1-Methyl-7-(trifluoromethyl)quinolin-4(1H)-one | 108494-53-7

• 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: 1-Methyl-7-(trifluoromethyl)quinolin-4(1H)-one
• 英文别名: 1-methyl-7-(trifluoromethyl)quinolin-4-one
• CAS: 108494-53-7
• 化学式: C₁₁H₈F₃NO
• 分子量: 227.186
• InChiKey: RUGYUXALEULWJE-UHFFFAOYSA-N

物化性质

• 沸点：
  283.0±40.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Methyl-7-(trifluoromethyl)quinolin-4(1H)-one 在 copper(l) iodide 、 三甲基氯硅烷 、 氧气 、 copper diacetate 、 sodium acetate 、 palladium diacetate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 5-methyl-3-(trifluoromethyl)-5H-indeno[2,1-b]quinoline-6,11-dione
  参考文献：
  名称：

  Discovery of wrightiadione as a novel template for the TrkA kinase inhibitors

  摘要：

  Enzymatic kinase assays and docking simulation studies have shown that the natural product wrightiadione displays inhibitory activity toward TrkA and PLK3. In this study, the template of wrightiadione served as a starting point for Trk inhibitor development campaigns. Molecular simulation provided structural insights for the design of derivatives that were efficiently generated by our recently developed 3-step tandem synthetic approach, resulting in the discovery of compound 2h with biochemical potency at the single-digit micromolar level. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.070

文献信息

• Rh(III) and Ru(II)-Catalyzed Site-Selective C–H Alkynylation of Quinolones
  作者：Dahye Kang、Sungwoo Hong

  DOI：10.1021/acs.orglett.5b00641

  日期：2015.4.17

  C2- and C5-alkynylated quinolone scaffolds are core structures of numerous biologically active molecules. Utilizing TIPS-EBX as an alkynylating agent, we have developed an efficient and site-selective C5 alkynylation of 4-quinolones that is directed by the weakly coordinating carbonyl group. In addition, Ru(II) catalyzed C2-selective alkynylation was successfully realized via N-pyrimidyl group-directed

  C2-和C5-炔基化喹诺酮骨架是众多生物活性分子的核心结构。利用TIPS-EBX作为烷基化剂，我们开发了由弱配位羰基控制的4-喹诺酮类的高效，位点选择性C5烷基化反应。此外，Ru（II）催化的C2选择性炔基化是通过N-嘧啶基定向的交叉偶联成功实现的，以访问有价值的C2炔基化的4-喹诺酮类。此策略可直接访问C2或C5炔基化4-喹诺酮类药物。此外，该反应被用于异喹诺酮以进行C 3-选择性炔基化。
• Tandem Dehydrogenation/Oxidation/Oxidative Cyclization Approach to Wrightiadione and Its Derivatives
  作者：Yujeong Jeong、Youngtaek Moon、Sungwoo Hong

  DOI：10.1021/acs.orglett.5b01618

  日期：2015.7.2

  Wrightiadione contains a unique tetracyclic isoflavone moiety and has been shown to exhibit a broad range of biological activities. An efficient and Straightforward synthetic method for generating the molecular complexity,of wrightiadione was developed, through three-step tandem dehydrogenation/oxidation/oxidative cyclization reactions with a Pd/Cu. catalytic system. This Unprecedented one-pot route utilizes a broad: range of substrates, providing a convenient and powerful synthetic tool for accessing naturally occurring tetracyclic isoflavone wrightiadione and its nitrogen-containing derivatives.
• Discovery of wrightiadione as a novel template for the TrkA kinase inhibitors
  作者：Yujeong Jeong、Sang Min Lim、Sungwoo Hong

  DOI：10.1016/j.bmcl.2015.09.070

  日期：2015.11

  Enzymatic kinase assays and docking simulation studies have shown that the natural product wrightiadione displays inhibitory activity toward TrkA and PLK3. In this study, the template of wrightiadione served as a starting point for Trk inhibitor development campaigns. Molecular simulation provided structural insights for the design of derivatives that were efficiently generated by our recently developed 3-step tandem synthetic approach, resulting in the discovery of compound 2h with biochemical potency at the single-digit micromolar level. (C) 2015 Elsevier Ltd. All rights reserved.