4-(三氟甲基)喹啉-2-羧酸甲酯 | 1260890-34-3

• 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
• 中文名称: 4-(三氟甲基)喹啉-2-羧酸甲酯
• 英文名称: methyl 4-(trifluoromethyl)quinoline-2-carboxylate
• CAS: 1260890-34-3
• 化学式: C₁₂H₈F₃NO₂
• 分子量: 255.196
• InChiKey: LRQXJPIQMAKBPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(三氟甲基)喹啉-2-羧酸甲酯 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.75h， 以95%的产率得到4-三氟甲基喹啉-2-甲酸
  参考文献：
  名称：

  On the Mechanism of the Palladium-Catalyzed tert-Butylhydroperoxide-Mediated Wacker-Type Oxidation of Alkenes Using Quinoline-2-Oxazoline Ligands

  摘要：

  The mechanism of the tert-butylhydroperoxide-mediated, Pd(Quinox)-catalyzed Wacker-type oxidation was investigated to evaluate the hypothesis that a selective catalyst-controlled oxidation could be achieved by rendering the palladium coordinatively saturated using a bidentate amine ligand. The unique role of the Quinox ligand framework was probed via systematic ligand modifications. The modified ligands were evaluated through quantitative Hammett analysis, which supports a "push-pull" relationship between the electronically asymmetric quinoline and oxazoline ligand modules.

  DOI：

  10.1021/ja2017043
• 作为产物：
  描述：

  4-三氟甲基-2-羟基喹啉 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 三溴氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 4-(三氟甲基)喹啉-2-羧酸甲酯
  参考文献：
  名称：

  On the Mechanism of the Palladium-Catalyzed tert-Butylhydroperoxide-Mediated Wacker-Type Oxidation of Alkenes Using Quinoline-2-Oxazoline Ligands

  摘要：

  The mechanism of the tert-butylhydroperoxide-mediated, Pd(Quinox)-catalyzed Wacker-type oxidation was investigated to evaluate the hypothesis that a selective catalyst-controlled oxidation could be achieved by rendering the palladium coordinatively saturated using a bidentate amine ligand. The unique role of the Quinox ligand framework was probed via systematic ligand modifications. The modified ligands were evaluated through quantitative Hammett analysis, which supports a "push-pull" relationship between the electronically asymmetric quinoline and oxazoline ligand modules.

  DOI：

  10.1021/ja2017043