吡喃类化合物
吡喃类化合物是一种含有一个氧原子的六元杂环体系，主要分为α-吡喃和γ-吡喃两种异构体。尽管无取代基的α-吡喃和γ-吡喃尚未被发现，但其衍生物广泛存在于自然界中，尤其是植物中常见的α-及γ-吡喃酮。
这些化合物包括苯并吡喃（色烯）、色酮、香豆素、黄酮、异黄酮以及花青素等。从电子结构上看，吡喃类似苯系化合物，环中的氧原子具有极强的碱性，在成盐后被稳定下来。许多重要的天然产物如色素、糖类、抗生素及生物碱都含有吡喃或其盐形式的环系。例如，五碳糖或六碳糖形式的半缩醛结构被称为吡喃糖。
吡喃酮是通过将吡喃的次甲基部分氧化为羰基而形成的衍生物。α-吡喃酮为5-羟基-2,4-戊二烯酸的内酯，在酸碱催化下可以发生水解反应，也可以在催化氢化条件下转化为5-羟基戊酸内酯；此外，该化合物还能参与双烯合成反应。相比之下，γ-吡喃酮具有显著的芳香性特点，即使是一个不饱和酮，也不与苯肼形成腙，并且其羰基不易被还原。
一些重要药物如红霉素和双氢链霉素含有四氢吡喃环结构，而许多碳水化合物也具有四氢吡喃环。
| 中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
|---|---|---|---|---|
| 齐墩果酸 beta-D-吡喃葡萄糖基酯 | 28-O-β-D-glucopyranosyl oleanolate | 14162-53-9 | C36H58O8 |
|
| 黄芪异黄烷苷,7,2'-二羟基-3',4'-二甲氧基异黄烷 | methylnissolin-3-O-β-D-glucoside | 94367-42-7 | C23H26O10 |
|
| 黄檀素 | 6-Hydroxy-7-methoxy-4-phenyl-coumarin | 482-83-7 | C16H12O4 |
|
| 马索亚内酯 | (+/-)-massoialactone | 54814-64-1 | C10H16O2 |
|
| 香豆素314T | Coumarin 314T | 113869-06-0 | C22H27NO4 |
|
| 香豆素152 | coumarin-152 | 53518-14-2 | C12H10F3NO2 |
|
| 香豆素 30 | 7-(diethylamino)-3-(1-methyl-1H-benzimidazol-2-yl)-2Hchromen-2-one | 41044-12-6 | C21H21N3O2 |
|
| 香叶吡喃 | 2,4-Dimethyl-6-phenyl-3,6-dihydro-2<i>H</i>-pyran | 68039-40-7 | C13H16O |
|
| 辣椒素-Β-D-吡喃葡萄糖苷 | (E)-N-[[3-methoxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]-8-methylnon-6-enamide | 153409-16-6 | C24H37NO8 |
|
| 草质素-3-O-Β-D-吡喃葡萄糖-7-O-Α-L-鼠李糖苷 | herbacetin 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside | 909803-26-5 | C27H30O16 |
|
| 草枯醚 | p-nitrophenyl 2,4,6-trichlorophenyl ether | 1836-77-7 | C12H6Cl3NO3 |
|
| 茉莉吡喃 | 4-acetoxy-3-pentyl-tetrahydropyran | 18871-14-2 | C12H22O3 |
|
| 苯并二氢吡喃-4-胺盐酸盐 | 3,4-dihydro-2H-chromene-4-amine hydrochloride | 90609-63-5 | C9H11NO*ClH |
|
| 苯并二氢吡喃-3-羧酸 | chromane-3-carboxylic acid | 115822-57-6 | C10H10O3 |
|
| 苯基2-O-乙酰基-3,4,6-三-O-苯甲基-1-硫-β-D-半乳吡喃糖苷 | phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside | 183875-28-7 | C35H36O6S |
|
| 苯基1-硫代吡喃己糖苷 | (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol | 77481-62-0 | C12H16O5S |
|
| 苯基1-硫代-4-O-乙酰基-2,6-二-O-苯甲酰基-β-D-吡喃半乳糖苷 | 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside | 152488-28-3 | C28H26O8S |
|
| 苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 | (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol | 87508-17-6 | C19H20O5S |
|
| 苯基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-β-D-吡喃葡萄糖苷 | peracyl-N-Troc-phenyl-(S,O)-glucosamine | 187022-49-7 | C21H24Cl3NO9S |
|
| 苯基-2-脱氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-β-D-吡喃半乳糖苷 | Phenyl 2-Deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-galactopyranoside | 868230-98-2 | C15H18Cl3NO6S |
|
| 苯基 2,3,4,5-四-O-乙酰基-alpha-D-吡喃葡萄糖苷 | phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 3427-45-0 | C20H24O10 |
|
| 苄基2-脱氧-2-邻苯二甲酰亚胺基-3,4,6-三-O-乙酰基-beta-D-吡喃葡萄糖苷 | benzyl 3,4,6-tri-O-acetyl-2-phthalimido-2-deoxy-β-D-glucopyranoside | 80035-31-0 | C27H27NO10 |
|
| 苄基2-叠氮基-3,6-二-O-苄基-2-脱氧-Β-D-吡喃葡萄糖苷 | benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 342640-42-0 | C27H29N3O5 |
|
| 苄基-Β-L-吡喃阿拉伯糖苷 | benzyl β-L-arabinopyranoside | 7473-38-3 | C12H16O5 |
|
| 苄基 2-(乙酰氨基)-2-脱氧-6-O-(苯基甲基)-3-O-2-丙烯-1-基-alpha-D-吡喃葡萄糖苷 | benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside | 60920-82-3 | C25H31NO6 |
|
| 花椒毒醇 | 8-hydroxypsoralen | 2009-24-7 | C11H6O4 |
|
| 色酮-3-甲醛 | 3-Formylchromone | 17422-74-1 | C10H6O3 |
|
| 色酮-3-甲腈 | 4-oxo-4H-1-benzopyran-3-carbonitrile | 50743-17-4 | C10H5NO2 |
|
| 色酮-2-甲酸 | acide chromone carboxylique-2 | 4940-39-0 | C10H6O4 |
|
| 秦皮素 | 7,8-dihydroxy-6-methoxy-2H-1-benzopyran-2-one | 574-84-5 | C10H8O5 |
|
| 白蜡树素 | 6,7,8-trimethoxy-2H-chromen-2-one | 6035-49-0 | C12H12O5 |
|
| 甲基四-O-乙酰基-alpha-D-吡喃甘露糖苷 | methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 5019-24-9 | C15H22O10 |
|
| 甲基3,4,6-三-O-乙酰-2-脱氧-2-邻苯二甲酰亚氨基-1-硫代-β-D-吡喃葡萄糖苷 | methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 79528-48-6 | C21H23NO9S |
|
| 甲基2-乙酰氨基-2-脱氧-BETA-D-吡喃葡萄糖苷 | methyl N-acetyl-β-D-glucosaminide | 3946-01-8 | C9H17NO6 |
|
| 甲基1-硫代-beta-D-半乳吡喃糖苷酸甲酯三乙酸酯 | Methyl 3,4,5-triacetyloxy-6-methylsulfanyloxane-2-carboxylate | 29587-10-8 | C14H20O9S |
|
| 甲基-(四氢吡喃-4-甲基)胺 | N-methyl-1-(tetrahydro-2H-pyran-4-yl)methanamine | 439081-52-4 | C7H15NO |
|
| 甲基 1-C-[3-[[5-(4-氟苯基)-2-噻吩基]甲基]-4-甲基苯基]-D-吡喃葡萄糖苷 | methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methyl-phenyl)-D-glucopyranoside | 1030825-21-8 | C25H27FO6S |
|
| 瑞香素-7-甲醚 | 8-hydroxy-7-methoxy-2H-chromen-2-one | 19492-03-6 | C10H8O4 |
|
| 瑞香素 | daphnetin | 486-35-1 | C9H6O4 |
|
| 牡丹酚苷 | paeonoside | 20309-70-0 | C15H20O8 |
|
| 炔丙基α-D-吡喃甘露糖苷 | propargyl α-D-mannopyranoside | 854262-01-4 | C9H14O6 |
|
| 溴代四苄基-α-D-吡喃半乳糖 | tetra-O-benzyl-α-D-galactosyl bromide | 53081-30-4 | C34H35BrO5 |
|
| 溴[3-(四氢-2H-吡喃-2-基氧基)苯基]镁 | Magnesium bromide 3-[(oxan-2-yl)oxy]benzen-1-ide (1/1/1) | 142402-62-8 | C11H13BrMgO2 |
|
| 水合 6-甲基色酮 | 6-methyl-chromen-4-one | 38445-23-7 | C10H8O2 |
|
| 氧化白藜芦醇-3'-O-Beta-D-吡喃葡萄糖苷 | oxyresveratrol 3'-O-β-D-glucopyranoside | 144525-40-6 | C20H22O9 |
|
| 栎精-3-O-Β-D-吡喃葡萄糖基-6’’-乙酸盐 | quercetin 3-O-(6''-O-acetyl)-β-D-glucopyranoside | 54542-51-7 | C23H22O13 |
|
| 柠檬酸噻嘧啶 | pyrantel citrate | 5685-86-9 | C6H8O7*C11H14N2S |
|
| 松脂醇-4-O-beta-D-吡喃葡萄糖苷 | (+/-)-Pinoresinol-4'-O-β-D-monoglucoside | 24404-49-7 | C26H32O11 |
|
| 松脂醇 beta-D-吡喃葡萄糖苷 | pinoresinol-4'-O-β-D-glucopyranoside | 24404-49-7 | C26H32O11 |
|
| 曲酸 | 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one | 501-30-4 | C6H6O4 |
|
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