5-(三氟甲基)吡啶-2-硼酸频那醇酯 | 1101205-23-5

• 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
• 中文名称: 5-(三氟甲基)吡啶-2-硼酸频那醇酯
• 英文名称: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine
• CAS: 1101205-23-5
• 化学式: C₁₂H₁₅BF₃NO₂
• 分子量: 273.063
• InChiKey: LNTCLMJOCYHWEW-UHFFFAOYSA-N

物化性质

• 沸点：
  307.3±42.0 °C(Predicted)
• 密度：
  1.18

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-(三氟甲基)吡啶-2-硼酸频那醇酯 在 caesium carbonate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 5,5'-二(三氟甲基)-2,2'-联吡啶
  参考文献：
  名称：

  Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates

  摘要：

  The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(l) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope Is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.

  DOI：

  10.1021/ol802556f

文献信息

• Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates
  作者：James Z. Deng、Daniel V. Paone、Anthony T. Ginnetti、Hideki Kurihara、Spencer D. Dreher、Steven A. Weissman、Shaun R. Stauffer、Christopher S. Burgey

  DOI：10.1021/ol802556f

  日期：2009.1.15

  The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(l) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope Is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.