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 |
|---|---|---|---|---|
| B-D-五苯甲酸酰葡萄糖 | Penta-O-benzoyl-β-D-galactopyranose | 2592-58-7 | C41H32O11 |
|
| 9-甲氧基-2,3-二氢-7H-呋喃并[3,2-g]苯并吡喃-7-酮 | 2,3-Dihydroxanthotoxin | 3779-03-1 | C12H10O4 |
|
| 9-[[3,4,6-三-O-乙酰基-2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-beta-D-吡喃葡萄糖基]氧基]壬酸乙酯 | 8-ethoxycarbonyloctyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 106445-23-2 | C31H41NO12 |
|
| 8-溴-2H-1-苯并吡喃-2-酮 | 8-bromocoumarin | 33491-30-4 | C9H5BrO2 |
|
| 8-氨基-4-酮-2-(四氮唑-5-基)-4H-1-苯并吡喃盐酸盐 | 8-amino-2-tetrazol-5-yl-4-oxo-4H-1-benzopyran | 110683-23-3 | C10H7N5O2*ClH |
|
| 8-氨基-2-(1H-四唑-5-基)-4H-1-苯并吡喃-4-酮 | 8-amino-2-tetrazol-5-yl-4-oxo-4H-1-benzopyran | 110683-22-2 | C10H7N5O2 |
|
| 8-乙酰基-7-羟基香豆素 | 8-acetyl-7-hydroxycoumarin | 6748-68-1 | C11H8O4 |
|
| 8-乙酰-7-甲氧基香豆素 | 8-acetyl-7-methoxy-2H-chromen-2-one | 89019-07-8 | C12H10O4 |
|
| 8-乙基-1,3,4,9-四氢-1-甲基吡喃并[3,4-b]吲哚-1-乙酸 | (8-ethyl-1-methyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)acetic acid | 109518-47-0 | C16H19NO3 |
|
| 7-羟基香豆素-3-羧酸乙酯 | 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester | 6093-71-6 | C12H10O5 |
|
| 7-羟基香豆素-3-羧酸 | 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid | 779-27-1 | C10H6O5 |
|
| 7-羟基-4-甲基-3-香豆素乙酸 | (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid | 5852-10-8 | C12H10O5 |
|
| 7-羟基-4-氧代-4H-苯并吡喃-2-羧酸乙酯 | ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate | 23866-72-0 | C12H10O5 |
|
| 7-羟基-4-三氟甲基香豆素 | 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one | 575-03-1 | C10H5F3O3 |
|
| 7-羟基-3-苯基-2H-苯并吡喃-2-酮 | 7-Hydroxy-3-phenyl-chromen-2-one | 6468-96-8 | C15H10O3 |
|
| 7-羟基-2-氧代-2H-苯并吡喃-3-甲酸甲酯 | methyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate | 86788-49-0 | C11H8O5 |
|
| 7-疏基-4-甲基香豆素 | 7-mercapto-4-methyl-2H-chromen-2-one | 137215-27-1 | C10H8O2S |
|
| 7-甲氧基-4-甲基香豆素 | 4-methyl-7-methoxy-2H-1-benzopyran-2-one | 2555-28-4 | C11H10O3 |
|
| 7-甲氧基-4,4-二甲基-1,3-异苯并吡喃二酮 | 4,4-Dimethyl-7-methoxyisochroman-1,3-dione | 55974-25-9 | C12H12O4 |
|
| 7-甲氧基-2-氧代-2H-1-苯并吡喃-4-乙酸 | 2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetic acid | 62935-72-2 | C12H10O5 |
|
| 7-溴-2H-1-苯并吡喃-2-酮 | 7-bromo-2H-chromen-2-one | 19063-56-0 | C9H5BrO2 |
|
| 7-氨基-4-(甲氧基甲基)香豆素 | 4-methoxymethyl-7-aminocoumarin | 175205-10-4 | C11H11NO3 |
|
| 7-氟-4-羟基-2H-吡喃-2-酮 | 7-fluoro-4-hydroxy-2H-chromen-2-one | 2145-27-9 | C9H5FO3 |
|
| 7-二甲氨基-4-甲基香豆素 | 7-dimethylamino-4-methyl-chromen-2-one | 87-01-4 | C12H13NO2 |
|
| 7-二乙基氨基-3-噻吩甲酰基香豆素 | 7-diethylamino-3-thenoylcoumarin | 77820-11-2 | C18H17NO3S |
|
| 7-乙酰氧基-4-溴甲基香豆素 | 7-acetoxy-4-bromomethyl-2H-1-benzopyran-2-one | 2747-04-8 | C12H9BrO4 |
|
| 7-乙氧基香豆素 | 7-ethoxycoumarin | 31005-02-4 | C11H10O3 |
|
| 7-丙氧基-苯并吡喃-2-酮 | 7-propoxycoumarin | 6093-73-8 | C12H12O3 |
|
| 7-[[4-氯-6-(二乙基氨基)-1,3,5-三嗪-2-基]氨基]-3-苯基-2-苯并吡喃酮 | 7-<<4-chloro-6-(diethylamino)-s-triazin-2-yl>amino>-3-phenylcoumarin | 5516-22-3 | C22H20ClN5O2 |
|
| 7-(羧基甲氧基)-4-甲基香豆素 | 7-(carboxymethoxy)-4-methylcoumarin | 64700-15-8 | C12H10O5 |
|
| 7,8-二羟基-4-甲基香豆素 | 4-methyldaphnetin | 2107-77-9 | C10H8O4 |
|
| 7,8-二羟基-3-(4-羟基苯基)苯并吡喃-4-酮 | 8-hydroxydaidzein | 75187-63-2 | C15H10O5 |
|
| 7,8-二氢-5H-吡喃并[4,3-D]嘧啶-2-胺 | 7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine | 1211486-21-3 | C7H9N3O |
|
| 6-苄氨基-9-(Α-D-吡喃葡萄糖基)嘌呤 | 6-benzylamino-9-beta-D-glucopyranosylpurine | 4294-17-1 | C18H21N5O5 |
|
| 6-羧基香豆素 | 2-oxo-2H-chromene-6-carboxylic acid | 7734-80-7 | C10H6O4 |
|
| 6-羟基黄烷酮 | 6-hydroxyflavanone | 4250-77-5 | C15H12O3 |
|
| 6-甲氧基香豆素-7-0-beta-D-吡喃葡萄糖苷 | 7-methoxycoumarin-6-β-D-glucopyranoside | 20186-29-2 | C16H18O9 |
|
| 6-甲基硫代苯并二氢吡喃-4-酮 | 6-methyl-thiochroman-4-one | 6948-34-1 | C10H10OS |
|
| 6-甲基-5,6-二氢-2H-吡喃-2-酮 | parasorbic acid | 108-54-3 | C6H8O2 |
|
| 6-溴香豆素-3-甲酸 | 6-bromocoumarin-3-carboxylic acid | 2199-87-3 | C10H5BrO4 |
|
| 6-溴苯并二氢吡喃 | 6-bromochromane | 3875-78-3 | C9H9BrO |
|
| 6-溴色原酮 | 6-bromo-1-benzopyran-4(4H)-one | 51483-92-2 | C9H5BrO2 |
|
| 6-溴-4-二氢色原酮 | 6-bromochroman-4-one | 49660-57-3 | C9H7BrO2 |
|
| 6-溴-4,4-二甲基硫代苯并二氢吡喃 | 6-bromo-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran | 112110-44-8 | C11H13BrS |
|
| 6-溴-3-甲酰色酮 | 6-bromo-4-oxo-4H-chromene-3-carbaldehyde | 52817-12-6 | C10H5BrO3 |
|
| 6-溴-3-氰色酮 | 6-bromochromone-3-carbonitrile | 52817-13-7 | C10H4BrNO2 |
|
| 6-溴-3-氰基-4-甲基香豆素 | 6-bromo-4-methyl-2-oxo-2H-chromene-3-carbonitrile | 56394-22-0 | C11H6BrNO2 |
|
| 6-溴-3-丁酰-2H-苯并吡喃-2-酮 | 6-bromo-3-butyryl-coumarin | 2199-83-9 | C13H11BrO3 |
|
| 6-溴-2-苯基-(4H)-4-苯并吡喃酮 | 6-bromoflavone | 1218-80-0 | C15H9BrO2 |
|
| 6-氯色酮-3-腈 | 6-chloro-3-cyanochromone | 50743-20-9 | C10H4ClNO2 |
|
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