5,6,7,8-Tetrafluor-chinolin | 5280-07-9

• 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: 5,6,7,8-Tetrafluor-chinolin
• 英文别名: 5,6,7,8-Tetrafluoroquinoline
• CAS: 5280-07-9
• 化学式: C₉H₃F₄N
• 分子量: 201.123
• InChiKey: GBIKQULWCDDCAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6,7,8-Tetrafluor-chinolin 在 potassium amide 、 potassium permanganate 作用下， 以 氨 为溶剂， 反应 0.16h， 以17%的产率得到2-amino-5,6,7,8-tetrafluoroquinoline
  参考文献：
  名称：

  苯部分上多氟喹啉与液氨中的钠和钾酰胺的相互作用

  摘要：

  的5,6,7,8-四氟（相互作用1）和5,7,8-三氟-6-（三氟甲基）喹啉（2）用在液氨中进行作为亲核钠或氨基钾（NH 2 -）在吡啶环的2-位上加成，相应的加合物被氧化，得到相应的喹啉-2-胺。在1的情况下，酰胺的添加与6-和7-位的氨基脱氟同时进行。具有一个酰胺当量的5,6,8-（3），5,7,8-三氟喹啉（4）和5,7-二氟喹啉（5）经过两个邻位邻侧的C H键去质子化-氟原子以产生各自的长寿命喹啉基阴离子，其可以用作亲核合成子，例如其甲基化以产生各自的6-和7-甲基聚氟喹啉。当酰胺钾过量时，最初产生的喹啉基阴离子在2-或4-位上添加酰胺阴离子。

  DOI：

  10.1016/j.jfluchem.2012.01.007
• 作为产物：
  描述：

  2,3,4,5-tetrafluoroaniline 、 甘油 在 硫酸 、 sodium 3-nitrobenzenesulfonate 作用下， 反应 4.0h， 以75%的产率得到5,6,7,8-Tetrafluor-chinolin
  参考文献：
  名称：

  Effects of oligofluorine substitution on the mutagenicity of quinoline: a study with twelve fluoroquinoline derivatives

  摘要：

  A total of 12 variously fluorinated derivatives of quinoline (Q) were tested for their mutagenicity in Salmonella typhimurium TA100 in the presence of S9 mix to investigate the structure-mutagenicity relationship in oligofluorinated quinolines. Nine of them, 3,7-di-, 5,6-di-, 6,7-di-, 6,8-di-, 7,8-di-, 3,5,7-tri-, 5,6,8-tri-, 6,7,8-tri-, and 5,6,7,8-tetrafluoroquinolines (FQs), were newly synthesized for this purpose. Those fluorinated at position 3 were all non-mutagenic. Mutagenicity was enhanced by fluorine-substitution at position 5 or 7, but not in 3-FQs (i.e., 3,5-di-, 3,7-di-, and 3,5,7-triFQs). Some of the 6-fluorinated derivatives showed less maximum induced-revertants with more mutagenic potencies in terms of induced-revertants per dose than quinoline. No marked change occurred by fluorine-substitution at position 8. These results show that the effect of di- and trifluoro-substitution on mutagenicity is generally additive, while that of tetrafluorination approaches the deactivating effect of perfluorination. Our study suggests that 3-fluorine-substitution in the pyridine moiety may be a useful means of antimutagenic structural modification in pyridine-fused aromatic chemicals for medicinal and agricultural use. (C) 1999 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(98)00188-0

文献信息

• Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles
  作者：L. Yu. Safina、G. A. Selivanova、I. Yu. Bagryanskaya、V. D. Shteingarts

  DOI：10.1007/s11172-009-0134-z

  日期：2009.5

  contains three or four halogen atoms, their combined orientation effect outweighs the influence of the heterocycle N atom. It was found that the orientation of substitution in the reactions of 5,6,8-trifluoro- and 5,7,8-trifluoro-6-(trifluoromethyl)quinolines with piperidine depends on temperature, because the enthalpy control of the ratio of the rates of competing reactions changes to the entropy control

  在苯环（5,7-二氟-、5,7,8-三氟-、5,6,8-三氟-、8-氯-5,7-二氟-、5,6 ,7,8-四氟-和 5,7,8-三氟-6-（三氟甲基）喹啉）与以氮为中心的亲核试剂（氨水和液氨、水合肼、哌啶）反应进行了研究。如果氟化喹啉分子含有三个或四个卤素原子，它们的组合取向效应超过杂环N原子的影响。发现 5,6,8-trifluoro- 和 5,7,8-trifluoro-6-(trifluoromethyl)quinolines 与哌啶的反应中的取代取向取决于温度，因为控制的焓控制了 5,6,8-trifluoro- 和 5,7,8-trifluoro-6-(trifluoromethyl)quinolines 与哌啶的反应。竞争反应的速率改变了熵控制。
• Aromatic nucleophilic substitution: A case study of the interaction of a lithiated nitronyl nitroxide with polyfluorinated quinoline-N-oxides
  作者：Larisa Gurskaya、Tatyana Rybalova、Irina Beregovaya、Elena Zaytseva、Maxim Kazantsev、Evgeny Tretyakov

  DOI：10.1016/j.jfluchem.2020.109613

  日期：2020.9

  formation of products of aromatic nucleophilic substitution of the H atom at position 2 of the quinoline ring. The reaction regioselectivity is supported by the data of quantum-chemical calculations. Molecular and crystal structures of the obtained nitronyl nitroxides were solved by monocrystal X-ray diffraction analysis, and the nature of the radical was ascertained by electron spin resonance spectroscopy

  发现4,4,5,5-四甲基-4,5-二氢-1 H-咪唑-3-氧化物-1-氧基锂衍生物与5,6,7,8-四氟-或5,7反应，形成8-三氟-6-（三氟甲基）喹啉-N-氧化物，在喹啉环的2位上形成H原子的芳香亲核取代产物。反应区域选择性由量子化学计算的数据支持。通过单晶X射线衍射分析来解析所获得的亚硝酰基氮氧化物的分子和晶体结构，并且通过电子自旋共振光谱法确定自由基的性质。Cu（hfac）2的杂合物用合成的喹啉取代的亚硝酰基氮氧化物制备。根据X射线衍射分析，由于Cu原子同时配位了硝酰基和N-氧化物基团，在配合物中形成了七元金属环。
• Effects of oligofluorine substitution on the mutagenicity of quinoline: a study with twelve fluoroquinoline derivatives
  作者：Taka-aki Kato、Ken-ichi Saeki、Yutaka Kawazoe、Atsushi Hakura

  DOI：10.1016/s1383-5718(98)00188-0

  日期：1999.2

  A total of 12 variously fluorinated derivatives of quinoline (Q) were tested for their mutagenicity in Salmonella typhimurium TA100 in the presence of S9 mix to investigate the structure-mutagenicity relationship in oligofluorinated quinolines. Nine of them, 3,7-di-, 5,6-di-, 6,7-di-, 6,8-di-, 7,8-di-, 3,5,7-tri-, 5,6,8-tri-, 6,7,8-tri-, and 5,6,7,8-tetrafluoroquinolines (FQs), were newly synthesized for this purpose. Those fluorinated at position 3 were all non-mutagenic. Mutagenicity was enhanced by fluorine-substitution at position 5 or 7, but not in 3-FQs (i.e., 3,5-di-, 3,7-di-, and 3,5,7-triFQs). Some of the 6-fluorinated derivatives showed less maximum induced-revertants with more mutagenic potencies in terms of induced-revertants per dose than quinoline. No marked change occurred by fluorine-substitution at position 8. These results show that the effect of di- and trifluoro-substitution on mutagenicity is generally additive, while that of tetrafluorination approaches the deactivating effect of perfluorination. Our study suggests that 3-fluorine-substitution in the pyridine moiety may be a useful means of antimutagenic structural modification in pyridine-fused aromatic chemicals for medicinal and agricultural use. (C) 1999 Elsevier Science B.V. All rights reserved.
• Interaction of quinolines polyfluorinated on the benzene moiety with sodium and potassium amides in liquid ammonia
  作者：Larisa Yu. Gurskaya、Galina A. Selivanova、Vitalij D. Shteingarts

  DOI：10.1016/j.jfluchem.2012.01.007

  日期：2012.4

  The interaction of 5,6,7,8-tetrafluoro- (1) and 5,7,8-trifluoro-6-(trifluoromethyl)quinoline (2) with sodium or potassium amide in liquid ammonia proceeds as a nucleophile (NH2−) addition on the 2-position of the pyridine ring, the respective adducts being oxidized to give the respective quinoline-2-amines. In the case of 1 the amide addition is concurrent with aminodefluorination on the 6- and 7-positions

  的5,6,7,8-四氟（相互作用1）和5,7,8-三氟-6-（三氟甲基）喹啉（2）用在液氨中进行作为亲核钠或氨基钾（NH 2 -）在吡啶环的2-位上加成，相应的加合物被氧化，得到相应的喹啉-2-胺。在1的情况下，酰胺的添加与6-和7-位的氨基脱氟同时进行。具有一个酰胺当量的5,6,8-（3），5,7,8-三氟喹啉（4）和5,7-二氟喹啉（5）经过两个邻位邻侧的C H键去质子化-氟原子以产生各自的长寿命喹啉基阴离子，其可以用作亲核合成子，例如其甲基化以产生各自的6-和7-甲基聚氟喹啉。当酰胺钾过量时，最初产生的喹啉基阴离子在2-或4-位上添加酰胺阴离子。