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 |
|---|---|---|---|
| —— | trans-2,3-Dihydro-5-hydroxy-3-methylbenzofuran-2-carboxaldehyde N,N-dimethylhydrazone | 127280-15-3 | C12H16N2O2 |
| —— | (3R)-3-[2,2-bis(benzenesulfonyl)ethyl]-5-iodo-3-phenyl-1-benzofuran-2-one | 1374605-28-3 | C28H21IO6S2 |
| —— | annullatin B | 1370709-01-5 | C17H26O3 |
| —— | (12aS,6aR)-9-(4-fluorophenyl)-1-methoxy-7,7-dimethyl-7,12,12a,6a-tetrahydrochromano[4,3-b]quinoline | 946154-10-5 | C25H24FNO2 |
| —— | 10-Methoxy-1.2.3.4.10.11-hexahydro-diphenylenoxid | 97023-68-2 | C13H16O2 |
| —— | 7-[2-(3,5-Dichloro-4-pyridyl)-1-hydroxyethyl]-4-methoxy-spiro[2,3-dihydrobenzofuran-2,1'-cyclopentane] | 457934-39-3 | C20H21Cl2NO3 |
| —— | [(3S)-6-{[(3S)-7-(4-{2-[2-(dimethylamino)ethoxy]ethoxy}-2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-43-8 | C32H38N2O6 |
| —— | 2-(2,5-difluoro-phenyl)-cyclopropanecarboxylic acid [1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-amide | 701913-68-0 | C20H19F2NO2 |
| —— | 3-(2-Chloro-ethoxy)-N-((4R,9bS)-8,9b-dimethyl-3-oxo-1,2,3,4,4a,9b-hexahydro-dibenzofuran-4-yl)-propionamide | 61132-77-2 | C19H24ClNO4 |
| —— | 3-[[[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]thio]methyl]pyridine | 1005200-36-1 | C16H13N3O2S |
| —— | 4-(2-Butenyl)-2,3-dihydro-6,7-dimethoxy-5-hydroxy-3-pentylidenebenzofuran | 135482-13-2 | C19H26O4 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(3,5-dimethylbenzyl)thio]-1,3,4-oxadiazole | 1005200-51-0 | C19H18N2O2S |
| —— | (+/-)-1-[5-fluoro-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine | 852125-85-0 | C15H13F2NO |
| —— | 9-Methoxy-1,2,3,4,4a,9b-hexahydro-dibenzofuran | 27124-69-2 | C13H16O2 |
| —— | 5-bromo-3,3-dimethyl-7-(2,2-dimethyl-propyl)-2,3-dihydrobenzofuran | 623176-08-9 | C15H21BrO |
| —— | (S)-2,3-dihydro-benzofuran-4-carboxylic acid {1-[5-(2-fluoro-phenyl)-2-p-tolyl-thiazole-4-carbonyl]-piperidin-2-ylmethyl}-amide | 1137129-44-2 | C32H30FN3O3S |
| —— | 10-ethoxy-5H-imidazo[1,2-c][1,3]benzoxazine | 1402603-39-7 | C12H12N2O2 |
| —— | 2,2-dimethyl-5-amino-7-[2-(N-methyl-N-benzyl)-amino-ethoxy]-2,3-dihydro-benzofuran | 1089187-31-4 | C20H26N2O2 |
| —— | (5-phenyl-2,3-dihydro-benzofuran-3-yl)-methanol | 68224-05-5 | C15H14O2 |
| —— | 2,3-dihydro-2-oxo-3-phenyl-3-benzofurancarboxylic acid, n-butyl ester | 108139-64-6 | C19H18O4 |
| —— | 1224600-27-4 | C21H25ClN4O4 | |
| —— | 2-isopropenyl-6-(methoxymethyl)oxy-2,3-dihydrobenzofuran-5-carbaldehyde | 581096-51-7 | C14H16O4 |
| —— | 5-Methyl-3a-8a-dihydrofuro<2,3-b>benzofuran-2(3H)-one | 84097-11-0 | C11H10O3 |
| —— | 7-Methoxy-8b-methyl-1,2,3,8b-tetrahydro-benzo[b]cyclopenta[d]furan-3,3a-diol | 61076-59-3 | C13H16O4 |
| —— | 4-Chloro-N-((4R,9bS)-8,9b-dimethyl-3-oxo-1,2,3,4,4a,9b-hexahydro-dibenzofuran-4-yl)-butyramide | 58323-23-2 | C18H22ClNO3 |
| —— | 3,3-dimethyl-7-(3-oxo-heptyl)-2,3-dihydro-benzofuran-5-boronic acid | 623176-77-2 | C17H25BO4 |
| —— | (2S)-2-ethenyl-2,3-dihydro-1-benzofuran | 69119-19-3 | C10H10O |
| —— | ethyl 4-hydroxy-8-methoxy-4H-chromene-3-carboxylate | 1642135-70-3 | C13H14O5 |
| —— | (1R,9S,12R)-4,6-Dibromo-1,5,9,12-tetramethyl-8-oxa-tricyclo[7.2.1.0<sup>2,7</sup>]dodeca-2(7),3,5-triene | 139126-16-2 | C15H18Br2O |
| —— | 2-(N-Benzylaminomethylen)-3(2H)-benzofuranthion | 78096-44-3 | C16H13NOS |
| —— | (1R,4aR,9aS)-6-nitro-2-(2-phenethyl)-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridine | 1058712-76-7 | C22H24N2O3 |
| —— | 2-[(2,5-dichlorobenzyl)thio]-5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole | 1005200-56-5 | C17H12Cl2N2O2S |
| —— | (5-chloro-2,3-dihydrobenzofuran-7-yl)methanol | 1461713-52-9 | C9H9ClO2 |
| —— | [(3S)-6-{[3-(2,5-dimethylthiophen-3-yl)-2-methylbenzyl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258397-41-9 | C24H25NO3S |
| —— | 1'-(2-Methoxyphenyl)-4'-methylspiro(naphthalene-1(2H),2'(1'H)-naphtho<2,1-b>furan)-2-one | 146382-47-0 | C29H22O3 |
| —— | 8-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-2,8-diazaspiro[4.5]decane hydrochloric acid salt | 929302-15-8 | C19H28N2O*ClH |
| —— | 1,14-diphenyl-2,13,21-trioxapentacyclo[12.6.1.03,12.04,9.015,20]henicosa-3(12),4,6,8,10,15,17,19-octaene | 62423-38-5 | C30H20O3 |
| —— | 3-Hydroxy-6-methyl-2,3-dihydrobenzo<b>furan | 60770-54-9 | C9H10O2 |
| —— | 2-Chloro-N-((4R,9bS)-8,9b-dimethyl-3-oxo-1,2,3,4,4a,9b-hexahydro-dibenzofuran-4-yl)-acetamide | 58323-22-1 | C16H18ClNO3 |
| —— | (+/-)-{[7-(2,5-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852122-54-4 | C16H15Cl2NO |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(3-methoxybenzyl)thio]-1,3,4-oxadiazole | 1005200-23-6 | C18H16N2O3S |
| —— | (2S,3R)-3-Hydroxy-3-isopropyl-5-nitro-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester | 104862-30-8 | C13H15NO6 |
| —— | Ta{OC6H2-4-OCH3-(CH3)3CC(CH3)2CH2}2(C6H5) | 110433-67-5 | C36H49O4Ta |
| —— | (+/-)-{[7-(2,5-dichlorophenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}methylamine | 852124-97-1 | C17H17Cl2NO2 |
| —— | 5-hydroxy-6-methoxy-3-phenyl-3<i>H</i>-benzofuran-2-one | 66092-43-1 | C15H12O4 |
| —— | [(3S)-6-{[(3S)-7-{2,6-dimethyl-4-[3-(methylsulfanyl)propoxy]phenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-41-6 | C30H33NO5S |
| —— | 2aH-7-Oxa-cyclobuta[a]indene-7a-carboxylic acid methyl ester | 62250-84-4 | C12H10O3 |
| —— | 3,4,6,8-tetra-<i>tert</i>-butyl-1-propyl-3,3a-dihydro-benzo[4',5']furo[3',2':1,4]cyclobuta[1,2-<i>b</i>]pyrrol-2-one | 60434-63-1 | C31H47NO2 |
| —— | 7-benzyl-5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran | 623176-17-0 | C17H17BrO |
| —— | 3-(2,3-dihydro-benzofuran-5-ylmethyl)-2-(2-ethoxy-phenyl)-thiazolidin-4-one | 1255931-26-0 | C20H21NO3S |