喹啉类化合物
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 |
|---|---|---|---|---|
| —— | 2,6,8-Trimethylquinoline-4-carboxylate | 93189-20-9 | C13H12NO2- |
|
| —— | 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride | 841275-84-1 | C10H9ClN2O4S |
|
| —— | 6,8-Dimethylquinoline hydrochloride | 1255574-45-8 | C11H12ClN |
|
| —— | 7-Bromoquinolin-3-amine dihydrochloride | 1266226-05-4 | C9H9BrCl2N2 |
|
| —— | 4,6-Dichloro-2-quinolinecarboxylic acid | 902742-67-0 | C10H5Cl2NO2 |
|
| —— | Carbostyril, monosodium salt | 4510-76-3 | C9H7NNaO2+ |
|
| —— | 6-Bromo-5-fluoroquinoline hydrochloride | 127827-51-4 | C9H6BrClFN |
|
| —— | Cinchonidine sulphate | 524-61-8 | C38H46N4O6S |
|
| —— | 6-chloro-4-methoxyquinolin-2-(1H)-one | 865817-83-0 | C10H8ClNO2 |
|
| —— | (R)-[(4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;dihydrochloride | 24302-67-8 | C19H24Cl2N2O |
|
| —— | (R)-[(2R,4S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride | 69257-04-1 | C26H29ClN2O |
|
| —— | 5-chloro-6-quinolinecarbaldehyde | 180421-64-1 | C10H6ClNO |
|
| —— | 4-Bromo-8-chloro-5-methoxyquinoline | 1189107-37-6 | C10H7BrClNO |
|
| —— | 4,7-Dibromo-6-methylquinoline | 1189107-21-8 | C10H7Br2N |
|
| —— | 4,6-Dibromo-2,8-dimethylquinoline | 1189107-47-8 | C11H9Br2N |
|
| —— | 4-Bromo-5,8-difluoroquinoline | 1189106-41-9 | C9H4BrF2N |
|
| —— | 4,8-Dibromo-2-phenylquinoline | 1189106-08-8 | C15H9Br2N |
|
| —— | 4,8-Dibromo-6-methylquinoline | 1189106-63-5 | C10H7Br2N |
|
| —— | 4,6-Dibromo-7-methylquinoline | 1189105-55-2 | C10H7Br2N |
|
| —— | 3-Bromo-6-fluoro-4-hydroxyquinoline | 1065087-77-5 | C9H5BrFNO |
|
| —— | 4,8-Dibromo-2,6-dimethylquinoline | 1189107-53-6 | C11H9Br2N |
|
| —— | 4-Amino-7,8-difluoroquinoline | 1189107-49-0 | C9H6F2N2 |
|
| —— | (8-Bromoquinolin-4-yl)methanol | 1190315-99-1 | C10H8BrNO |
|
| —— | 8-Bromoquinoline-4-carbonitrile | 1190315-89-9 | C10H5BrN2 |
|
| —— | (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;sulfuric acid;dihydrate | 524-61-8 | C19H28N2O7S |
|
| —— | 8-Bromo-5-fluoroquinolin-4-OL | 1065092-35-4 | C9H5BrFNO |
|
| —— | 4-bromoquinoline-7-carbonitrile | 1242063-18-8 | C10H5BrN2 |
|
| —— | 4-cyano-3-bromoquinoline | 1253790-93-0 | C10H5BrN2 |
|
| —— | Cinchonine dihydrochloride | 24302-67-8 | C19H24Cl2N2O |
|
| —— | (S)-[(2R,4R,5S)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;chloride | 69257-04-1 | C26H29ClN2O |
|
| —— | 4-Chloro-5-iodoquinoline | 143946-46-7 | C9H5ClIN |
|
| —— | 7-bromo-4-formylquinoline | 898404-22-3 | C10H6BrNO |
|
| —— | 4-Bromo-7,8-dimethylquinoline | 1070879-37-6 | C11H10BrN |
|
| —— | 4,8-Dimethylquinoline-3-carboxylic acid | 1031929-51-7 | C12H11NO2 |
|
| —— | 4,7-Dibromo-2-methylquinoline | 1070879-54-7 | C10H7Br2N |
|
| —— | 4-Bromo-5-chloro-8-methylquinoline | 1070879-41-2 | C10H7BrClN |
|
| —— | 4,6-dibromo-2-methylquinoline | 1070879-53-6 | C10H7Br2N |
|
| —— | 4-Bromo-6-ethylquinoline | 1070879-25-2 | C11H10BrN |
|
| —— | 4-Bromo-5,8-dichloroquinoline | 1070879-38-7 | C9H4BrCl2N |
|
| —— | 4-Bromo-7,8-dichloroquinoline | 1070879-40-1 | C9H4BrCl2N |
|
| —— | 4-Bromo-5,8-dimethylquinoline | 1070879-34-3 | C11H10BrN |
|
| —— | 4-Bromo-6,7-dichloroquinoline | 1070879-39-8 | C9H4BrCl2N |
|
| —— | copper;quinolin-8-ol | 13014-03-4 | 2C9H7NO*Cu |
|
| —— | 3-(Quinolin-6-YL)propan-1-amine | 465529-51-5 | C12H14N2 |
|
| —— | Cinchonine sulfate | 5949-16-6 | C38H46N4O6S |
|
| —— | methyl 8-hydroxyquinoline-4-carboxylate | 71294-66-1 | C11H9NO3 |
|
| —— | 6-(dimethylamino)-2H-chromen-2-one | 98786-08-4 | C11H11NO2 |
|
| —— | 3-amino-quinolin-4-ol; hydrochloride | 129377-66-8 | C9H8N2O*ClH |
|
| —— | (+/-)-<i>cis</i>-octahydro-isoquinolin-4a-ol; hydrochloride | 81562-78-9 | C9H17NO*ClH |
|
| —— | (1-Benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol;chloride | 77481-82-4 | C27H31ClN2O2 |
|
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