N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine | 221636-61-9

• 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-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine
• 英文别名: Pgxppoluvsrrbi-uhfffaoysa-；2,2,2-trifluoro-1-[8-(prop-2-ynylamino)-7-(2,2,2-trifluoroacetyl)quinolin-5-yl]ethanone
• CAS: 221636-61-9
• 化学式: C₁₆H₈F₆N₂O₂
• 分子量: 374.242
• InChiKey: PGXPPOLUVSRRBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine 在 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 生成 1-(8-dimethylaminomethyl-7-trifluoromethyl[1,10]phenanthrolin-5-yl)-2,2,2-trifluoroethane-1,1-diol
  参考文献：
  名称：

  Fluorine-containing 1,10-phenanthrolines synthesis: an original and efficient approach by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with various nucleophiles

  摘要：

  Novel fluorine-containing 1,10-phenanthrolines having a variety of substituents at the 3-position were easily synthesized in moderate yields by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with various amines, thiols, and phenols. Unexpectedly. the reactive intermediates 1,4-dihydro-1,10-phenanthrolin-4-ols were isolated for the first time in the reactions with dialkylamines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.047
• 作为产物：
  描述：

  N,N-二甲基-8-喹啉胺 在 吡啶 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 26.0h， 生成 N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine
  参考文献：
  名称：

  Aromatic Nucleophilic N-N, N-S and N-O Exchange Reactions: Efficient Synthesis of 5,7-Bis(trifluoroacetyl)-8-quinolylamines, Sulfides and Ethers

  摘要：

  通过 N,N-二甲基-5,7-双(三氟乙酰基)-8-喹啉胺与胺、硫醇和醇的芳香族亲核 N-N、N-S 和 N-O 交换反应，合成了各种 5,7-双(三氟乙酰基)-8-喹啉胺、硫化物和醚，产量极高。在碱催化下，生成的 8-喹啉基苄基硫醚发生环化反应，随后脱水，得到高产率的含氟噻吩并[3,2-h]喹啉类化合物。

  DOI：

  10.1055/s-2000-6243

文献信息

• 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.
• Okada, Etsuji; Tsukushi, Norikado, Synlett, 1999, # 2, p. 210 - 212
  作者：Okada, Etsuji、Tsukushi, Norikado

  DOI：——

  日期：——
• Facile synthesis of fluorine-containing 1,10-phenanthrolines by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with amines: isolation of the intermediates 1,4-dihydro-1,10-phenanthrolin-4-ols
  作者：Dai Shibata、Etsuji Okada、Jérôme Molette、Maurice Médebielle

  DOI：10.1016/j.tetlet.2008.09.172

  日期：2008.12

  Novel fluorine-containing 1,10-phenanthrolines having dialkyl-, alkyl, and arylaminomethyl substituents at the 3-position were easily synthesized in moderate yields by the pyridine-ring formation reaction of N-propargyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with various a mines. Unexpectedly, the reactive intermediates 1,4-dihydro-1,10-phenanthrolin-4-ols were isolated for the first time in the reactions with dialkylamines. (C) 2008 Elsevier Ltd. All rights reserved.