喹啉和异喹啉是苯并吡啶的两个异构体,均存在于煤焦油中。它们及其许多取代衍生物可通过将苯衍生物环化成环而制得。其中,喹啉的合成方法主要是通过加热苯胺、甘油与硫酸及氧化剂(如硝基苯)反应,进而生成丙烯醛并与苯胺发生加成反应。利用各种苯胺衍生物和其他α,β-不饱和羰基化合物,则可以合成具有不同取代基的喹啉化合物,例如4-甲基喹啉(勒皮啶)便是由苯胺和甲基-乙烯基酮制得。
其他喹啉类化合物如2-甲基喹啉(喹哪啶)则通过邻氨基苯甲醛与丙酮缩合而合成。总的来说,喹啉及其同系物属于含氮杂双环芳烃类化合物,俗称重吡啶,并与吡啶一起统称为焦油碱,是高温煤焦油加工的产物。主要成分包括喹啉、异喹啉、甲基喹啉和二甲基喹啉等,集中在煤焦油的萘油馏分和洗油馏分中,含量约为0.3~0.5%。
这些化合物具有特殊的气味,并在暴露于空气或阳光下时逐渐变深。它们广泛应用于医药、染料、感光材料、橡胶、溶剂及化学试剂等领域。喹啉主要用于制造烟酸系、8-羟基喹啉系和奎宁系药物,如烟酸胺、强心剂、兴奋剂和治绦虫病药;8-羟基喹啉则用于制备治疗阿米巴虫病的药品、创伤消毒剂及防霉剂等。此外,伯氨奎宁、氯化奎宁和羟氨奎宁是合成的治疟疾特效药物。
异喹啉主要用于生产杀虫剂、抗疟药、橡胶硫化促进剂及测定稀有金属所需的化学试剂;甲基喹啉则用于制造彩色胶片增感剂和染料,并作为溶剂、浸渍剂和腐蚀抑制剂等。总体而言,这些化合物的应用范围广泛且重要。
中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
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2,6-二甲基喹啉 | 2,6-dimethylquinoline | 877-43-0 | C11H11N |
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2-间甲苯基喹啉 | 2-(m-tolyl)quinoline | 24641-30-3 | C16H13N |
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2-邻甲苯基喹啉-4-羧酸 | 2-(m-Tolyl)-chinolin-4-carbonsaeure | 20389-04-2 | C17H13NO2 |
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2-苯基喹啉-4-羧酸乙酯 | ethyl 2-phenylquinoline-4-carboxylate | 4420-46-6 | C18H15NO2 |
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2-苯基喹啉-4-甲醇 | (2-phenylquinolin-4-yl)methanol | 29268-33-5 | C16H13NO |
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2-苯基喹啉-3-醇 | 3-hydroxy-2-phenylquinoline | 5855-50-5 | C15H11NO |
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2-苯基喹啉-3-甲醛 | 2-phenylquinoline-3-carbaldehyde | 227803-21-6 | C16H11NO |
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2-苯基喹啉 | 2-Phenylquinoline | 612-96-4 | C15H11N |
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2-苯基-8-羟基喹啉 | 2-phenyl-8-hydroxyquinoline | 6961-25-7 | C15H11NO |
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2-苯基-8-甲基喹啉 | 8-methyl-2-phenylquinoline | 5353-90-2 | C16H13N |
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2-苯基-8-喹啉胺 | 2-phenylquinolin-8-amine | 116529-78-3 | C15H12N2 |
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2-苯基-7-羟基喹啉 | 7-hydroxy-2-phenylquinoline | 87741-95-5 | C15H11NO |
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2-苯基-7-喹啉胺 | 7-amino-2-phenylquinoline | 408508-52-1 | C15H12N2 |
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2-苯基-7-喹啉羧醛 | 2-phenylquinoline-7-carbaldehyde | 867162-43-4 | C16H11NO |
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2-苯基-6-羟基喹啉 | 2-phenylquinolin-6-ol | 87741-94-4 | C15H11NO |
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2-苯基-6-甲基喹啉 | 6-methyl-2-phenyl-quinoline | 27356-46-3 | C16H13N |
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2-苯基-6-溴喹啉 | 6-bromo-2-phenylquinoline | 3894-25-5 | C15H10BrN |
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2-苯基-6-氯喹啉 | 6-chloro-2-phenylquinoline | 60301-56-6 | C15H10ClN |
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2-苯基-6-喹啉胺 | 2-phenylquinolin-6-amine | 863770-87-0 | C15H12N2 |
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2-苯基-4-氨基喹啉 | 2-phenylquinolin-4-amine | 5855-52-7 | C15H12N2 |
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2-苯基-4-喹啉羧酸甲酯 | methyl 2-phenylquinoline-4-carboxylate | 4546-48-9 | C17H13NO2 |
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2-苯基-1H-喹啉-4-酮 | 2-phenyl-1H-quinolin-4-one | 14802-18-7 | C15H11NO |
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2-苯基-1,2,3,4-四氢异喹啉 | 2-phenyl-1,2,3,4-tetrahydroisoquinoline | 3340-78-1 | C15H15N |
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2-苯乙基异喹啉-2-鎓溴化物 | 2-phenethylisoquinolin-2-ium bromide | 10249-13-5 | Br*C17H16N |
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2-苄基异溴化喹啉 | 2-benzylisoquinolin-2-ium bromide | 23277-04-5 | Br*C16H14N |
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2-苄基异喹啉-1,3,4-三酮 | 2-benzylisoquinoline-1,3,4(2H)-trione | 21640-35-7 | C16H11NO3 |
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2-苄基喹啉 | 2-benzylquinoline | 1745-77-3 | C16H13N |
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2-胺喹啉-3-甲腈 | 2-aminoquinoline-3-carbonitrile | 31407-25-7 | C10H7N3 |
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2-肼基-4,8-二甲基喹啉 | 4,8-dimethyl-2-quinolyhydrazine | 57369-93-4 | C11H13N3 |
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2-肼喹啉 | 2-hydrazinoquinoline | 15793-77-8 | C9H9N3 |
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2-羟基喹啉-6-甲醛 | 2(1H)-quinolinone-6-carboxaldehyde | 90800-31-0 | C10H7NO2 |
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2-羟基喹啉-4-羧酸 | 2-quinolone-4-carboxylic acid | 15733-89-8 | C10H7NO3 |
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2-羟基喹啉-4-甲酰氯 | 2-hydroxyquinoline-4-carbonyl chloride | 57659-08-2 | C10H6ClNO2 |
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2-羟基喹啉-3-基硼酸 | (2-oxo-1,2-dihydroquinolin-3-yl)boronic acid | 1101864-58-7 | C9H8BNO3 |
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2-羟基-6-甲氧基喹啉 | 6-methoxy-2(1H)-quinolinone | 13676-00-1 | C10H9NO2 |
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2-羟基-4-甲基喹啉 | 4-methyl-1,2-dihydroquinolin-2-one | 607-66-9 | C10H9NO |
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2-羟基-3-甲基喹啉-4-酮 | 2-hydroxy-3-methyl-4H-quinolizinone-4-one | 15997-24-7 | C10H9NO2 |
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2-羟基-3-喹啉羧酸 | 2-oxo-1,2-dihydro-quinoline-3-carboxylic acid | 2003-79-4 | C10H7NO3 |
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2-碘喹啉 | 2-iodoquinoline | 6560-83-4 | C9H6IN |
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2-甲酰基苯并[h]喹啉 | 2-formylbenzo[h]quinoline | 904886-12-0 | C14H9NO |
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2-甲苯并[H]喹啉 | 2-methylbenzo[h]quinoline | 605-88-9 | C14H11N |
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2-甲磺酰基喹啉 | 2-(methylsulfonyl)quinoline | 17075-19-3 | C10H9NO2S |
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2-甲磺酰基-4-甲基喹啉 | 4-methyl-2-(methylsulfonyl)quinoline | 64495-40-5 | C11H11NO2S |
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2-甲氧基喹啉-8-胺 | 2-methoxyquinolin-8-amine | 134829-04-2 | C10H10N2O |
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2-甲氧基喹啉-4-羧酸 | 2-methoxyquinoline-4-carboxylic acid | 10222-62-5 | C11H9NO3 |
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2-甲氧基喹啉-3-硼酸 | (2-methoxyquinolin-3-yl)boronic acid | 886853-93-6 | C10H10BNO3 |
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2-甲氧基喹啉-3-甲醛 | 2-methoxyquinoline-3-carbaldehyde | 139549-06-7 | C11H9NO2 |
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2-甲氧基-喹啉-8-醇 | 2-methoxy-8-hydroxyquinoline | 74668-72-7 | C10H9NO2 |
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2-甲氧基-8-甲基喹啉 | 2-methoxy-8-methylquinoline | 885687-65-0 | C11H11NO |
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2-甲氧基-3-甲基喹啉 | 3-Methyl-2-methoxy-chinolin | 222317-28-4 | C11H11NO |
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