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 |
|---|---|---|---|
| —— | (R)-2-[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydrobenzofuran-2-yl]ethaneamine hydrochloride | 885517-76-0 | C16H14Cl2FNO*ClH |
| —— | 6-methoxy-3-(2,4,6-trimethoxy-benzyl)-2,3-dihydro-benzofuran | 102162-77-6 | C19H22O5 |
| —— | 4-Methyl-2,3-dihydro-1-benzofuran-5-amine | 1368293-73-5 | C9H11NO |
| —— | 3-Chlor-4b,8,9b-trimethyl-4b,9b-dihydro-benzofuro<3.2-b>benzofuran | 4200-13-9 | C17H15ClO2 |
| —— | (S)-3-[Benzyl-((R)-1-phenyl-ethyl)-amino]-3-(2,3-dihydro-benzofuran-5-yl)-propionic acid ethyl ester | 299912-79-1 | C28H31NO3 |
| —— | 4-(2,3-Dihydro-1-benzofuran-5-yl)pyrrolidin-2-one | 1367023-57-1 | C12H13NO2 |
| —— | 2-bromomethyl-4,7-di-<i>tert</i>-butyl-2,3-dihydro-benzofuran | 6883-86-9 | C17H25BrO |
| —— | (3RS,3aSR,8aSR)-2,3,3a,8a-Tetrahydro-3-hydroxy-4,6-dimethoxy-2,2-dimethylfuro<2,3-b>benzofuran | 83768-71-2 | C14H18O5 |
| —— | 1-(5-bromo-4-methoxy-3,3-dimethyl-2H-1-benzofuran-7-yl)pyrimidine-2,4-dione | 1309356-94-2 | C15H15BrN2O4 |
| —— | 5-(1-phenylethylidene)-2,3-dihydro-1-benzofuran-1-ium | 81390-57-0 | C16H15O |
| —— | ((6S,11S,12R)-8,9-dimethoxy-11,12-dihydro-6H-6,12-methanodibenzo[b,f]oxocin-11-yl)(furan-2-yl)methanone | 1447951-72-5 | C23H20O5 |
| —— | N-({1-[(3,3-dimethyl-2,3-dihydro-1,4-benzodioxin-5-yl)methyl]piperidin-4-yl}methyl)-2-(1H-imidazol-1-yl)acetamide | 1048960-41-3 | C22H30N4O3 |
| —— | 3-Amino-spiro[benzofuran-2(3H),1'-cycloheptane]hydrochloride | 106790-16-3 | C14H19NO*ClH |
| —— | 3-[2-(2,3-dihydro-benzofuran-5-yl)-ethyl]-6-methyl-1H-indazol-4-ol | 835885-27-3 | C18H18N2O2 |
| —— | 8-ethyl 8b-methyl 3a,5-di-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-8,8b-dicarboxylate | 1397495-93-0 | C16H18O7 |
| —— | 5-chloro-3,3-dimethyl-2,3-dihydrobenzofuran-4-ol | 1597548-43-0 | C10H11ClO2 |
| —— | 2,3,6,7-tetrahydro-benzo[1,2-b;4,5-b']difuran-4-carboxylic acid {(1R,3S,4S)-2-[5-(3-chloro-phenyl)-2-methyl-thiazole-4-carbonyl]-2-aza-bicyclo[2.2.1]hept-3-ylmethyl}-amide | 1181571-70-9 | C29H28ClN3O4S |
| —— | 2-methoxy-5-methyl-3-phenyl-2,3-dihydrobenzofuran | 173605-12-4 | C16H16O2 |
| —— | 3-[2,3-dihydro-2,2,4,6-tetramethyl-5-dimethylaminobenzo[b]furan-7-yl]propanal | 149245-54-5 | C17H25NO2 |
| —— | 4-benzyloxy-2-difluoromethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide | 955883-07-5 | C21H19F2N3O3 |
| —— | 4-Bromo-2a,7b-dihydro-2a,7b-dimethyl-1,2-dioxeto<3,4-b>benzofuran | 128753-89-9 | C10H9BrO3 |
| —— | 9-Methyl-4,11-dihydro-5H-1,6-dioxa-benzo[a]cyclopenta[d]cyclooctene-11-thiol | 141620-78-2 | C14H14O2S |
| —— | 2-ethylhexyl 3-[(5-chloro-2,3-dihydro-1-benzofuran-6-yl)thio]propanoate | 1156468-71-1 | C19H27ClO3S |
| —— | 3-benzyl-2-(2,2-dimethyl-2,3-dihydro-benzofuran-7-yl)-thiazolidin-4-one | 1255932-34-3 | C20H21NO2S |
| —— | 4-(1-(3-bromophenyl)vinyl)-5-methyl-2,3-dihydrobenzofuran | 1582778-66-2 | C17H15BrO |
| —— | N-({1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]piperidin-4-yl}methyl)-2-(2-nitro-1H-imidazol-1-yl)-acetamide trifluoroacetate | 1048960-33-3 | C2HF3O2*C22H29N5O4 |
| —— | (-)-2-isopropyl-2,3-dihydrobenzofuran-5-carbaldehyde | 74695-09-3 | C12H14O2 |
| —— | (7-Methoxy-3,3-dimethyl-2,3-dihydro-benzofuran-4-yl)-methanol | 107345-59-5 | C12H16O3 |
| —— | 2-bromo-N-(2,3-dihydro-benzofuran-6-yl)-N-[2-(4-fluoro-phenyl)-ethyl]-acetamide | 1111735-92-2 | C18H17BrFNO2 |
| —— | d2-2-(2,3-dihydro-benzofuran-yl)-ethanol | 1095599-83-9 | C10H12O2 |
| —— | N-hydroxy-N-[2-(2,3-dihydro-2-ethylbenzo[b]furan-5-yl)-ethyl] urea | 138560-98-2 | C13H18N2O3 |
| —— | (4S,6aS,11bR)-11-(1,3-dioxolan-2-ylmethyl)-8-methoxy-3-methyl-2,3,4,5-tetra-hydro-1H-4,11b-methano[1]benzofuro[3,2-d]azocin-6-one | 1315614-03-9 | C20H25NO5 |
| —— | 7-chloro-2,3-dihydro-5-nitro-6-(β-nitrovinyl)benzofuran-2-carboxylic acid methyl ester | 88062-24-2 | C12H9ClN2O7 |
| —— | N-ethyl-2,3-dihydro-6-methoxy-2-methyl-4-benzofuranamine | 68787-81-5 | C12H17NO2 |
| —— | (3aR,4R,5R,6aS)-4-((E)-(R)-3-(S)-2,3-Dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one | 66673-58-3 | C18H20O5 |
| —— | 3-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)-5-cyclopentyl-isoxazole | 1333118-48-1 | C22H29NO3 |
| —— | (2R,2'R,6aR,6a'R,12aS,12a'S)-O,O'-(1,4-phenylenebis(methylene))bis(8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydro(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one oxime) | 1076247-19-2 | C54H52N2O12 |
| —— | 7-(3,3-dimethylbut-1-ynyl)-2-ethyl-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-5-ol | 1432504-80-7 | C23H26O3 |
| —— | 1-[4-(2,3-dihydro-benzofuran-6-yl)-cyclohex-3-enyl]-azetidin-3-ylamine | 1252615-66-9 | C17H22N2O |
| —— | 6-methyl-3-<i>p</i>-tolyl-3<i>H</i>-benzofuran-2-one | 32305-01-4 | C16H14O2 |
| —— | 2-hydroxymethyl-4-isopropoxy-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide | 955882-98-1 | C17H21N3O4 |
| —— | 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-(methylsulfamoylcarbamoyl) N-methylcarbamate | 129072-78-2 | C14H19N3O6S |
| —— | (E)-2-(4-bromobenzylidene)-2,3-dihydrobenzofuran-3-ol | 1147869-71-3 | C15H11BrO2 |
| —— | 7-Methoxy-3,3-dimethyl-2,3-dihydro-benzofuran-4-carbonitrile | 107345-60-8 | C12H13NO2 |
| —— | (4-methoxy-phenyl)-(5,6,7,8-tetrachloro-3-thiophen-2-yl-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol | 73860-66-9 | C20H14Cl4O4S |
| —— | 2-(iodomethyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran | 1610696-23-5 | C10H8F3IO |
| —— | spiro[3H-3-bromobenzofuran-2,3'-(1'-acetyl-6'-bromo-2',5'-piperzinedione)] | 194487-84-8 | C13H10Br2N2O4 |
| —— | Acetic acid (R)-2-(2,3-dihydro-benzofuran-2-yl)-allyl ester | 77397-52-5 | C13H14O3 |
| —— | (R)-2-((R)-5-Ethyl-2,3-dihydro-benzofuran-2-yl)-propan-1-ol | 87503-40-0 | C13H18O2 |
| —— | 1202023-71-9 | C15H20O |