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 |
|---|---|---|---|---|
| 6-氯硫代苯并二氢吡喃-4-酮 | 6-chlorothiochroman-4-one | 13735-12-1 | C9H7ClOS |
|
| 6-氯-9-(四氢-2-吡喃基)嘌呤 | 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine | 7306-68-5 | C10H11ClN4O |
|
| 6-氯-4-羟基香豆素 | 6-chloro-4-hydroxycoumarin | 19484-57-2 | C9H5ClO3 |
|
| 6-氯-2-氧代-2H-苯并吡喃-3-羧酸 | 6-chloro-2-oxo-2H-chromene-3-carboxylic acid | 883-92-1 | C10H5ClO4 |
|
| 6-氨基-6-脱氧吡喃葡萄糖 | 6-amino-6-deoxy-D-glucose | 576-47-6 | C6H13NO5 |
|
| 6-氟-2-(环氧乙烷-2H)-3H,4H-苯并吡喃 | 6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran | 99199-90-3 | C11H11FO2 |
|
| 6-亚乙基八氢-5,8-甲桥-2H-1-苯并吡喃-2-酮 | 5,8-Methano-2H-1-benzopyran-2-one, 6-ethylideneoctahydro- | 69486-14-2 | C12H16O2 |
|
| 6-乙基-4-甲氧基-2H-吡喃-2-酮 | 6-ethyl-4-methoxy-2-pyrone | 106950-13-4 | C8H10O3 |
|
| 6-乙基-3-甲酰基色酮 | 6-ethyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde | 42059-78-9 | C12H10O3 |
|
| 6-(叔丁基二甲基硅氧基)-3,4-二氢-2H-吡喃 | 6-(tert-butyldimethylsilyloxy)-3,4-dihydro-2H-pyran | 130650-09-8 | C11H22O2Si |
|
| 6,8-二氯-3-氰基色酮 | 6,8-dichloro-4-oxo-4H-1-benzopyran-3-carbonitrile | 72798-32-4 | C10H3Cl2NO2 |
|
| 6,7-二甲氧基香豆素 | Scoparone | 120-08-1 | C11H10O4 |
|
| 6,7-二氟苯并二氢吡喃-4-酮 | 6,7-difluorochroman-4-one | 1092349-93-3 | C9H6F2O2 |
|
| 6,7,8,8alpha-四氢-2,5,5,8alpha-四甲基-5H-1-苯并吡喃 | 2,5,5,8a-Tetramethyl-6,7,8,8a-tetrahydro-5H-1-benzopyran | 5552-30-7 | C13H20O |
|
| 6,6,9-三甲基-3-丙基苯并[c]苯并吡喃-1-醇 | 6,6,9-trimethyl-3-propyl-6H-dibenzo[b,d]pyran-1-ol | 33745-21-0 | C19H22O2 |
|
| 5-碘-1-(四氢吡喃-2-基)吡唑 | 5-iodo-1-(tetrahydropyran-2-yl)pyrazole | 1311197-82-6 | C8H11IN2O |
|
| 5-乙酰氨基-7,8,9-三-O-乙酰基-5-N,4-O-羰基-3,5-二脱氧-2-S-苯基-2-硫代-Β-D-甘油-D-半乳-2-吡喃神经氨酸甲酯 | methyl (phenyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate | 934591-76-1 | C25H29NO12S |
|
| 5-乙酰基-2-氨基-6-甲基-4-苯基-4H-吡喃-3-甲腈 | 5-acetyl-2-amino-3-cyano-6-methyl-4-phenyl-4H-pyran | 89809-89-2 | C15H14N2O2 |
|
| 5-乙酰基-2-氨基-4-(2-呋喃基)-6-甲基-4H-吡喃-3-甲腈 | 5-acetyl-2-amino-4-furan-2-yl-6-methyl-4H-pyran-3-carbonitrile | 105263-08-9 | C13H12N2O3 |
|
| 5-(((四氢-2H-吡喃-2-基)氧基)甲基)间苯二甲酸 | 5-(tetrahydropyran-2-yloxymethyl)isophthalic acid | 1073561-04-2 | C14H16O6 |
|
| 5,7-二羟基-4-甲基香豆素 | 4-methyl-5,7-dihydroxycoumarin | 2107-76-8 | C10H8O4 |
|
| 5,7-二甲氧基香豆素 | Limettin | 487-06-9 | C11H10O4 |
|
| 5,6-二氢-7,8-二甲基-4,5-二氧代-4H-吡喃并[3,2-C]喹啉-2-甲酸 | MY 1250 | 63768-47-8 | C15H11NO5 |
|
| 5,6-二氢-4-羟基-6-甲基-2H-吡喃-2-酮 | 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one | 33177-29-6 | C6H8O3 |
|
| 5,6-二氢-4-甲氧基-2H-吡喃 | 4-methoxy-2,6-dihydropyran | 17327-22-9 | C6H10O2 |
|
| 5,6-二氢-3-乙氧羰基-2-甲基-4H-吡喃 | ethyl 6-methyl-3,4-dihydro-2H-pyran-5-carboxylate | 10226-28-5 | C9H14O3 |
|
| 5,5-双（3,7-二甲基辛基）-5H-二硫代[3,2-b：2'，3'-d]吡喃 | 5-(3,7-dimethyloctyl)-5-(3-methyloctyl)-5Hdithieno[3,2-b:2',3'-d]pyran | 1295502-20-3 | C29H46OS2 |
|
| 4H-1-苯并吡喃-4-酮, 2,3-二氢-5,7-二甲氧基 | 5,7-dimethoxychroman-4-one | 54107-66-3 | C11H12O4 |
|
| 4-（二巯基亚甲基）-2-甲基-6-（对二甲氨基苯乙烯基）-4H-吡喃 | 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran | 51325-91-8 | C19H17N3O |
|
| 4-醛基四氢吡喃 | 3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde | 50675-18-8 | C6H10O2 |
|
| 4-苯基四氢吡喃-4-羧酸 | 4-phenyltetrahydro-2H-pyran-4-carboxylic acid | 182491-21-0 | C12H14O3 |
|
| 4-苯基-四氢-2H-吡喃4-酮 | 4-phenyltetrahydro-2H-pyran-4-ol | 81462-07-9 | C11H14O2 |
|
| 4-羟基香豆素 | 4-hydroxy[1]benzopyran-2-one | 1076-38-6 | C9H6O3 |
|
| 4-羟基-6-甲基-2-吡喃酮 | 4-hydroxy-6-methyl-2-pyron | 675-10-5 | C6H6O3 |
|
| 4-碘四氢-2H-吡喃 | 4-iodotetrahydropyran | 25637-18-7 | C5H9IO |
|
| 4-碘-1-(四氢吡喃-2-基)-1H-吡唑 | 4-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole | 938066-17-2 | C8H11IN2O |
|
| 4-硝基苯基2,3,4,6-四-O-乙酰基-alpha-D-吡喃甘露糖苷 | p-Nitrophenyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 13242-51-8 | C20H23NO12 |
|
| 4-硝基苯基-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷 | 4-nitrophenyl 2-acetamido-2-deoxy-α-D-galactopyranoside | 23646-68-6 | C14H18N2O8 |
|
| 4-硝基苯基-2-乙酰氨基-2-脱氧-3-(β-吡喃半乳糖)-β-D-半乳糖苷 | 4-nitrophenyl (O-β-D-galactopyranosyl)-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranoside | 57467-13-7 | C20H28N2O13 |
|
| 4-甲酰胺基吡喃 | tetrahydro-pyran-4-carboxylic acid amide | 344329-76-6 | C6H11NO2 |
|
| 4-甲氧苯基4,6-O-苯亚甲基-Β-D-吡喃半乳糖苷 | 4-Methoxyphenyl 4,6-O-Benzylidene-beta-D-galactopyranoside | 176299-96-0 | C20H22O7 |
|
| 4-甲氧苯基3-O-苄基-2-脱氧-2-苯二甲酰亚氨基-Β-D-吡喃葡萄糖苷 | para-MethoxyPhenyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 138906-44-2 | C28H27NO8 |
|
| 4-甲氧苯基3-O-烯丙基-2-叠氮基-4,6-O-苯亚甲基-2-脱氧-Β-D-吡喃半乳糖苷 | 4-Methoxyphenyl 3-O-Allyl-2-azido-4,6-O-benzylidene-2-deoxy-beta-D-galactopyranoside | 889453-83-2 | C23H25N3O6 |
|
| 4-甲氧苯基2,4,6-三-O-乙酰-3-O-苄基-β-D-吡喃葡萄糖苷 | 4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside | 303127-79-9 | C26H30O10 |
|
| 4-甲氧苯基-4-O-乙酰基-3,6-二-O-苄基-2-脱氧-2-苯二甲酰亚氨基-β-D-吡喃葡萄糖苷 | 4-methoxyphenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 140615-77-6 | C37H35NO9 |
|
| 4-甲氧苯基-3-O-苄基-β-D-吡喃葡萄糖苷 | 4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside | 303127-80-2 | C20H24O7 |
|
| 4-甲氧苯基-3-O-苄基-β-D-吡喃半乳糖苷 | 4-Methoxyphenyl 3-O-Benzyl-beta-D-galactopyranoside | 383905-60-0 | C20H24O7 |
|
| 4-甲氧苯基-3-O-苄基-4,6-O-苯亚甲基-β-D-吡喃葡萄糖苷 | p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside | 303127-81-3 | C27H28O7 |
|
| 4-甲氧苯基-3-O-烯丙基-4,6-O-苯亚甲基-2-脱氧-2-邻苯二甲酰亚氨基-β-D-吡喃葡萄糖苷 | 4-Methoxyphenyl 3-O-Allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside | 889453-84-3 | C31H29NO8 |
|
| 4-甲氧苯基-3,6-二-O-苄基-2-脱氧-2-苯二甲酰亚氨基-β-D-吡喃葡萄糖苷 | p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 129575-89-9 | C35H33NO8 |
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