tert-butyl 2-[5-(trifluoromethyl)-2-pyridyl]acetate | 790714-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl 2-[5-(trifluoromethyl)-2-pyridyl]acetate
• 英文别名: tert-Butyl 2-(5-(trifluoromethyl)pyridin-2-yl)acetate；tert-butyl 2-[5-(trifluoromethyl)pyridin-2-yl]acetate
• CAS: 790714-75-9
• 化学式: C₁₂H₁₄F₃NO₂
• 分子量: 261.244
• InChiKey: QNSFRXRIDHXQLV-UHFFFAOYSA-N

物化性质

• 沸点：
  271.6±35.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[5-(trifluoromethyl)-2-pyridyl]acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(5-三氟甲基-吡啶-2-基)-乙酸
  参考文献：
  名称：

  Optimization of a series of quinazolinone-derived antagonists of CXCR3

  摘要：

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.032
• 作为产物：
  描述：

  (2-tert-butoxy-2-oxoethyl)zinc(II) bromide 、 2-溴-5-(三氟甲基)吡啶 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以69%的产率得到tert-butyl 2-[5-(trifluoromethyl)-2-pyridyl]acetate
  参考文献：
  名称：

  钯锌配合物的可见光吸收实现光诱导的钯催化的Negishi交叉偶联。

  摘要：

  通过激活Pd 0 -Zn络合物，可以实现可见光诱导的Negishi交叉耦合。通过这种光催化方法，可用于Negishi偶联的失活芳基卤化物的范围大大扩大。在有光和无光条件下进行的NMR实验证实，钯锌络合物的形成是加速氧化加成步骤的关键。

  DOI：

  10.1002/anie.201808654

文献信息

• Palladium-catalysed α-arylation of esters and amides under microwave conditions
  作者：Emilie Bentz、Mark G. Moloney、Susan M. Westaway

  DOI：10.1016/j.tetlet.2004.08.074

  日期：2004.9

  A rapid and convenient approach for the alpha-arylation of esters and amides using Reformatsky reagents under a microwave accelerated reaction protocol has been established. (C) 2004 Elsevier Ltd. All rights reserved.
• Photoinduced Palladium‐Catalyzed Negishi Cross‐Couplings Enabled by the Visible‐Light Absorption of Palladium–Zinc Complexes
  作者：Irini Abdiaj、Lena Huck、José Miguel Mateo、Antonio de la Hoz、M. Victoria Gomez、Angel Díaz‐Ortiz、Jesús Alcázar

  DOI：10.1002/anie.201808654

  日期：2018.10

  A visible‐light‐induced Negishi cross‐coupling is enabled by the activation of a Pd0–Zn complex. With this photocatalytic method, the scope of deactivated aryl halides that can be employed in the Negishi coupling was significantly expanded. NMR experiments conducted in the presence and absence of light confirmed that the formation of the palladium–zinc complex is key for accelerating the oxidative

  通过激活Pd 0 -Zn络合物，可以实现可见光诱导的Negishi交叉耦合。通过这种光催化方法，可用于Negishi偶联的失活芳基卤化物的范围大大扩大。在有光和无光条件下进行的NMR实验证实，钯锌络合物的形成是加速氧化加成步骤的关键。
• Optimization of a series of quinazolinone-derived antagonists of CXCR3
  作者：Jiwen Liu、Zice Fu、An-Rong Li、Michael Johnson、Liusheng Zhu、Andrew Marcus、Jay Danao、Tim Sullivan、George Tonn、Tassie Collins、Julio Medina

  DOI：10.1016/j.bmcl.2009.07.032

  日期：2009.9

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.