异喹啉是一种含苯环和吡啶环的杂环化合物,是喹啉的一种同分异构体,即由萘分子中β位的CH基被N原子取代而成。它通常呈现为无色至浅黄色的液体或片状结晶,并带有类似茴香油和苯甲醛的刺激性气味,具有较强的吸水性和较高的碱性。化学性质活泼,能够发生亲核、亲电、氧化及还原反应。许多生物碱如罂粟碱、小蘖碱和吗啡碱等分子中均含有异喹啉或氢化异喹啉的基本结构。
异喹啉的应用广泛:可用作聚亚胺薄膜溶剂;有机导电体、染料、感光色素、杀虫剂、生物碱及医药制品的原料;通过氧化反应制备吡啶羧酸;而异喹啉盐酸盐则常用于测定锌、镉、钴和铜等金属;此外,还可以用来制备各种异喹啉衍生物。
其合成方法包括:一种于1893年提出的Bischler法。该方法以β-苯乙胺的酰基化物为原料,在五氧化二磷(或ZnCl2、POCl3等)的作用下脱水缩合闭环,生成3,4-二氢异喹啉;然后在钯催化作用下于190℃条件下进行氧化脱氢反应以制备异喹啉。另一种方法则是通过肉桂醛肟的Beckmann重排,在五氧化二磷(或硫酸、多聚磷酸)的作用下进行闭环生成所需产物。
中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
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1,2,3,4-四氢异喹啉-7-醇 | 7-hydroxy-1,2,3,4-tetrahydroisoquinoline | 30798-64-2 | C9H11NO |
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1,2,3,4-四氢异喹啉-7-羧酸盐甲酯盐酸盐 | methyl 1,2,3,4-tetrahydroisoquinoline-7-carboxylate hydrochloride | 220247-69-8 | C11H13NO2*ClH |
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1,2,3,4-四氢异喹啉-3-羧酸甲酯 | 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid | 57060-86-3 | C11H13NO2 |
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1,2,3,4-四氢异喹啉-1-羧酸 | 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid | 41034-52-0 | C10H11NO2 |
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1,2,3,4-四氢-6,7-二甲氧基-2-[2-(4-硝基苯基)乙基]异喹啉 | 6,7-dimethoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydroisoquinoline | 82925-01-7 | C19H22N2O4 |
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1,2,3,4-四氢-5-异喹啉羧酸甲酯盐酸盐 | 1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid methyl ester hydrochloride | 1035700-06-1 | C11H13NO2*ClH |
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1,2,3,4-四氢-2-甲基-7-异喹啉胺 | 7-amino-2-methyl-1,2,3,4-tetrahydroisoquinoline | 14097-40-6 | C10H14N2 |
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1(2H)-异喹啉-4,7-氨基(9CI) | 7-aminoisoquinolin-1(2H)-one | 174302-46-6 | C9H8N2O |
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(异喹啉-7-基)甲胺 | (Isoquinolin-7-YL)methanamine | 1053655-96-1 | C10H10N2 |
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(异喹啉-6-基)甲醇 | (isoquinolin-6-yl)methanol | 188861-59-8 | C10H9NO |
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(异喹啉-6-基)甲胺 | isoquinolin-6-ylmethanamine | 1053655-94-9 | C10H10N2 |
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(S)-N-叔丁基-1,2,3,4-四氢异喹啉-3-甲酰胺 | (S)-N-tert-butyl-1,2,3,4-tetrahydro-3-isoquinoline-carboxamide | 149182-72-9 | C14H20N2O |
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(S)-6,7-二甲氧基-1,2,3,4-四氢-3-异喹啉羧酸盐酸盐 | (S)-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid | 103733-66-0 | C12H15NO4 |
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(S)-1-甲基-1,2,3,4-四氢异喹啉 | (-)-1-methyl-1,2,3,4-tetrahydro-isoquinoline | 4965-09-7 | C10H13N |
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(R)-1-苯基-1,2,3,4-四氢异喹啉 | (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline | 180272-45-1 | C15H15N |
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(7S)-1,2,3,10-四甲氧基-7-(甲基氨基)-6,7-二氢苯并[a]庚搭烯-9(5H)-酮 | 6,7-dimethoxy-1-(3,4,5-trimethoxybenzyl)-3,4-dihydroisoquinoline | 61349-11-9 | C21H25NO5 |
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—— | 7-Brommethyl-biphenylen-2-aldehyd | 10172-39-1 | C14H9BrO |
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—— | 2-Benzyl-2,3-dihydro-4(1H)-isochinolon | 53667-19-9 | C16H15NO |
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—— | tert-butyl (S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate | 103733-66-0 | C16H23NO4 |
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—— | 1,2,3,4-Tetrahydroisoquinolin-2-ium-6,7-diol | 52768-23-7 | C9H12NO2+ |
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—— | Iridium(3+) tris(2-(isoquinolin-1-yl)benzen-1-ide) | 435293-93-9 | C45H30IrN3 |
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—— | 1,3-Dichloroisoquinolin-4-amine | 912773-27-4 | C9H6Cl2N2 |
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—— | 3-aminoisoquinoline-6-carboxylic acid | 1337880-79-1 | C10H8N2O2 |
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—— | 1-Iodoisoquinolin-5-amine | 1260759-47-4 | C9H7IN2 |
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—— | Isoquinolin-4-ol hydrochloride | 15365-53-4 | C9H8ClNO |
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—— | 7-chloroisoquinoline-1(2H)-thione | 130874-99-6 | C9H6ClNS |
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—— | 6-benzyloxy-1,2,3,4-tetrahydro-isoquinoline | 252061-94-2 | C16H17NO |
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—— | 3-[(tert-Butylimino)(hydroxy)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium | 149182-72-9 | C14H21N2O+ |
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—— | 1-(6-isoquinolyl)ethan-1-one | 1015070-54-8 | C11H9NO |
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—— | 5-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline | 215788-34-4 | C10H10F3N |
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—— | ethyl 5-bromoisoquinoline-1-carboxylate | 1111311-65-9 | C12H10BrNO2 |
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—— | trans-decahydroisoquinoline | 2744-09-4 | C9H17N |
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