N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine | 260444-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine
• 英文别名: N,N-dimethyl-3-trifluoroacetylquinolin-4-amine；3-trifluoroacetyl-4-dimethylaminoquinoline；4-dimethylamino-3-trifluoroacetylquinoline；1-(4-(Dimethylamino)quinolin-3-YL)-2,2,2-trifluoroethanone；1-[4-(dimethylamino)quinolin-3-yl]-2,2,2-trifluoroethanone
• CAS: 260444-63-1
• 化学式: C₁₃H₁₁F₃N₂O
• 分子量: 268.238
• InChiKey: CQMXHKHMIJUJSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine 在 盐酸羟胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以88%的产率得到3-trifluoromethylisoxazolo[4,3-c]quinoline
  参考文献：
  名称：

  Facile and Convenient Syntheses for Fluorine-Containing Pyrazolo[4,3-c]quinolines, Isoxazoloquinolines, and 1,4-Diazepino[6,5-c]quinolines

  摘要：

  N,N-Dimethyl-3-trifluoroacetyl-4-quinolylamine underwent an aromatic nucleophilic N-N exchange reaction with hydrazines followed by cyclocondensation to afford the corresponding novel fluorine-containing 1H- and 2H-pyrazolo[4,3-c]quinolines in good to high yields. This reaction could be extended to the synthesis of novel CF3-containing isoxazoloquinolines using hydroxylamine. Furthermore, the use of 1,2-ethylenediamine and 1,2-phenylenediamines gave the corresponding fluorine-containing 1,4-diazepino[6,5-c]quinoline derivatives in high yields.

  DOI：

  10.3987/com-14-s(k)76
• 作为产物：
  描述：

  二甲基-喹啉-4-基-胺 、 4-二甲氨基-1-三氟乙酰基吡啶三氟乙酸盐 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以87%的产率得到N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine
  参考文献：
  名称：

  在4-氨基喹啉的侧链中引入3-（2,2,2-三氟乙基）-γ-羟基-γ-内酰胺基。合成与抗疟活动

  摘要：

  在本文中，我们报告了衍生自4-氨基喹啉的两种系列氟烷基化γ-内酰胺类化合物的合成及抗疟疾特性，它们是用于治疗疟疾的有效化学治疗剂。通过分几步获得的这些分子导致鉴定出非常有效的结构，具有体外活性，可对19-50 nM范围内的可变敏感性（3D7和W2）恶性疟原虫克隆产生抗性，抗性指数在1.0-2.5范围内。此外，所选择的分子（50，51，58，60，63，70，72，74，78，81，84，和87）代表这两个系列的化合物，当针对浓度高达100μM的人脐静脉内皮细胞进行体外测试时，在体外未显示细胞毒性。最有前途的化合物（82和84）对氯喹敏感菌株3D7的IC 50值接近26和19 nM，对耐多药菌株W2的IC 50值接近49和42 nM。此外，发现两种模型化合物（50和70）在pH 7.4和5.2下可在48小时内保持稳定。总体而言，我们的初步数据表明此类结构包含有希望进一步研究的候选对象。

  DOI：

  10.1021/jm301076q

文献信息

• A Simple Synthetic Method for 3-Trifluoroacetylated 4-Aminoquinolines from 4-Dimethylaminoquinoline by Novel Trifluoroacetylation and N-N Exchange Reactions
  作者：Etsuji Okada、Takushi Sakaemura、Naofumi Shimomura

  DOI：10.1246/cl.2000.50

  日期：2000.1

  Acylation of 4-dimethylaminoquinoline with 1-trifluoroacetyl-4-dimethylaminopyridinium trifluoroacetate proceeded cleanly to give 3-trifluoroacetyl-4-dimethylaminoquinoline, which underwent nucleophilic aromatic substitutions with various amines to afford the corresponding N-N exchanged 3-trifluoroacetyl-4-aminoquinolines in excellent yields.

  4-二甲基氨基喹啉与 1-三氟乙酰基-4-二甲基氨基吡啶鎓三氟乙酸盐的酰化反应顺利进行，得到 3-三氟乙酰基-4-二甲基氨基喹啉，其与各种胺进行亲核芳香取代，以优异的产率得到相应的 NN 交换的 3-三氟乙酰基-4-氨基喹啉.
• Efficient Syntheses of Fluorine-Containing Pyrimido[5,4-c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reactions of 3-Trifluoro-acetylquinolin-4-amine with Aldehydes and Ketones
  作者：Etsuji Okada、Mizuki Hatakenaka、Shiro Nakano、Takushi Sakaemura、Takashi Mori、Terukazu Terauchi

  DOI：10.3987/com-14-13070

  日期：——

  3-Trifluoroacetylquinolin-4-amine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes under almost the same conditions, mostly gave benzo[h][1,6]naphthyridine derivatives in excellent combined yields.
• Copper catalyzed 1,3-dipolar cycloaddition reaction of azides with N-(2-trifluoroacetylaryl)propargylamines
  作者：Jean-Florent Lamarque、Christophe Lamarque、Sandrine Lassara、Maurice Médebielle、Jérome Molette、Emilie David、Stéphane Pellet-Rostaing、Marc Lemaire、Etsuji Okada、Dai Shibata、Guillaume Pilet

  DOI：10.1016/j.jfluchem.2008.05.015

  日期：2008.9

  The synthesis of N-(2-trifluoroacetylaryl)propargylamines 10-14 and 17 is presented. The copper(I) catalyzed cycloaddition reaction of these propargylamines (dipolarophiles) with a series of azides (1,3-dipoles) 18-20, 21 and 24 was found to proceed smoothly in dimethylsulfoxide at room temperature, to furnish the corresponding 1,4-disubstituted-[1,2,3]triazole derivatives 26-36 in moderate to good yields. (c) 2008 Elsevier B.V. All rights reserved.
• SIMPLE SYNTHESES OF 3-TRIFLUOROACETYL-4-QUINOLYLAMINES, SULFIDES, AND ETHERS STARTING FROM N,N-DIMETHYL-4-QUINOLYLAMINE
  作者：Etsuji Okada、Mizuki Hatakenaka、Takushi Sakaemura、Naofumi Shimomura、Takuro Ashida

  DOI：10.3987/com-12-s(n)73

  日期：——

  New 3-trifluoroacetyl-4-quinolylamines (2), sulfides (3), and ethers (4) were synthesized in good to high yields by aromatic nucleophilic substitution reactions of N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine (1), which was easily prepared by acylation of N,N-dimethyl-4-quinolylamine with 1-trifluoroacetyl-4-dimethylaminopyridinium trifluoroacetate, with amines, thiols, alcohols, and phenols.
• A Facile and Convenient Synthetic Method for Fluorine-Containing Dibenzo[b,h][1,6]naphthyridines, Thiochromeno[3,2-c]quinolines, and Chromeno[3,2-c]quinolines
  作者：Etsuji Okada、Mizuki Hatakenaka、Masayuki Kuratani、Takashi Mori、Takuro Ashida

  DOI：10.3987/com-13-s(s)57

  日期：——

  Novel fluorine-containing dibenzo[b,h][1,6]naphthyridines (3), thiochromeno[3,2-c]quinolines (5), and chromeno[3,2-c]quinolines (7) were synthesized in moderate to high yields by the trifluoromethanesulfonic acid catalyzed cyclization of N-aryl-3-trifluoroacetyl-4-quinolylamines (2) and aryl 3-trifluoroacetyl-4-quinolyl sulfides (4) and ethers (6), easily prepared by aromatic nucleophilic substitution reactions of N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine (1) with p-substituted anilines, thiophenols, and phenols, respectively.