6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinolin-7-ol | 1579275-08-3

• 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: 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinolin-7-ol
• CAS: 1579275-08-3
• 化学式: C₁₃H₉ClF₃NO
• 分子量: 287.669
• InChiKey: IDUHHMCBAGIGCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  33.12
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (±)-6-chloro-4-(cyclopropylethynyl)-7-hydroxy-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one 在 potassium nitrososulfonate 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 24.0h， 以10%的产率得到6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinolin-7-ol
  参考文献：
  名称：

  The phenolic metabolites of the anti-HIV drug efavirenz: Evidence for distinct reactivities upon oxidation with Frémy's salt

  摘要：

  Efavirenz (EFV) is a non-nucleoside reverse transcriptase inhibitor administered as first line treatment against HIV-1. The major drawbacks of EFV therapy are neurotoxicity and hepatotoxicity, which may result from bioactivation to reactive metabolites capable of reacting with bionucleophiles. We investigated the in vitro oxidation of the phenolic EFV metabolites, 7-hydroxy-efavirenz (7-OH-EFV) and 8hydroxy-efavirenz (8-OH-EFV), with Fremy's salt. A quinoline derivative, 6-chloro-2-cyclopropy1-4-(trifluoromethyl)quinolin-7-ol, presumably stemming from a radical rearrangement, was selectively obtained from 7-OH-EFV in 10% yield. In contrast, when subjected to the same oxidation conditions, 8-OH-EFV was considerably more prone to oxidative degradation and yielded multiple products. Among these, a quinone imine derivative was tentatively identified upon LC-ESI-MS/MS analysis of the reaction mixture. These observations demonstrate a remarkable difference in the reactivities of the two phenolic EFV metabolites under oxidative conditions. Moreover, taking into consideration the toxicological significance of quinone imine derivatives, these findings may explain earlier reports that 8-OH-EFV is a more potent toxicant than 7-OH-EFV in model test systems. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.022