— | 8-(2,4-dichlorophenyl)-6-[(1-ethylpropyl)thio]-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridine | 488125-15-1 | C22H25Cl2NOS |
| —— | 2,3-dihydro-3-(N,-methyl-N-propylaminomethyl)-5-hydroxybenzofuran | 118610-74-5 | C13H19NO2 |
| —— | 6-benzyl-6-methyl-6H-benzo[c]chromene | 1569315-69-0 | C21H18O |
| —— | (+/-)-(7-bromo-5-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanol | 852117-30-7 | C15H13BrO2 |
| —— | (5-chloro-3-methyl-2,3-dihydrobenzofuran-3-yl)methanol | 1333120-32-3 | C10H11ClO2 |
| —— | 2-(3,5-difluoro-4-((7-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-4-yl)methoxy)phenyl)cyclopropanecarboxylic acid | 1234842-65-9 | C21H19F3O4 |
| —— | 2-(2,5-Dimethyl-3-methylene-2,3-dihydro-benzofuran-2-yl)-4-methyl-phenol | 96014-28-7 | C18H18O2 |
| —— | 937254-97-2 | C17H17N3O4 | |
| —— | 2,4,4-trimethyl-chroman-2,7-dicarboxylic acid | 107682-95-1 | C14H16O5 |
| —— | 7-amino-6-hydroxy-6-trifluoromethyl-2,3,5,6-tetrahydro-1-oxa-3a-aza-phenalen-4-one | 619320-84-2 | C12H11F3N2O3 |
| —— | (2R,4aR,9aR)-5-bromo-2-(methoxymethoxy)-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-7-carbaldehyde | 1353178-25-2 | C19H25BrO4 |
| —— | 2,2-Dimethyl-propionic acid 4-(3-dimethylamino-propylamino)-5-nitro-2,3-dihydro-benzofuran-2-ylmethyl ester | 870771-80-5 | C19H29N3O5 |
| —— | (3aR,8bR)-8b-ethyl-1,3a,6-trimethyl-3H-cyclopenta[b][1]benzofuran | 138629-65-9 | C16H20O |
| —— | (2S,3R)-3-((R)-1-hydroxyethyl)-4,6-dimethoxy-2,3-dihydrobenzofuran-2-ol | 1356485-71-6 | C12H16O5 |
| —— | Acetic acid (1S,9S,11S,12S)-12-(2-methoxy-ethoxymethoxy)-1,4-dimethyl-8,13-dioxa-tricyclo[7.3.1.02,7]trideca-2,4,6-trien-11-yl ester | 112576-23-5 | C19H26O7 |
| —— | (R)-2-(4-(7-fluoro-5-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydrobenzofuran-2-yl)piperidin-1-yl)-5-propylpyrimidine | 1346529-70-1 | C25H31FN4O |
| —— | (4aS,9bR)-8-(2,4-dichlorophenyl)-N-propyl-N-cyclohexyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488126-00-7 | C26H32Cl2N2O |
| —— | N3-(2,3-dihydrobenzofuran-3-yl)-4H-1,2,4-triazole-3,5-diamine | 1518944-61-0 | C10H11N5O |
| —— | 2-chloro-4-(2,3-dihydrobenzofuran-5-yl)-6-fluoroaniline | 1346706-51-1 | C14H11ClFNO |
| —— | 1,2-trans-2,3a,8b-cis-2,3,3a,8b,tetrahydro-1H-5-(4-tetrahydropyranyloxybutyl)-1-(2-formylethenyl)-2-hydroxycyclopenta<b>benzofuran | 79020-80-7 | C23H30O5 |
| —— | rac-3,4-dihydro-6-hydroxy-3-(3-hydroxypropyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonitrile | 121175-52-8 | C17H23NO3 |
| —— | (2RS)-2,3-dihydrobenzofuran-7-carboxylic acid {1-[5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl]azetidin-2-ylmethyl}amide | 1007875-91-3 | C24H22FN3O3S |
| —— | 1116108-39-4 | C18H15F2N3O2*ClH | |
| —— | (+/-)-[7-(2-chlorophenyl)-6-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanol | 852118-05-9 | C15H12ClFO2 |
| —— | (+/-)-{[5-chloro-7-(2,3-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-62-0 | C16H14Cl3NO |
| —— | (Z)-4-(2-heptylidene-2,3-dihydrobenzofuran-3-yl)morpholine | 1159175-39-9 | C19H27NO2 |
| —— | 12-Phenyl-8-oxa-tricyclo[7.2.2.0<sup>2,7</sup>]trideca-2(7),3,5,12-tetraene-10,10,11,11-tetracarbonitrile | 57705-04-1 | C22H12N4O |
| —— | 2-(4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-yl)ethanol | 119384-85-9 | C12H16O4 |
| —— | (4aS,9bR)-8-(2,4,6-trichlorophenyl)-N-phenyl-1,2,3,4,4a,9b,-hexahydro[1]benzofuro[3,2-c]pyridin-6-amine | 488125-85-5 | C23H19Cl3N2O |
| —— | cis-2-chloro-3-deuterio-3-fluoro-2,3-dihydrobenzofuran | 86324-96-1 | C8H5Cl2FO |
| —— | 3,6-Benzofurandiamine, 2,3-dihydro-5,7-dimethyl-, (3R)- | 1272731-96-0 | C10H14N2O |
| —— | 4-Aethyl-3-oxo-chroman-4-carbonsaeure-aethylester | 92252-20-5 | C14H16O4 |
| —— | N-(2-Phenylsulfanylmethyl-2,3-dihydro-benzofuran-7-yl)-acetamide | 119118-15-9 | C17H17NO2S |