2-trichloromethylquinoxaline | 172225-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-trichloromethylquinoxaline
• 英文别名: 2-(Trichloromethyl)quinoxaline
• CAS: 172225-52-4
• 化学式: C₉H₅Cl₃N₂
• 分子量: 247.511
• InChiKey: BEQYLCPTELFDLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯苯甲醛 、 2-trichloromethylquinoxaline 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到2-Chloro-2-(4-chloro-phenyl)-1-quinoxalin-2-yl-ethanone
  参考文献：
  名称：

  TDAE法氮杂杂环系列中α-氯酮的原始合成

  摘要：

  我们在这里报告了基于2-（三氯甲基）喹喔啉与芳族醛之间反应的TDAE策略的氮杂杂环系列中新的α-氯酮的原始和快速合成。该反应性已普遍化为喹啉三氯化物。

  DOI：

  10.1016/j.tetlet.2006.07.030
• 作为产物：
  描述：

  2-甲基喹喔啉 在 五氯化磷 、 三氯氧磷 作用下， 以84%的产率得到2-trichloromethylquinoxaline
  参考文献：
  名称：

  TDAE法氮杂杂环系列中α-氯酮的原始合成

  摘要：

  我们在这里报告了基于2-（三氯甲基）喹喔啉与芳族醛之间反应的TDAE策略的氮杂杂环系列中新的α-氯酮的原始和快速合成。该反应性已普遍化为喹啉三氯化物。

  DOI：

  10.1016/j.tetlet.2006.07.030

文献信息

• Facile Synthesis of 6-Trichloromethylpterin and 2-Chloro-3-trichloromethylquinoxaline along with a Library of Trichloromethyl Heterocycles Using<i>N</i>-Chlorosuccinimide and Triphenyl Phosphine
  作者：Shyamaprosad Goswami、Annada C. Maity、Hoong-Kun Fun

  DOI：10.1246/cl.2007.552

  日期：2007.4.5

  A general synthesis of 6-trichloromethylpterin, 2-chloro-3-trichloromethylquinoxaline and 2-amino-7-trichloromethyl-1,8-naphthyridine along with a series of trichloromethyl heterocycles (1–11) has been reported in one-pot mild neutral condition in good yield. This method is compared with the usual method using phosphorus pentachloride in phosphorus oxychloride.

  在一锅中温和中性条件下，以良好的产率合成了6-三氯甲基蝶啶、2-氯-3-三氯甲基喹喉和2-氨基-7-三氯甲基-1,8-萘啶等一系列三氯甲基杂环化合物（1-11）。该方法与通常使用五氯化磷的磷酰氯方法进行了比较。
• FLUORINATING AGENT, PROCESS FOR PRODUCING THE SAME, AND USE THEREOF
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1072576A1

  公开（公告）日：2001-01-31

  The invention disclose a hydrogen fluoride containing composition comprising hydrogen fluoride and a compound which is liquid in the standard state (25 °C, 1 atmosphere) and has a boiling point of 120 °C or more and pka of 12 or more at 25 °C, and use of the composition for a fluorination agent. The compound which can be preferably used is represented by the formula (1): wherein R1 to R4 are a substituted or unsubstituted alkyl or aryl group and can be the same or different, and R1 or R2 or R3 and R4 can bond to form a ring having a nitrogen atom or a nitrogen atom and other hetero atom, or R1 and R3 can bond to form a ring having a nitrogen atom or a nitrogen atom and other hetero atom. The fluorination agent of the invention exerts effect with a similar reaction mechanism to hydrogen fluoride, can be applied to the halogen exchange reaction of a halogen containing organic compound, and can produce a fluorine containing compound with safety and ease without specific equipment or technique.

  本发明公开了一种含氟化氢的组合物，该组合物包括氟化氢和一种在标准状态（25℃，1 个大气压）下为液态、沸点为 120℃或以上、25℃时 pka 为 12 或以上的化合物，以及该组合物在氟化剂中的用途。 可优先使用的化合物由式（1）表示： 其中 R1 至 R4 是取代或未取代的烷基或芳基，可以相同或不同，R1 或 R2 或 R3 和 R4 可以键合形成具有氮原子或氮原子和其他杂原子的环，或 R1 和 R3 可以键合形成具有氮原子或氮原子和其他杂原子的环。 本发明的氟化剂与氟化氢的反应机理相似，可用于含卤有机化合物的卤素交换反应，无需特定的设备或技术，即可安全、方便地生产出含氟化合物。
• Highly efficient microwave assisted α-trichlorination reaction of α-methylated nitrogen containing heterocycles
  作者：Pierre Verhaeghe、Pascal Rathelot、Armand Gellis、Sylvain Rault、Patrice Vanelle

  DOI：10.1016/j.tet.2006.05.081

  日期：2006.8

  A new methodology permitting the chlorination of different alpha-methylated nitrogen containing heterocycles into N-alpha-trichloromethylated derivatives is described here. The combination of microwave technology with a PCl5/POCl3 protocol has allowed to reach trichloromethyl derivatives with high yields in a few minutes. (c) 2006 Elsevier Ltd. All rights reserved.
• Cartwright, David; Ferguson, John R.; Giannopoulos, Thomas, Journal of the Chemical Society. Perkin transactions I, 1995, # 20, p. 2595 - 2598
  作者：Cartwright, David、Ferguson, John R.、Giannopoulos, Thomas、Varvounis, George、Wakefield, Basil J.

  DOI：——

  日期：——
• Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-a]quinoxalines as new antiplasmodial agents
  作者：Nicolas Primas、Peggy Suzanne、Pierre Verhaeghe、Sébastien Hutter、Charline Kieffer、Michèle Laget、Anita Cohen、Julie Broggi、Jean-Charles Lancelot、Aurélien Lesnard、Patrick Dallemagne、Pascal Rathelot、Sylvain Rault、Patrice Vanelle、Nadine Azas

  DOI：10.1016/j.ejmech.2014.06.014

  日期：2014.8

  Thanks to a preliminary in vitro screening of several CCl3-substituted-nitrogen containing heterocycles belonging to our chemical library, the 2-trichloromethylquinoxaline scaffold appeared to be of potential interest for developing new antiplasmodial agents. Then, combining these experimental results to the antimalarial properties reported for various pyrrolo[1,2-a]quinoxaline derivatives, an original series of fifteen 7-substituted-4-trichoromethylpyrrolo[1,2-a]quinoxalines was synthesized in a 4 to 5 reaction steps pathway. All molecules were evaluated in vitro toward both their antiplasmodial activity on the K1 multi-resistant Plasmodium falciparum strain and their cytotoxicity on the HepG2 human cell line. Thus, 3 hit molecules were identified, displaying IC50 values in the micromolar range and low cytotoxicity values, reaching good selectivity indexes, in comparison with the reference drugs chloroquine and doxycycline. Structure-activity relationship studies showed that the pyrrolo[1,2-a]quinoxaline scaffold can support selective antiplasmodial activity when substituted at position 4 by a CCl3 group. However, substitution at position 7 of the same scaffold is neither beneficial for cytotoxicity nor favourable for the solubility in the biological media.