diisopropyl pyrazin-2-yl-phosphonate | 1073561-74-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diisopropyl pyrazin-2-yl-phosphonate
• 英文别名: 2-Di(propan-2-yloxy)phosphorylpyrazine
• CAS: 1073561-74-6
• 化学式: C₁₀H₁₇N₂O₃P
• 分子量: 244.23
• InChiKey: VTGLINDYRURVKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯吡嗪 、 亚磷酸二异丙酯 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以97%的产率得到diisopropyl pyrazin-2-yl-phosphonate
  参考文献：
  名称：

  Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates

  摘要：

  The palladium-catalyzed cross-coupling of dialkylphosphite with aromatic electrophiles (Hirao coupling) was re-investigated. Some limitations in terms of palladium loadings and substrate reactivity are alleviated with the use of Pd(OAc)(2) complexed to 1,1'-bis(diphenylphosphino) ferrocene (dppf) as a ligand. Various aryl and heteroaryl halides are employed to deliver both known and novel substituted phosphonates. The first examples of aryl chloride couplings are also reported. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.07.020

文献信息

• Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates
  作者：Yamina Belabassi、Saeed Alzghari、Jean-Luc Montchamp

  DOI：10.1016/j.jorganchem.2008.07.020

  日期：2008.9

  The palladium-catalyzed cross-coupling of dialkylphosphite with aromatic electrophiles (Hirao coupling) was re-investigated. Some limitations in terms of palladium loadings and substrate reactivity are alleviated with the use of Pd(OAc)(2) complexed to 1,1'-bis(diphenylphosphino) ferrocene (dppf) as a ligand. Various aryl and heteroaryl halides are employed to deliver both known and novel substituted phosphonates. The first examples of aryl chloride couplings are also reported. (C) 2008 Elsevier B.V. All rights reserved.