methyl 1,4-dihydro-4-oxo-6-trifluoromethylquinoline-2-carboxylate | 1422284-64-7

• 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: methyl 1,4-dihydro-4-oxo-6-trifluoromethylquinoline-2-carboxylate
• 英文别名: 6-trifluoromethyl-quinolin-4(1H)-one-2-carboxylic acid methyl ester；methyl 6-trifluoromethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate；methyl 4-oxo-6-(trifluoromethyl)-1H-quinoline-2-carboxylate
• CAS: 1422284-64-7
• 化学式: C₁₂H₈F₃NO₃
• 分子量: 271.196
• InChiKey: MXGPEAHFOPWZAV-UHFFFAOYSA-N

物化性质

• 沸点：
  411.6±40.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 1,4-dihydro-4-oxo-6-trifluoromethylquinoline-2-carboxylate 在 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1,4-dihydro-N′-(2,5-dimethylpyrrol-1-yl)-4-oxo-6-trifluoromethylquinoline-2-carbohydrazide
  参考文献：
  名称：

  喹诺酮类似物12：2-取代的4-喹诺酮及其相关化合物的合成和互变异构体

  摘要：

  4-喹诺酮-2-羧酸4A，B被转换成4-喹诺酮-2-碳酰肼5a，5b中，腙6,7,10，和相关的化合物8,9,11。4-甲氧基喹啉-2-羧酸酯12也被转化为4-甲氧基喹啉-2-碳酰肼13，其被改性为hydr 14和相关化合物15。描述了化合物6b和14的抗菌活性，以及化合物4-11在氘代二甲基亚砜和氘代三氟乙酸中的4-氧代和4-羟基互变异构体。

  DOI：

  10.1002/jhet.922
• 作为产物：
  描述：

  对三氟甲基苯胺 、 丁炔二酸二甲酯 在 copper(l) iodide 、 三氟甲磺酸 、 三氟甲磺酸酐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以46%的产率得到methyl 1,4-dihydro-4-oxo-6-trifluoromethylquinoline-2-carboxylate
  参考文献：
  名称：

  铜（I）催化苯胺与炔烃的环化反应，合成喹诺酮类和二氢庚二酮类化合物

  摘要：

  已经开发了一种独特而有效的方法，可通过Cu（I）催化的直接环化反应，从简单易用的伯胺和炔烃一锅合成多种4-喹诺酮。还发现（硫代）苯酚是该反应的可见底物。此外，通过使用仲苯胺作为通用底物，已经证明了前所未有的二氢硬脂酸二酮的合成。

  DOI：

  10.1021/acs.orglett.8b00436

文献信息

• Kynurenic acid derivatives useful in the treatment of neurodegenerative
  申请人：Merck Sharp & Dohme Limited

  公开号：US05270309A1

  公开（公告）日：1993-12-14

  4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, other than carboxy or C.sub.1-6 alkoxycarbonyl, are novel compounds, as also are compounds of formula II ##STR1## wherein R.sup.2 represents carboxy or a group convertible thereto in vivo, R.sup.6 is hydrogen and R.sup.5 and R.sup.7 represent C.sub.1-6 alkyl or halogen, provided that R.sup.5 and R.sup.7 are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.

  具有2-酸性基团或可在体内转化为该基团的4-氧代-1,4-二氢喹啉化合物及其药用可接受的盐是N-甲基-D-天冬氨酸（NMDA）受体的有效特异性拮抗剂，因此在治疗神经退行性疾病方面具有用途。具有2-酸性基团或可在体内转化为该基团的4-氧代-1,4-二氢喹啉化合物，除了羧基或C.sub.1-6烷氧羰基之外，是新颖的化合物，公式II的化合物也是新颖的，其中R.sup.2代表羧基或可在体内转化为该基团的基团，R.sup.6为氢，R.sup.5和R.sup.7代表C.sub.1-6烷基或卤素，但要求R.sup.5和R.sup.7不能同时是氯或溴；描述了制备这些新颖化合物的方法，以及含有这些新颖化合物的药物组合物。
• Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0303387A1

  公开（公告）日：1989-02-15

  4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-­aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-­acidic group or a group convertible thereto in vivo, other than carboxy or C₁₋₆ alkoxycarbonyl, are novel compounds, as also are compounds of formula II wherein R² represents carboxy or a group convertible thereto in vivo, R⁶ is hydrogen and R⁵ and R⁷ represent C₁₋₆ alkyl or halogen, provided that R⁵ and R⁷ are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.

  具有 2-酸性基团或体内可转化基团的 4-氧代-1,4-二氢喹啉化合物及其药学上可接受的盐类是 N-甲基-D-天冬氨酸（NMDA）受体的强效特异性拮抗剂，因此可用于治疗神经退行性疾病。除羧基或 C₁₋₆ 烷氧羰基外，具有 2-酸性基团或在体内可转化的基团的 4-氧代-1,4-二氢喹啉化合物是新型化合物，如式 II 所示的化合物 其中 R² 代表羧基或体内可转化为羧基的基团，R⁶ 是氢，R⁵ 和 R⁷ 代表 C₁₋₆ 烷基或卤素，但 R⁵ 和 R⁷ 不能同时为氯或同时为溴。
• A novel series of N-(azetidin-3-yl)-2-(heteroarylamino)acetamide CCR2 antagonists
  作者：Nalin L. Subasinghe、James Lanter、Thomas Markotan、Evan Opas、Sandra McKenney、Carl Crysler、Cuifen Hou、John O’Neill、Dana Johnson、Zhihua Sui

  DOI：10.1016/j.bmcl.2012.12.017

  日期：2013.2

  The inflammatory response associated with the activation of C C chemokine receptor CCR2 via it's interaction with the monocyte chemoattractant protein-1 (MCP-1, CCL2) has been implicated in many disease states, including rheumatoid arthritis, multiple sclerosis, atherosclerosis, asthma and neuropathic pain. Small molecule antagonists of CCR2 have been efficacious in animal models of inflammatory disease, and have been advanced into clinical development. The necessity to attenuate hERG binding appears to be a common theme for many of the CCR2 antagonist scaffolds appearing in the literature, presumably due the basic hydrophobic motif present in all of these molecules. Following the discovery of a novel cyclohexyl azetidinylamide CCR2 antagonist scaffold, replacement of the amide bond with heterocyclic rings was explored as a strategy for reducing hERG binding and improving pharmacokinetic properties. (C) 2012 Elsevier Ltd. All rights reserved.
• OCTAHYDRO-CYCLOBUTA [1,2-C;3,4-C']DIPYRROLE DERIVATIVES AS AUTOTAXIN INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3074400B1

  公开（公告）日：2017-11-15
• US5270309A
  申请人：——

  公开号：US5270309A

  公开（公告）日：1993-12-14