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 |
|---|---|---|---|---|
| 2,3,4,6-四-O-苯甲酰基葡萄糖三氯乙酰亚胺酯 | 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate | 151767-11-2 | C36H28Cl3NO10 |
|
| 2,3,4,6-四-O-苄基-1-C-二氯甲基-D-吡喃葡萄糖 | 2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-α-D-glucopyranose | 140658-50-0 | C35H36Cl2O6 |
|
| 2,3,4,6-四-O-乙酰基-α-D-叠氮化吡喃甘露糖 | 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl azide | 53784-29-5 | C14H19N3O9 |
|
| 2,3,4,6-四-O-乙酰基-Β-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 | 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate | 92052-29-4 | C16H20Cl3NO10 |
|
| 2,3,4,6-四-O-乙酰基-1-硫代-BETA-D-吡喃半乳糖 | 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose | 50615-66-2 | C14H20O9S |
|
| 2,3,4,6-O-四乙酰基-D-吡喃甘露糖 | 2,3,4,6-tetra-O-acetyl-D-mannopyranose | 140147-37-1 | C14H20O10 |
|
| 2,2-二甲基四氢吡喃-4-甲醛 | 2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde | 34941-21-4 | C8H14O2 |
|
| 2,2-二甲基-苯并二氢吡喃-4-酮 | 2,3-dihydro-2,2-dimethylbenzo[b]pyran-4-one | 3780-33-4 | C11H12O2 |
|
| 2(3)-(四氢糠基氧基)四氢吡喃 | tetrahydrofurfuryl tetrahydropyranyl ether | 710-14-5 | C10H18O3 |
|
| 1’,3’,3’-三甲基-6-羟基螺环 | 6-hydroxy spiropyran | 23001-29-8 | C19H19NO2 |
|
| 1-硫代-b-甲基葡萄糖甙-4-甲基苯酯 | p-methylphenyl 1-thio-β-D-glucopyranoside | 1152-39-2 | C13H18O5S |
|
| 1-硫代-ALPHA-D-吡喃甘露糖单钠盐 | sodium salt of 1-thio-α-D-mannose | 111057-34-2 | C6H11O5S*Na |
|
| 1-硫-乙基-2,3,4-三-氧-苄基-b-L-硫代呋喃岩藻糖苷 | ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside | 99409-34-4 | C29H34O4S |
|
| 1-叠氮基-1-脱氧-D-半乳糖醛酸酯2,3,4-三乙酸酯甲酯 | 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester | 67776-38-9 | C13H17N3O9 |
|
| 1-[2-[4-(2,2-二甲基-7-甲氧基-3-苯基色满-4-基)苯氧基]乙基]吡咯烷 | centchroman | 31477-60-8 | C30H35NO3 |
|
| 1-(四氢-2H-吡喃-4-基)乙醇 | 1-(tetrahydro-2H-pyran-4-yl)ethanol | 66956-74-9 | C7H14O2 |
|
| 1-(四氢-2H-吡喃-2-基)-1H-吡唑 | 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole | 449758-17-2 | C8H12N2O |
|
| 1-(2-氨基-4-甲基-1,3-噻唑-5-基)乙酮 | 5-acetyl-2-amino-4-(4-methoxyphenyl)-6-methyl-4H-pyran-3-carbonitrile | 105263-07-8 | C16H16N2O3 |
|
| 1,5-脱水-2,3,4-三脱氧-2-[[(1,1-二甲基乙氧基)羰基]氨基]-D-赤式己糖醇 | tert-butyl ((3R,6S)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate | 603130-12-7 | C11H21NO4 |
|
| 1,3,4,6-四-O-乙酰基-2-脱氧-2-[(2-叠氮乙酰基)氨基]-β-D-吡喃葡萄糖 | 1,3,4,6-tetra-O-acetyl-2-N-acetyl-2-deoxy-β-D-glucopyranose | 857677-98-6 | C16H22N4O10 |
|
| 1,3,4,6-四-O-乙酰基-2-氨基-alpha-D-吡喃葡萄糖盐酸盐 | 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride | 10034-19-2 | C14H21NO9*ClH |
|
| 1,3,4,6-TETRA-O-ACETYL-2-DEOXY-2-(2,2,2-TRICHLOROETHOXYCARBONYLAMINO)-Β-D-GLUCOPYRANOSE1,3,4,6-四-O-乙酰基-2-脱氧-2-(2,2,2-三氯乙氧)-Β-D-D-吡喃葡萄糖 | 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose | 122210-05-3 | C17H22Cl3NO11 |
|
| 1,2:3,4-二-o-异亚丙基-6-硫代-a-d-吡喃葡萄糖 | 1,2:3,4-di-O-isopropylidene-6-thio-α-D-galactopyranose | 16714-07-1 | C12H20O5S |
|
| 1,2:3,4-二-o-异亚丙基-6-o-对甲苯磺酰基-alpha-D-半乳糖 | (1,2:3,4-di-O-isopropylidene-6-O-(p-toluensulfonate))-D-galactopiranose | 4478-43-7 | C19H26O8S |
|
| 1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 | 1,2,4,6-tetra-O-acetyl-3-O-allyl-β-D-glucopyranose | 39698-00-5 | C17H24O10 |
|
| 1,2,3,4-四苄基-beta-d-吡喃葡萄糖 | benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside | 27851-29-2 | C34H36O6 |
|
| 1,2,3,4-四-O-乙酰-D-吡喃半乳糖苷 | D-1’,2’,3’,4’-tetracetyl galactopyranose | 78148-86-4 | C14H20O10 |
|
| 1,2,3,4,6-戊-O-苯甲酰基-D-吡喃甘露糖 | 1,2,3,4,6-penta-O-benzoyl-D-mannopyranose | 96996-90-6 | C41H32O11 |
|
| 1,1-二氧代-六氢-1L6-硫基吡喃-4-甲酸 | tetrahydro-2H-thiopyran-4-carboxylic acid 1,1-dioxide | 64096-87-3 | C6H10O4S |
|
| 1',3',3'-三甲基螺环-8-硝基(2H-1-苯并吡喃-2',2'-吲哚啉) | s.F. | 5150-50-5 | C19H18N2O3 |
|
| (四氢-2H-吡喃-4-基)甲醇 | (tetrahydro-2H-pyran-4-yl)methanol | 14774-37-9 | C6H12O2 |
|
| (rac)-6-亚甲基四氢吡喃-2-酮 | 6-methylidenetetrahydro-2-pyrone | 5636-66-8 | C6H8O2 |
|
| (S)-四氢-2H-吡喃-3-胺盐酸盐 | (S)-tetrahydro-2H-pyran-3-amine | 1071829-81-6 | C5H11NO |
|
| (S)-5-[(四氢吡喃基)氧基]-1-癸炔 | 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran | 223734-62-1 | C15H26O2 |
|
| (R)-四氢-2H-吡喃-3-胺盐酸盐 | (3R)-tetrahydropyran-3-amine | 1071829-82-7 | C5H11NO |
|
| (5,5-双(3,7-二甲基辛基)-5H-二噻吩[3,2-B:2',3'-D]吡喃-2,7-二基)双(三丁基锡) | ((5,5-bis(3,7-dimethyloctyl)-5H-dithieno[3,2-b:2',3'-d]pyran-2,7-diyl)bis(tributylstannane)) | 1295502-52-1 | C53H98OS2Sn2 |
|
| (4S)-3,4-二氢-2H-1-苯并吡喃-4-胺盐酸盐 | (S)-chroman-4-amine hydrochloride | 1035093-81-2 | C9H11NO*ClH |
|
| (4S)-3,4-二氢-2H-1-苯并吡喃-4-胺 | (S)-chroman-4-amine | 188198-38-1 | C9H11NO |
|
| (4R)-3,4-二氢-2H-1-苯并吡喃-4-胺 | (R)-chroman-4-amine | 210488-55-4 | C9H11NO |
|
| (4-甲基四氢-2H-吡喃-4-基)胺盐酸盐 | 4-methyltetrahydro-2H-pyran-4-amine hydrochloride | 851389-38-3 | C6H13NO*ClH |
|
| (4-氟四氢-2H-吡喃-4-基)甲胺 | (4-fluorotetrahydro-2H-pyran-4-yl)methanamine | 1228875-13-5 | C6H12FNO |
|
| (2R,3R,4S,5S,6R)-2-[(2E)-3,7-二甲基辛-2,6-二烯氧基]-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇 | geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside | 150995-11-2 | C21H36O10 |
|
| —— | 3-O-β-Glucosyl-platycodigenin | 38337-25-6 | C36H58O12 |
|
| —— | 3-{(E)-3-[4-(N,N-diethylamino)-2-hydroxyphenyl]prop-2-enoyl}-4-hydroxycoumarin | 1192030-17-3 | C22H21NO5 |
|
| —— | 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide | 102816-24-0 | C20H20N4O9 |
|
| —— | Galantamine metabolite M2 | 464189-54-6 | C22H27NO9 |
|
| —— | O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose | 99541-22-7 | C33H34O9 |
|
| —— | 22919-26-2 | C10H9NaO6P |
|
|
| —— | 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-galactopyranose | 72858-55-0 | C20H21NO10 |
|
| —— | 4-Nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid | 2872-66-4 | C20H23NO12 |
|
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