6-fluoro-4-methylquinoline | 31598-65-9

• 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: 6-fluoro-4-methylquinoline
• CAS: 31598-65-9
• 化学式: C₁₀H₈FN
• mdl: MFCD18803097
• 分子量: 161.179
• InChiKey: BGTFVZDPIQRVRY-UHFFFAOYSA-N

物化性质

• 沸点：
  261.5±20.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  6-fluoro-4-methylquinoline 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 40.0h， 以79%的产率得到6-fluoro-4-methylquinoline N-oxide
  参考文献：
  名称：

  Anti-mutagenic structural modification by fluorine-substitution in highly mutagenic 4-methylquinoline derivatives

  摘要：

  We have previously shown that fluorine-substitution at position 3 of quinoline deprived this molecule of mutagenicity, possibly due to interference with the yield of its metabolically activated form, the 1,4-hydrated 2,3-epoxide (enamine epoxide), which is directly responsible for the mutagenic modification of DNA. To further explore the possibility of a method for anti-mutagenic modification of mutagens by fluorine-substitution, 4-methylquinoline (4-MeQ), the most mutagenic form of all the quinoline derivatives examined so far, was used as a target in the present study. Five mono- and di-fluorinated derivatives of 4-MeQ, 2-fluoro-4-methylquinoline (2-F-3-MeQ), 6-F-4-MeQ, 7-F-4-MeQ, 2,6-difluoro-4-methylquinoline (2,6-diF-4-MeQ), and 2,7-diF-4-MeQ, were subjected to analysis of their structure-mutagenicity relationships. The 2-fluorinated derivatives (2-F-4-MeQ, 2,6-diF-4-MeQ, and 2,7-diF-4-MeQ) were all non-mutagenic In the Ames test. 7-F-4-MeQ was as highly mutagenic as, and 6-F-4-MeQ was less mutagenic than non-fluorinated 4-MeQ. Metabolic studies were also conducted with 4-MeQ, 2-F-4-MeQ, 6-F-4-MeQ, and 7-F-4-MeQ, using a liver microsomal enzyme fraction prepared from the 3-methylcholanthrene-treated rat. The HPLC analytical data showed that, although the metabolic patterns (hydroxylation at 4-methyl group as a main metabolic pathway and 3-hydroxylation as a minor pathway) of these four F-MeQs were similar to one another, only the 3-hydroxy metabolite of 2-F-4-MeQ was not produced under the present experimental conditions employed. These results suggest that fluorine-substitution at position 2 of 4-MeQ inhibited the formation of the enamine epoxide in the pyridine moiety and deprived this molecule of mutagenicity as in the case of quinoline. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(99)00226-0
• 作为产物：
  描述：

  N-Boc2-碘-4-氟苯胺 在 lithium chloro-isopropyl-magnesium chloride 、 caesium carbonate 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 2.17h， 生成 6-fluoro-4-methylquinoline
  参考文献：
  名称：

  通过分子内将芳基阴离子加到羰基碳上来高效合成取代的喹啉

  摘要：

  由取代的2-碘苯胺的Boc酰胺和烷基乙烯基酮分三步合成取代的喹啉。该方法包括：（1）在MeCN中在Cs 2 CO 3存在下，将2-碘苯胺的Boc酰胺N-迈克尔加成到烷基乙烯基酮上；（2）将加合物与3.5当量的i- PrMgCl·LiCl进行I-Mg交换，以及（3）所得醇的酸催化反应（EtOH中过量的AcCl）。给出了六个具有高收率的示例。

  DOI：

  10.1016/j.tetlet.2012.05.003

文献信息

• 6-O-SUBSTITUTED BENZOXAZOLE AND BENZOTHIAZOLE COMPOUNDS AND METHODS OF INHIBITING CSF-1R SIGNALING
  申请人：Sutton C James

  公开号：US20080045528A1

  公开（公告）日：2008-02-21

  Benzoxazole and benzothiazole compounds and the stereoisomers, tautomers, solvates, oxides, esters, and prodrugs thereof and pharmaceutically acceptable salts thereof are disclosed. Compositions of the compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier, and uses of the compounds, either alone or in combination with at least one additional therapeutic agent are also disclosed. The embodiments are useful for inhibiting cellular proliferation, inhibiting the growth and/or metathesis of tumors, treating or preventing cancer, treating or preventing degenerating bone diseases such as rheumatoid arthritis, and/or inhibiting molecules such as CSF-1R.

  苯并噁唑和苯并噻唑化合物及其立体异构体、互变异构体、溶剂合物、氧化物、酯类和前药以及其药学上可接受的盐已被披露。所述化合物的组合物，无论是单独使用还是与至少一种额外治疗剂组合，并与药学上可接受的载体一起使用的用途也已被披露。这些实施例可用于抑制细胞增殖，抑制肿瘤的生长和/或交换反应，治疗或预防癌症，治疗或预防类风湿性关节炎等退行性骨病，以及/或抑制CSF-1R等分子。
• Visible-light-mediated photoredox decarbonylative Minisci-type alkylation with aldehydes under ambient air conditions
  作者：Zhongzhen Wang、Xiaochen Ji、Jinwu Zhao、Huawen Huang

  DOI：10.1039/c9gc03008e

  日期：——

  Photocatalytic aerobic decarbonylative C–C coupling/alkylations of N-heteroarenes with aldehydes have been disclosed for the first time.

  首次披露了N-杂环烃与醛的光催化空气氧化脱羰基C-C偶联/烷基化反应。
• Metal‐Free Chemoselective Oxidation of 4‐Methylquinolines into Quinoline‐4‐Carbaldehydes
  作者：Jincheng Xu、Yang Li、Tianling Ding、Hao Guo

  DOI：10.1002/asia.202100704

  日期：2021.10.18

  A metal-free chemoselective oxidation of 4-methylquinolines into the corresponding aldehydes using phenyliodine(III) diacetate as the oxidant. This mild oxidation method provides an attractive alternative for synthesis of N-heteroaromatic aldehydes.

  使用二乙酸苯碘 (III) 作为氧化剂将 4-甲基喹啉无金属化学选择性氧化成相应的醛。这种温和的氧化方法为合成N-杂芳醛提供了一种有吸引力的替代方法。
• 一种醚类化合物与喹啉类衍生物交叉偶联的 方法
  申请人：湘潭大学

  公开号：CN109776406B

  公开（公告）日：2021-05-04

  本发明涉及一种醚类化合物与喹啉类衍生物交叉偶联的方法。本发明首次采用在Ir类化合物催化下，在氮气氛围中，将喹啉类化合物，醚类化合物转化为多取代喹啉及衍生物，制得分子结构稳定，化学性质优良。合成方法的反应原料廉价易得，且不需要经过预处理；反应只需要使用水、溴化锂、酸和铱催化剂，节约原材料，减少反应成本；整个反应体系简单，反应条件温和，反应设备较少，实验操作简便，用料来源广泛。
• LiBr‐Promoted Photoredox Minisci‐Type Alkylations of Quinolines with Ethers
  作者：Zhongzhen Wang、Xiaochen Ji、Tonghao Han、Guo‐Jun Deng、Huawen Huang

  DOI：10.1002/adsc.201901168

  日期：2019.12.17

  A visible‐light‐mediated photoredox Minisci‐type alkylation with ethers as the alkylating reagent is reported. User‐friendly LiBr has been found to be the key promoter for this radical coupling. The reaction exhibits broad functional group tolerance for both C2 and C4 couplings/alkylations of quinolines. Mechanistic studies suggest that the bromide additive could not only dramatically enhance the reaction

  据报道以醚为烷基化试剂的可见光介导的光氧化还原Minisci型烷基化。已发现用户友好的LiBr是这种自由基偶联的关键促进剂。该反应对喹啉的C 2和C 4偶合/烷基化均表现出宽泛的官能团耐受性。机理研究表明，溴化物添加剂不仅可以显着增强反应，而且还可能在还原催化循环中改变反应机理。