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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2-羟甲基-3,4-二氢吡喃 | 2-hydroxymethyl-3,4-dihydro-2H-pyran | 3749-36-8 | C6H10O2 |
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2-羟基-5-[[(2R,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氨基]苯甲酸 | N-Glucopyranosyl-5-aminosalicylic acid | 123135-21-7 | C13H17NO8 |
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2-甲氧基四氢吡喃 | 2-methoxytetrahydropyran | 6581-66-4 | C6H12O2 |
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2-甲基丙烯酸酯-4氢吡喃 | 3,4,5,6-tetrahydropyran-2-yl methacrylate | 52858-59-0 | C9H14O3 |
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2-甲基-5,6-二氢-4H-吡喃-3-羧酸 | 6-methyl-3,4-dihydro-2H-pyran-5-carboxylic acid | 5399-21-3 | C7H10O3 |
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2-氯-四氢-2H-吡喃 | 2-chlorotetrahydro-2H-pyran | 3136-02-5 | C5H9ClO |
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2-氯-4-硝基苯基-beta-D-葡糖-吡喃糖苷 | 2-chloro-4-nitrophenyl β-D-glucopyranoside | 120221-14-9 | C12H14ClNO8 |
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2-氨基-6-氯-3-甲酰色酮 | 2-amino-6-chloro-4-oxo-4H-1-benzopyran-3-carboxaldehyde | 68301-77-9 | C10H6ClNO3 |
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2-氨基-3-甲酰色酮 | 2-amino-3-formylchromone | 61424-76-8 | C10H7NO3 |
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2-氨基-2-脱氧-beta-D-吡喃葡萄糖基-(1->4)-(4Xi)-2-氨基-2-脱氧-D-木糖基-己糖吡喃糖苷-(1->4)-2-氨基-2-脱氧-beta-D-吡喃葡萄糖 | isopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 78341-33-0 | C11H21NO6 |
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2-氧代-2H-吡喃-3-甲酸甲酯 | methyl 2-oxo-2H-pyrane-3-carboxylate | 25991-27-9 | C7H6O4 |
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2-对溴苯氧基四氢吡喃 | 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene | 36603-49-3 | C11H13BrO2 |
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2-四氢吡喃酸 | tetrahydropyran-2-carboxylic acid | 51673-83-7 | C6H10O3 |
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2-四氢吡喃-4-乙醇 | 2-(tetrahydropyran-4-yl)-ethanol | 4677-18-3 | C7H14O2 |
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2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯 | 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose | 171032-74-9 | C14H19N3O9 |
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2-叠氮基-2-脱氧-3,4-二-O-苄基-beta-D-吡喃葡萄糖 6-乙酸酯 | 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose | 157896-03-2 | C22H25N3O6 |
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2-乙酰氨基-2,4-二脱氧-4-氟-d-吡喃葡萄糖 | 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose | 116049-57-1 | C14H20FNO8 |
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2-乙酰氨基-2,4-二脱氧-4-氟-D-吡喃半乳糖 | allyl 2-acetamido-2,4-dideoxy-4-fluoro-α-D-galactopyranoside | 129728-92-3 | C8H14FNO5 |
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2-乙氧基-3,4-二氢吡喃 | 2-ethoxy-2,3-dihydro-4H-pyran | 103-75-3 | C7H12O2 |
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2-丙烯氧基吡喃 | 2-(prop-2-en-1-yloxy)oxane | 4203-49-0 | C8H14O2 |
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2-[(5-氯戊基)氧基]四氢-2H-吡喃 | 2-[(5-chloropentyl)oxy]tetrahydropyran | 13129-60-7 | C10H19ClO2 |
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2-PROPENYL4,6-O-BENZYLIDENE-Α-D-GLUCOPYRANOSIDE2-丙烯基4,6-O-亚苄基-Α-D-吡喃葡萄糖苷 | allyl 4,6-O-benzylidene-α-D-glucopyranoside | 93382-48-0 | C16H20O6 |
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2-N-Boc-氨基-3-(4-四氢吡喃基)丙酸 | 2-((tert-butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propanoic acid | 182287-51-0 | C13H23NO5 |
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2-(四氢-2H-吡喃-2-氧基)乙醇 | 2-(tetrahydropyran-2-yloxy)ethanol | 2162-31-4 | C7H14O3 |
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2-(乙酰氨基)-2-脱氧-alpha-D-吡喃半乳糖基氯化物 3,4,6-三乙酸酯 | 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride | 41355-44-6 | C14H20ClNO8 |
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2-(7-二乙基氨基)-2-氧代-2H-1-苯并吡喃-3-基)-5-苯并恶唑亚磺酰胺 | 3-(5'-sulfonylamine-2'-benzoxazole)-7-diethylamino-2H-1-benzopyran-2-one | 68427-35-0 | C20H19N3O5S |
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2-(6-溴己氧基)四氢吡喃 | 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran | 53963-10-3 | C11H21BrO2 |
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2-(6-氯己氧基)四氢-2H-吡喃 | (chloro-6' hexyloxy)-2 tetrahydropyranne | 2009-84-9 | C11H21ClO2 |
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2-(4-戊炔氧基)四氢-2H-吡喃 | 1-(tetrahydropyranyloxy)-4-pentyn | 62992-46-5 | C10H16O2 |
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2-(3-溴苯氧基)四氢-2H-吡喃 | 3-(tetrahydropyran-2-yloxy)phenyl bromide | 57999-49-2 | C11H13BrO2 |
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2-(3-溴丙氧基)四氢-2H-吡喃 | 3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide | 33821-94-2 | C8H15BrO2 |
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2-(3-氯丙氧基)四氢-2H-吡喃 | 1-chloro-3-(2-tetrahydropyranyloxy)propane | 42330-88-1 | C8H15ClO2 |
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2-(3-丁炔氧基)四水-2H-吡喃 | 2-(but-3-yn-1-yloxy)tetrahydropyran | 40365-61-5 | C9H14O2 |
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2-(3,4-二羟基苯基)-3,5,7-三羟基-6-甲氧基-4-苯并吡喃酮 | patuletin | 519-96-0 | C16H12O8 |
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2-(3,4,5-三甲氧基苯基)铬-4-酮 | 2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one | 67858-30-4 | C18H16O5 |
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2-(2-硝基乙氧基)四氢吡喃 | 2-(2-nitroethoxy)tetrahydro-2H-pyran | 75233-61-3 | C7H13NO4 |
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2-(2-溴乙氧基)四氢吡喃 | 2-(2-bromoethoxy)tetrahydropyran | 17739-45-6 | C7H13BrO2 |
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2-(2-氯乙氧基)四氢-2H-吡喃 | 2-(2-chloroethoxy)-tetrahydro-2H-pyrane | 5631-96-9 | C7H13ClO2 |
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2-(2-氧代-苯并吡喃-7-基氧基)丙酸 | 2-[(2-Oxo-2H-chromen-7-YL)oxy]propanoic acid | 304889-93-8 | C12H10O5 |
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2-(2-叔丁基-6-甲基-4-吡喃亚基)丙二腈 | 2-(2-(tert-butyl)-6-methyl-4H-pyran-4-ylidene)malononitrile | 225378-53-0 | C13H14N2O |
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2-(2,3-二羟基苯基)-4H-苯并吡喃-4-酮 | 2',3'-dihydroxyflavone | 2554-85-0 | C15H10O4 |
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2,6-二氢-6-羟基-3(3H)-吡喃酮 | 6-hydroxy-3,6-dihydro-2H-pyran-3-one | 35436-57-8 | C5H6O3 |
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2,4-噁唑烷二酮,5-甲基-5-苯乙基-(6CI) | ormeloxifene | 31477-60-8 | C30H35NO3 |
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2,4,6-三苯基吡喃四氟化硼盐 | 2,4,6-Triphenylpyrylium tetrafluoroborate | 448-61-3 | C23H17BF4O |
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2,3-二氢苯并吡喃-4-酮 | 2,3-dihydro-4H-1-benzopyran-4-one | 491-37-2 | C9H8O2 |
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2,3-二氢-吡喃-5-羧酸 | 3,4-dihydro-2H-pyran-5-carboxylic acid | 40915-37-5 | C6H8O3 |
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2,3,5,6-四甲基四氢吡喃-4-酮 | 2,3,5,6-tetrahydro-2,3,5,6-tetramethyl-γ-pyrone | 54458-60-5 | C9H16O2 |
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2,3,4-三-O-苄基吡喃葡萄糖醛酸苄酯 | Benzyl 2,3,4-tri-o-benzyl-d-glucopyranosyluronate | 4539-78-0 | C34H34O7 |
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2,3,4,6-四邻乙酰基-alpha-d-吡喃甘露糖氟化物 | 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride | 2823-44-1 | C14H19FO9 |
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2,3,4,6-四苄基-D-吡喃葡萄糖 | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose | 4132-28-9 | C34H36O6 |
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