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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4-氯-7-氟喹啉 | 4-chloro-7-fluoroquinoline | 391-82-2 | C9H5ClFN |
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4-氯-7-氟-6-硝基喹唑啉 | 4-chloro-7-fluoro-6-nitroquinazoline | 162012-70-6 | C8H3ClFN3O2 |
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4-氯-7-氟-6-甲氧基喹啉 | 4-chloro-7-fluoro-6-methoxyquinoline | 25759-94-8 | C10H7ClFNO |
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4-氯-7-氟-2-甲基喹啉 | 7-Fluor-4-chlor-2-methyl-chinolin | 18529-04-9 | C10H7ClFN |
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4-氯-7-三氟甲基喹啉-3-羧酸乙酯 | ethyl 4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate | 21168-42-3 | C13H9ClF3NO2 |
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4-氯-7-三氟甲基喹啉 | 4-chloro-7-trifluoromethyl quinoline | 346-55-4 | C10H5ClF3N |
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4-氯-7-(3-氯丙氧基)-3-氰基-6-甲氧基喹啉 | 7-(3-chloro-propoxy)-4-chloro-6-methoxy-quinoline-3-carbonitrile | 214470-68-5 | C14H12Cl2N2O2 |
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4-氯-7,8-二甲氧基喹啉 | 4-chloro-7,8-dimethoxyquinoline | 99878-79-2 | C11H10ClNO2 |
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4-氯-7,8-二甲基喹啉 | 4-Chloro-7,8-dimethylquinoline | 181950-53-8 | C11H10ClN |
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4-氯-6-硝基喹啉-3-羧酸乙酯 | Ethyl 4-chloro-6-nitro-quinoline-3-carboxylate | 103514-54-1 | C12H9ClN2O4 |
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4-氯-6-硝基喹啉 | 4-chloro-6-nitroquinoline | 13675-94-0 | C9H5ClN2O2 |
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4-氯-6-甲氧基喹啉 | 4-chloro-6-methoxyquinoline | 4295-04-9 | C10H8ClNO |
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4-氯-6-甲氧基-7-[3-(4-吗啉)丙氧基]喹唑啉 | 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline | 196195-13-8 | C16H20ClN3O3 |
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4-氯-6-甲氧基-7-(苯基甲氧基)-3-喹啉甲腈 | 7-benzyloxy-4-chloro-6-methoxyquinoline-3-carbonitrile | 214476-99-0 | C18H13ClN2O2 |
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4-氯-6-甲基喹啉 | 4-chloro-6-methylquinoline | 18436-71-0 | C10H8ClN |
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4-氯-6-甲基-喹啉-3-甲腈 | 4-Chloro-6-methylquinoline-3-carbonitrile | 1016818-79-3 | C11H7ClN2 |
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4-氯-6-甲基-8-苯基喹啉 | 8-chloro-5-methyl-2-phenylquinoline | 18618-02-5 | C16H12ClN |
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4-氯-6-氰基喹啉 | 4-chloroquinoline-6-carbonitrile | 219763-83-4 | C10H5ClN2 |
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4-氯-6-氨基喹啉 | 4-chloroquinolin-6-amine | 1085192-91-1 | C9H7ClN2 |
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4-氯-6-氟喹啉-3-羧酸 | 4-chloro-6-fluoroquinoline-3-carboxylic acid | 179024-67-0 | C10H5ClFNO2 |
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4-氯-6-氟喹啉 | 4-Chloro-6-fluoroquinoline | 391-77-5 | C9H5ClFN |
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4-氯-6-氟-3-硝基喹啉 | 4-chloro-6-fluoro-3-nitroquinoline | 99010-07-8 | C9H4ClFN2O2 |
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4-氯-6-氟-2-甲基喹啉 | 4-chloro-6-fluoro-2-methylquinoline | 18529-01-6 | C10H7ClFN |
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4-氯-6-氟-1,7-萘啶-3-甲腈 | 4-chloro-6-fluoro-[1,7]naphthyridine-3-carbonitrile | 305371-18-0 | C9H3ClFN3 |
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4-氯-6-乙氧基喹啉 | 4-Chlor-6-ethoxychinolin | 103862-63-1 | C11H10ClNO |
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4-氯-6-乙基喹啉 | 4-chloro-6-ethylquinoline | 188758-77-2 | C11H10ClN |
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4-氯-6-乙基-2-甲基喹啉 | 4-chloro-6-ethyl-2-methylquinoline | 123638-09-5 | C12H12ClN |
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4-氯-6-(三氟甲基)喹啉 | 4-chloro-6-(trifluoromethyl)quinoline | 49713-56-6 | C10H5ClF3N |
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4-氯-6,8-二甲基喹啉 | 4-chloro-6,8-dimethylquinoline | 196803-72-2 | C11H10ClN |
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4-氯-6,8-二氯喹啉 | 4,6,8-trichloro-quinoline | 855763-15-4 | C9H4Cl3N |
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4-氯-6,8-二氟喹啉 | 4-chloro-6,8-difluoroquinoline | 239463-89-9 | C9H4ClF2N |
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4-氯-6,7-二氯喹啉 | 4,6,7-trichloroquinoline | 855763-18-7 | C9H4Cl3N |
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4-氯-6,7-二氟喹啉 | 4-chloro-6,7-difluoro-quinoline | 863785-94-8 | C9H4ClF2N |
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4-氯-6,7-二亚甲基二羟喹唑啉 | 4-chloro-7,8-dihydro[1,4]dioxino[2,3-g]quinazoline | 52791-05-6 | C10H7ClN2O2 |
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4-氯-5-甲基喹啉 | 4-chloro-5-methylquinoline | 143946-48-9 | C10H8ClN |
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4-氯-5-氰基喹啉 | 4-chloro-quinoline-5-carbonitrile | 132586-14-2 | C10H5ClN2 |
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4-氯-5-氟喹啉盐酸盐 | 4-Chloro-5-fluoroquinazoline hydrochloride | 524955-72-4 | C8H5Cl2FN2 |
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4-氯-5-氟喹啉 | 4-chloro-5-fluoro-quinoline | 1229037-03-9 | C9H5ClFN |
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4-氯-5,8-二甲基喹啉 | 4-chloro-5,8-dimethyl-quinoline | 188759-77-5 | C11H10ClN |
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4-氯-5,7-二甲基喹啉 | 4-chloro-5,7-dimethyl-quinoline | 352205-97-1 | C11H10ClN |
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4-氯-3-苯基喹啉 | 4-chloro-3-phenylquinoline | 6319-32-0 | C15H10ClN |
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4-氯-3-碘喹啉 | 4-chloro-3-iodoquinoline | 590371-90-7 | C9H5ClIN |
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4-氯-3-硝基喹啉 | 4-chloro-3-nitroquinoline | 39061-97-7 | C9H5ClN2O2 |
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4-氯-3-喹啉磺酰氯 | 4-chloro-3-quinolinesulfonyl chloride | 157494-40-1 | C9H5Cl2NO2S |
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4-氯-3-喹啉甲醛 | 4-chloroquinoline-3-carbaldehyde | 201420-30-6 | C10H6ClNO |
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4-氯-2-苯基喹啉 | 4-chloro-2-phenylquinoline | 4979-79-7 | C15H10ClN |
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4-氯-2-甲氧基喹啉 | 2-methoxy-4-chloroquinoline | 4295-05-0 | C10H8ClNO |
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4-氯-2-甲基喹啉盐酸盐 | 4-chloro-2-methylquinoline hydrochloride | 83260-96-2 | C10H8ClN*ClH |
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4-氯-2-氰基喹啉 | 4-chloroquinoline-2-carbonitrile | 4552-43-6 | C10H5ClN2 |
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4-氯-2-三氯甲基喹啉 | 4-chloro-2-(trichloromethyl)quinoline | 35871-17-1 | C10H5Cl4N |
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