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 |
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曲格列酮 | Troglitazone | 97322-87-7 | C24H27NO5S |
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异金雀花素-2"-O-吡喃葡萄糖苷 | Isoscoparin-2"-beta-D-glucopyranoside | 97605-25-9 | C28H32O16 |
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异茴芹内酯 | isopimpinellin | 482-27-9 | C13H10O5 |
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异苯并二氢吡喃-4-醇 | Isochromanol-4 | 20924-57-6 | C9H10O2 |
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异色满 | isochromane | 493-05-0 | C9H10O |
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左美洛昔芬 | ormeloxifene | 78994-23-7 | C30H35NO3 |
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山柰酚-3-O-(2,6-二-O-反式-对香豆酰基)-beta-D-吡喃葡萄糖苷 | kaempferol 3-O-[2'',6''-di-O-(trans-p-coumaroyl)]-β-D-glucopyranoside | 121651-61-4 | C39H32O15 |
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山柰酚 3-O-(6-O-没食子酰)-beta-D-吡喃葡萄糖苷 | 6''-O-(3,4,5-trihydroxybenzoyl) 3-O-β-D-glucopyranosyloxy-4',5,7-trihydroxyflavone | 56317-05-6 | C28H24O15 |
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奈比洛尔杂质 | [1S*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene | 793669-26-8 | C11H11FO2 |
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四氢噻喃-4-酮 1,1-二氧化物 | 1,1-dioxotetrahydrothiopyran-4-one | 17396-35-9 | C5H8O3S |
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四氢噻喃-4-酮 | Tetrahydrothiopyran-4-one | 1072-72-6 | C5H8OS |
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四氢吡喃酮 | Tetrahydro-4H-pyran-4-one | 29943-42-8 | C5H8O2 |
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四氢吡喃-4-醇 | Tetrahydro-pyran-4-ol | 2081-44-9 | C5H10O2 |
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四氢吡喃-4-羧酸甲酯 | tetrahydropyran-4-carboxylic acid methyl ester | 110238-91-0 | C7H12O3 |
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四氢吡喃-4-羧酸乙酯 | ethyl tetrahydro-2H-pyran-4-carboxylate | 96835-17-5 | C8H14O3 |
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四氢吡喃-4-甲酸 | Tetrahydropyran-4-carboxylic acid | 5337-03-1 | C6H10O3 |
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四氢吡喃-4-基-乙酸乙酯 | ethyl tetrahydropyran-4-acetate | 103260-44-2 | C9H16O3 |
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四氢吡喃-4-乙酸 | 2-(tetrahydro-2H-pyran-4-yl)acetic acid | 85064-61-5 | C7H12O3 |
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四氢吡喃-4-乙酰氯 | 2-(tetrahydro-2H-pyran-4-yl)acetyl chloride | 40500-05-8 | C7H11ClO2 |
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四氢吡喃-4,4-二羧酸 | tetrahydro-4H-pyran-4,4-dicarboxylic acid | 5337-04-2 | C7H10O5 |
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四氢吡喃-4,4-二甲酸二甲酯 | 4,4-dimethyl dihydro-2H-pyran-4,4(3H)-dicarboxylate | 149777-00-4 | C9H14O5 |
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四氢吡喃-2-甲醇 | Tetrahydropyran-2-methanol | 100-72-1 | C6H12O2 |
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四氢吡喃 | Oxane | 142-68-7 | C5H10O |
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四氢-4-氧代-2H-噻喃-3-甲酸甲酯 | 3-methoxycarbonyltetrahydropyran-4-one | 4160-61-6 | C7H10O3S |
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四氢-2H-吡喃-3-酮 | 5,6-dihydro-2H-pyran-3(4H)-one | 23462-75-1 | C5H8O2 |
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四氢-2-苯基-4H-吡喃-4-酮 | 2-phenyltetrahydropyran-4-one | 147688-62-8 | C11H12O2 |
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四氢-2 2-二甲基-4H-吡喃-4-酮 | 2,2-dimethyltetrahydropyran-4-one | 1194-16-7 | C7H12O2 |
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哌喃 | 3-(tetrahydropyran-2'-yloxy)propyne | 6089-04-9 | C8H12O2 |
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吡喃-4-酮 | 4-pyrone | 108-97-4 | C5H4O2 |
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依折麦布四氢吡喃 | (2R,3R,6S)-N,6-bis(4-fluorophenyl)-2-(4-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-3-carboxamide | 1296129-15-1 | C24H21F2NO3 |
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佛手苷内酯 | bergapten | 484-20-8 | C12H8O4 |
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二甲基甲氧基苯并二氢吡喃醇 | 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran | 83923-51-7 | C12H16O3 |
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二甲基伞形酮 | 3,4-dimethyl-7-hydroxycoumarin | 2107-78-0 | C11H10O3 |
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二(四氢吡喃-4-基)胺 | bis(tetrahydro-2H-pyran-4-yl)amine | 1080028-76-7 | C10H19NO2 |
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乙基3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷 | ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 99409-32-2 | C22H25NO9S |
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乙基2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷 | ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 130539-43-4 | C16H19NO6S |
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中文名称暂缺 | Diethylstilbestrol monoglucuronide | 2408-40-4 | C24H28O8 |
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Α-D-氟代吡喃甘露糖 | α-D-mannopyranosyl fluoride | 2713-54-4 | C6H11FO5 |
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Α-D-吡喃半乳糖基苯基异硫氰酸酯 | alpha-D-Galactopyranosylphenyl isothiocyanate | 120967-92-2 | C13H15NO6S |
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n-[四氢-2H-硫代吡喃-4-基]氨基甲酸-1,1-二甲基乙酯 | tert-butyl (tetrahydro-2H-thiopyran-4-yl)carbamate | 595597-00-5 | C10H19NO2S |
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[4-(四氢吡喃-2-基)氧基]苯硼酸 | 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid | 182281-01-2 | C11H15BO4 |
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[(2-氧代-2H-苯并吡喃-7-基)氧基]乙酸 | 2-((2-oxo-2H-chromen-7-yl)oxy)acetic acid | 126424-85-9 | C11H8O5 |
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P-[[(四氢-2H-吡喃-2-基)氧基]甲基]-膦酸二乙酯 | diethyl <<(2-tetrahydropyranyl)oxy>methyl>phosphonate | 71885-51-3 | C10H21O5P |
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O-(四氢-2H-吡喃-2-基)羟基胺 | O-2-tetrahydro-2H-pyranhydroxylamine | 6723-30-4 | C5H11NO2 |
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N-(ε-N-苄氧基羰基氨基)己酰基)-β-D-吡喃半乳糖苷(含有约35%的乙醇) | Benzyl N-[6-oxo-6-[[(2R,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]hexyl]carbamate | 38822-58-1 | C20H30N2O8 |
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N-甲基四氢-2H-吡喃-4-胺 | N-methyl-N-(tetrahydropyran-4-yl)amine | 220641-87-2 | C6H13NO |
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N-[(ε-苄氧基羰基氨基)己酰基]-β-L-呋喃核糖胺 | N-[(epsilon-Benzyloxycarbonylamino)caproyl]-beta-L-fucopyranosylamine | 35978-96-2 | C20H30N2O7 |
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N-(四氢-2H-吡喃-2-氧基)琥珀酰亚胺 | N-(tetrahydropyranyloxy)succinimide | 55610-40-7 | C9H13NO4 |
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N-(5-氯苯并[d][1,3]二氧代l-4-基)-7-氟-5-((四氢-2H-吡喃-4-基)氧基)喹唑啉-4-胺 | 7-fluoro-N-(5-chloro-1,3-benzodioxol-4-yl)-5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine | 379230-38-3 | C20H17ClFN3O4 |
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N-(2-氰基-4-氧代-4H-1-苯并吡喃-8-基)-4-(4-苯基丁氧基)苯甲酰胺 | N-(2-cyano-4-oxo-4H-chromen-8-yl)-4-(4-phenylbutoxy)benzamide | 136450-11-8 | C27H22N2O4 |
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