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 |
|---|---|---|---|
| —— | 2,5,6-triphenyl-5,6-dihydro-2H-[1,4]dioxino[2',3':3,4]naphtho[1,2-d][1,2,3]triazole | 120267-32-5 | C30H21N3O2 |
| —— | dimethyl 6H-benzo[c]chromene-4,9-dicarboxylate | 1332637-11-2 | C17H14O5 |
| —— | (S)-2-(7-chloro-2,3-dihydrofuro[2,3-c]pyridin-2-yl)propan-2-ol | 1269598-99-3 | C10H12ClNO2 |
| —— | 2-[3-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-5-methyl-1,3,4-oxadiazole | 1005202-61-8 | C18H16N2O3 |
| —— | (1S,1aR,6aR)-1-Methyl-1a,6a-dihydro-1H-6-oxa-cyclopropa[a]indene | 117607-52-0 | C10H10O |
| —— | (S,E)-4-(6-methoxychroman-2-yl)-2-methylbut-3-en-2-ol | 1177405-77-4 | C15H20O3 |
| —— | 1016896-61-9 | C29H34BrNO8 | |
| —— | 4-hydroxy-2-isopropenyl-6-methoxy-2,3-dihydrobenzofuran-5-carbaldehyde | 1058196-42-1 | C13H14O4 |
| —— | methyl 4-(4-(7-fluoro-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)-2,3-dihydrobenzofuran-5-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butanoate | 1346529-04-1 | C30H39FN4O5S |
| —— | 2H-1-Benzopyran-4-ol, 3,4-dihydro-8-methoxy-3-(1-methylethenyl)-, cis- | 139579-44-5 | C13H16O3 |
| —— | 2-Ethynyl-2,5-dimethyl-3-phenyl-2,3-dihydro-benzofuran-3-ol | 130155-81-6 | C18H16O2 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[[(3-fluorophenyl)sulfonyl]methyl]-1,3,4-oxadiazole | 1005200-98-5 | C17H13FN2O4S |
| —— | 2-phenyl-cyclopropanecarboxylic acid [1-(2,3-dihydro-benzofuran-5-yl)-ethyl]-amide | 701913-69-1 | C20H21NO2 |
| —— | (+/-)-4-[2-(3,5-Dichloro-4-pyridyl)-1-hydroxyethyl]-7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran | 185406-43-3 | C18H19Cl2NO3 |
| —— | 1,10-dimethyl-5,8-diphenyl-5,6,7,8-tetrahydro-1<i>H</i>-5,8-epiazano-benzo[<i>f</i>]indole-6,7-dicarboxylic acid anhydride | 66572-19-8 | C28H22N2O3 |
| —— | 5,7-Difluoro-2,3-dihydro-1-benzofuran-3-amine | 939757-44-5 | C8H7F2NO |
| —— | 5-bromo-3,3-dimethyl-7-hexyl-2,3-dihydro-benzofuran | 623176-35-2 | C16H23BrO |
| —— | Ta{OC6H2-4-CH3-(CH3)3CC(CH3)2CH2}2(C6H4-3-CH3) | 110433-68-6 | C37H51O2Ta |
| —— | phenyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7-benzofuranyl]oxy]carbonyl]amino]thio]-2-methylpropiothioimidate | 93960-85-1 | C22H26N2O3S2 |
| —— | 5-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine | 1142939-22-7 | C26H27N5O2 |
| —— | 2,2-dimethyl-7-phenyl-3H-1-benzofuran | 1286763-02-7 | C16H16O |
| —— | 4-(2,2-dimethyl-2,3-dihydrobenzo[2,3-b]furan-7-yloxy)butyl acetate | 884604-53-9 | C16H22O4 |
| —— | diethyl 3-hydroxy-5-methylbenzofuran-2,2(3H)-dicarboxylate | 1400892-29-6 | C15H18O6 |
| —— | 2,3-Dihydro-3,3-dimethyl-5-trifluoromethansulfonyloxybenzofurane | 131394-46-2 | C11H11F3O4S |
| —— | methyl 3-[[4-[4,7-difluoro-2-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-5-yl]-3,6-dihydro-2H-pyridin-1-yl]sulfonyl]propanoate | 1346529-50-7 | C29H36F2N4O5S |
| —— | 1-(1-((2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl)azetidin-3-yl)-4-(1,3-thiazol-2-ylcarbonyl)piperazine | 1252768-58-3 | C22H26N4O3S |
| —— | 1141759-35-4 | C16H26O3S | |
| —— | 5-chloro-2,3-dihydrobenzofuran-7-carbaldehyde | 82060-93-3 | C9H7ClO2 |
| —— | (4aS,7aR,12bS)-4a-Methyl-2,3,4,4a,5,6-hexahydro-1H-8-oxa-benzo[d]fluoren-7-one | 59262-30-5 | C17H20O2 |
| —— | 5-bromo-3-(4-isopropylphenyl)-2,3-dihydro-1-benzofuran | 820257-28-1 | C17H17BrO |
| —— | 3-deuterio-3-methyl-2H-1-benzofuran | 58401-12-0 | C9H10O |
| —— | (4aS,9bS)-2-Dimethylaminomethyl-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-3-one | 68788-86-3 | C17H21NO2 |
| —— | [(3S)-6-{[(3S)-7-{2,6-dimethyl-4-[(3-methyloxetan-3-yl)methoxy]phenyl}-2,3-dihydro-1-benzofuran-3-yl]amino}-2,3-dihydro-1-benzofuran-3-yl]acetic acid | 1258396-46-1 | C31H33NO6 |
| —— | (2,3-dihydro-benzofuran-2-ylmethyl)-pyridin-2-yl-amine | 29040-20-8 | C14H14N2O |
| —— | (+/-)-trans-7-Dimethylamino-3-hydroxy-2-methyl-2,3-dihydro-benzofuran | 26819-64-7 | C11H15NO2 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(3-fluorophenoxy)methyl]-1,3,4-oxadiazole | 1005200-96-3 | C17H13FN2O3 |
| —— | 5-Hydroxymethyl-7-methyl-8-((1E,3E)-4-phenyl-buta-1,3-dienyl)-4H-[1,3]dioxino[4,5-c]pyridin-7-ium; iodide | 105551-14-2 | C19H20NO3*I |
| —— | (+/-)-{[7-(2,5-dichlorophenyl)-5-methoxy-2,3-dihydro-1-benzofuran-2-yl]methyl}amine | 852123-37-6 | C16H15Cl2NO2 |
| —— | 7-benzyl-3,3-dimethyl-5-(3-hydroxy-1-methyl-prop-(1Z)-enyl)-2,3-dihydro-benzofuran | 623176-19-2 | C21H24O2 |
| —— | 723311-10-2 | C30H39ClFN3O2 | |
| —— | [Cu([D6]calix[6]tmpa)](OTf) | 1195852-99-3 | CF3O3S*C90H108CuN4O6 |
| —— | (R)-1-((S)-4-Hydroxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-2-methyl-propane-1,2-diol | 70270-44-9 | C13H18O5 |
| —— | 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[(4-methylbenzyl)thio]-1,3,4-oxadiazole | 1005200-28-1 | C18H16N2O2S |
| —— | (2,2-dimethyl-3H-1-benzofuran-7-yl) N,N-dimethylsulfamate | 1286762-99-9 | C12H17NO4S |
| —— | 2-[(3,4-dichlorobenzyl)thio]-5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazole | 1005200-57-6 | C17H12Cl2N2O2S |
| —— | (+/-)-1-[7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine | 852126-60-4 | C15H13Cl2NO |
| —— | 8-methoxy-3,4,4a,10b-tetrahydro-5<i>H</i>-pyrano[3,2-<i>c</i>]chromen-2-one | 66832-78-8 | C13H14O4 |
| —— | (S)-2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (2,3-dihydro-benzofuran-4-yl)-amide | 1232688-15-1 | C20H17FN2O3 |
| —— | 2-(5-Chloro-2,3-dihydro-1-benzofuran-7-yl)acetic acid | 1461715-07-0 | C10H9ClO3 |
| —— | (E)-1-Phenyl-3-(5,6,7,8-tetrachloro-3a,9a-dihydro-benzo[b]furo[2,3-e][1,4]dioxin-2-yl)-prop-2-en-1-ol | 73860-56-7 | C19H12Cl4O4 |