CAS: 73568-25-9; 2-Chloroquinoline-3-Carbaldehyde

该化合物是一种多用途有机化合物,具有重要的合成用途,是合成各种药品和农用化学品的关键中间体,具有独特的反应性和稳定性组合,有利于有机合成的有效转化,其具体结构特征使它成为开发具有多种生物活动的新化合物的有吸引力的构件.

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欧盟法规

ECHA物质C&L通报

上下游产品

CAS号68-12-2 N,N-二甲基甲酰胺 | CAS号103-84-4 N-乙酰苯胺 | CAS号612-62-4 2-氯喹啉 | CAS号93299-49-1 2-氯-3-喹啉甲醛肟 | CAS号613-91-2 苯乙酮肟 | CAS号125917-60-4 2-氯-3-喹啉甲醇 | CAS号1972-28-7 偶氮二甲酸二乙酯 | CAS号862249-68-1 2-chloro-3-lith... | CAS号111877-76-0 3-(1,3-dioxolan... | CAS号106835-44-3 1H-吡唑并[3,4-b]喹啉-3-胺 | CAS号104827-37-4 [(2-chloroquino... | CAS号91301-03-0 2-羟基喹啉-3-甲醛 | CAS号335672-04-3 3-(5-methyl-1H-... | CAS号83520-73-4 3-(1H-Benzimida... | CAS号95104-21-5 2-氯喹啉-3-甲腈 | CAS号36926-82-6 2-氧代-1,2-二氢喹啉-3-腈 | CAS号7689-03-4 喜树碱 | CAS号292077-58-8 1-(2-溴喹啉-3-基 )甲胺

合成工艺路线路线简述

  • 合成目标产物 2-Chloroquinoline-3-Carbaldehyde 主要起始原料 2-Chloroquinoline
  • (文献来源)合成步骤主要原料 2-Chloroquinoline
N-乙酰苯胺置于三氯氧磷体系中,用 N,N-二甲基甲酰胺 作为反应溶剂,化学反应生成 2-氯-3-喹啉甲醛
参考文献:Synthesis Of New Biphenyl-Substituted Quinoline Derivatives,Preliminary Screening And Docking Studies
标题:Synthesis Of New Biphenyl-Substituted Quinoline Derivatives,Preliminary Screening And Docking Studies
摘要:合成了含有联苯环的新喹啉衍生物,并通过红外光谱,1H NMR 和质谱研究对其进行了表征.对合成的化合物进行了抗菌,驱虫活性以及清除 Dpph 自由基特性的筛选.最低抑菌浓度值显示出了非常好的抑菌活性,属于强效生物制剂.这些化合物对 β-微管蛋白的结合能最小.化合物 11A,11C,13C 和 13D 对活性口袋有很好的亲和性,可以被认为是一种很好的β-微管蛋白抑制剂.
DOI:10.1007/s12039-013-0541-4

海关参考信息

专利信息


专利号:US-5212317-A
优先权日:1990-12-20
标 题:Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs
发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
权利人:UNIV NORTH CAROLINA STATE
摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a moiety of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

专利号:US-5258516-A
优先权日:1990-12-20
标题 :Optically pure D,E ring intermediates useful for the synthesis of camptothecin and camptothecin analogs
发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
权利人:NC STATE UNIVERSITY
摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 ; tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

专利号:US-5254690-A
优先权日:1990-12-20
标 题 :Alkoxymethylpyridine d-ring intermediates useful for the synthesis of camptpthecin and camptothecin analogs
发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
权利人:UNIV NORTH CAROLINA STATE
摘要:Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R 1 may be H, loweralkyl, loweralkoxy, or halo; R 2 , R 3 , R 4 , and R 5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluoromethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediates employed in these processes.

专利号:US-5264579-A
优先权日:1990-12-20
标 题 :D ring intermediates for the synthesis of camptothecin and camptothecin analogs
发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
权利人:UNIV NORTH CAROLINA STATE
摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, and Y is H, F or Cl, are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

专利号:US-5315007-A
优先权日:1990-12-20
标 题:Process for making DE ring intermediates for the synthesis of camptothecin and camptothecin analogs
发明人:COMINS DANIEL L; BAEVSKY MATTHEW F
权利人:UNIV NORTH CAROLINA STATE
摘要:Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R 6 is lower alkyl, R 7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R 8 is a compound of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R 11 is C 1 -C 4 alkyl and R 12 is the same as R 11 , or R 11 and R 12 together form cyclopentane or cyclohexane, and R 13 is: n (a) phenyl substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl, or n (b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C 3 -C 7 secondary alkyl or C 4 -C 7 tertiary alkyl groups, n R 10 is C 6 -C 10 alkyl, aryl or alkyl aryl, n and Y is H, F or Cl, n are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.

专利号:US-7074932-B2
优先权日:1999-06-24
标题 :Preparation of quinoline-substituted carbonate and carbamate derivatives
发明人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J
权利人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J
摘要:The invention relates to a process for preparing quinoline-substituted carbonate and carbamate compounds, which are important intermediates in the synthesis of 6-O-substituted macrolide antibiotics. The process employs metal-catalyzed coupling reactions to provide a carbonate or carbamate of formula (I) or (II) or a substrate that can be reduced to obtain the same.
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合成参考文献


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摘要:Silva, V. L. M.; Pinto, D. C. G. A.; Santos, C. M. M.; Rocha, D. H. A., Science of Synthesis Knowledge Updates, (2022) 3, 377.
摘要:Beier, P., Science of Synthesis Knowledge Updates, (2014) 2, 320.
摘要:Littke, A., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2012) 1, 210.
摘要:Arévalo, M. J.; Lavilla, R., Science of Synthesis: Multicomponent Reactions, (2013) 1, 311.
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