CAS: 347-42-2; 2-(Trifluoromethyl)Quinoline

该化合物是一种氟化环环环化合物,在2位置上以三氟甲基组替代了一条quinoline骨架,这种结构元素具有强化电子脱衣特性,提高了代谢稳定性,使其在制药和农用化学应用中具有价值.三氟甲基组有助于增加亲脂性和生物利用率,而quino核心则提供了多功能支架,供进一步发挥功能.该化合物通常用作生物活性分子合成的中间体,包括活性酶抑制剂和抗微生物剂.在各种反应条件下,其稳定性以及与交叉组合方法的兼容性进一步强调了其在药用化学和材料科学研究中的效用.

结构式图片

相似化合物

1075184-01-8 176722-64-8 176722-74-0

欧盟法规

ECHA物质C&L通报

上下游产品

1-trifluoromethyl-3-(phenylamino)prop-2-en-1-one aniline p-toluidinep-toluidine 1-phenylimino-3-phenoxy-3-trifluoromethylprop-2-ene 2-(trifluoromethyl)quinoline-4-carboxylic acid 2-trifluoromethyl-8-quinolinecarboxylic acid 2-trifluoromethyl-3-quinolinecarboxylic acid

合成工艺路线路线简述

    2-(三氟甲基)喹啉-4(1H)-酮置于正丁基锂,三溴氧磷体系中,用 四氢呋喃,正己烷 用作溶剂,化学反应 2.25H,反应生成2-三氟甲基喹啉
    参考文献:2-(三氟甲基)喹啉酮的选择性和高效结构制备
    标题:2-(三氟甲基)喹啉酮的选择性和高效结构制备
    摘要:苯胺与 Et 4,4,4-三氟乙酰乙酸酯之间的酸催化环化-缩合反应得到 1,4-二氢-2-三氟甲基-4H-4-喹啉酮,可轻松转化为 4-溴-2-(三氟甲基)喹啉.当用丁基锂处理时,它们进行卤素/金属交换,反应生成2-三氟甲基-4-喹啉基锂,和氢/金属交换,当用二异丙基氨基锂处理时反应生成4-溴-2-三氟甲基-3-喹啉基锂.后一种中间体的捕获提供了 3 官能化的产物,可以通过溴原子的亲电取代进一步加工.这些调查产生了一些意想不到的发现,最值得注意的是前所未有的支撑效应和违反直觉的卤素反应性.[在 Scifinder (R) 上]
    Doi:10.1002/ejoc.200390217

    海关参考信息

    专利信息


    专利号:US-7129357-B2
    优先权日:2003-09-15
    标题:Synthesis of quinoline 5-carboxamides useful for the preparation of PDE IV inhibitors
    发明人:ANDREWS DAVID R; TANG SUHAN; WU WENXUE; KALLINEY SAMI Y; SUDHAKAR ANANTHA; NIELSEN CHRISTOPHER
    权利人:SCHERING CORP
    摘要:In one embodiment, the present application discloses a process for making the compound of the formula:

    专利号:EP-1756029-B1
    优先权日:2004-04-08
    标 题:Novel compounds, the preparation and the use thereof for a regiospesific synthesis of perfluor(alkyl) group heterocycles
    发明人:EL KHARRAT SALEM; LAURENT PHILIPPE; BLANCOU HUBERT
    权利人:CENTRE NAT RECH SCIENT; UNIV MONTPELLIER II
    摘要:The invention relates to compounds of formula (1), wherein Z is a hydrogen or halogen atom; R'F is a perfluoroalkyl group CnF2n+1 in which n is an integer ranging from 1 to 12; R is in an ortho, meta or para position and represents an electron donor group, an electron attracting group, an aryl group or a heteroaryl group with the provision that R is an aryl or a heteroaryl. A method for preparing the inventive compounds (1) and a method for preparing heterocyclic compounds therefrom are also disclosed.

    专利号:US-6774125-B2
    优先权日:1998-06-22
    标 题:Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
    发明人:AUDIA JAMES E; THOMPSON RICHARD C; WILKIE STEPHEN C; BRITTON THOMAS C; PORTER WARREN J; HUFFMAN GEORGE W; LATIMER LEE H
    权利人:ELAN PHARM INC; LILLY CO ELI
    摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

    专利号:US-6509331-B1
    优先权日:1998-06-22
    标题:Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
    发明人:AUDIA JAMES E; THOMPSON RICHARD C; WILKIE STEPHEN C; BRITTON THOMAS C; PORTER WARREN J; HUFFMAN GEORGE W; LATIMER LEE H
    权利人:ELAN PHARM INC; LILLY CO ELI
    摘要:Disclosed are compounds which inhibit beta-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits beta-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

    专利号:US-6696438-B2
    优先权日:1998-06-22
    标题:Cyclic amino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
    发明人:AUDIA JAMES E; DRESSMAN BRUCE A; SHI QING
    权利人:ELAN PHARM INC; LILLY CO ELI
    摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

    专利号:US-7390801-B2
    优先权日:1996-12-23
    标题:Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
    发明人:THORSETT EUGENE D; PLEISS MICHAEL A; LATIMER LEE H; JOHN VARGHESE; FREEDMAN STEPHEN; BRITTON THOMAS C; AUDIA JAMES A; REEL JON K; DRESSMAN BRUCE A; DROSTE JAMES J; HENRY STEVEN S; STUCKY RUSSELL D; PORTER WARREN J
    权利人:ATHENA NEUROSCIENCES INC; LILLY CO ELI
    摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.
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    合成参考文献


    摘要:Ouyang, Y.; Shou, J.-Y.; Qing, F.-L., Science of Synthesis: Special Topics, (2022) 1, 276.
    参考文献:10.1007/978-1-4939-3112-5_3
    摘要:Dash-Wagh S, Langel Ü, Ulfendahl M. PepFect6 Mediated SiRNA Delivery into Organotypic Cultures. Methods Mol Biol. 2016;1364():27–35. doi: 10.1007/978-1-4939-3112-5_3.
    参考文献:10.1186/1475-2875-9-51
    摘要:Milner E, McCalmont W, Bhonsle J, Caridha D, Cobar J, Gardner S, Gerena L, Goodine D, Lanteri C, Melendez V, Roncal N, Sousa J, Wipf P, Dow GS. Anti-malarial activity of a non-piperidine library of next-generation quinoline methanols. Malaria Journal. 2010 Feb 11;9(1):51. doi: 10.1186/1475-2875-9-51.
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