tris(3-mesitylpyrazol-1-yl)methane | 1000872-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tris(3-mesitylpyrazol-1-yl)methane
• 英文别名: tris(3-mesitylpyrazolyl)methane；Tpm(Ms)；1-[Bis[3-(2,4,6-trimethylphenyl)pyrazol-1-yl]methyl]-3-(2,4,6-trimethylphenyl)pyrazole
• CAS: 1000872-04-7
• 化学式: C₃₇H₄₀N₆
• 分子量: 568.765
• InChiKey: YLIYAGNWGFMNIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(l) iodide 、 tris(3-mesitylpyrazol-1-yl)methane 、 乙腈 以 乙腈 为溶剂， 以84%的产率得到[(tris(3-mesitylpyrazolyl)methane)Cu(acetonitrile)]2[Cu2I4]*(acetonitrile)
  参考文献：
  名称：

  Copper(I) Complexes with Trispyrazolylmethane Ligands: Synthesis, Characterization, and Catalytic Activity in Cross-Coupling Reactions

  摘要：

  Three novel Cu(I) complexes bearing tris(pyrazolyl)-methane ligands, Tpm(x), have been prepared from reactions of equimolar amounts of CuI and the ligands Tpm, (HC(pz)(3)), Tpm*, (HC(3,5-Me-2-pz)(3)), and Tpm(Ms), (HC(3-Ms-pz)(3)). X-ray diffraction studies have shown that the Tpm and Tpm(Ms) derivatives exhibit a 2:1 Cu:ligand ratio, whereas the Tpm* complex is a mononuclear species in nature. The latter has been employed as a precatalyst in the aryladon of amides and aromatic thiols with good activity. The synthesis of a Tpm*Cu(I)-phthalimidate, a feasible intermediate in this catalytic process, has also been performed. Low temperature H-1 NMR studies in CDCl3 have indicated that this complex exists in solution as a mixture of two, neutral and ionic forms. Conductivity measurements have reinforced this proposal, the ionic form predominating in a very polar solvent such as DMSO. The reaction of Tpm*Cu(I)-phthalimidate with iodobenzene afforded the expected C-N coupling product in 76% yield accounting for its role as an intermediate in this transformation.

  DOI：

  10.1021/ic300843a

文献信息

• Catalytic Carbon−Hydrogen Bond Functionalization in an Ionic Liquid Medium
  作者：Pilar Rodríguez、Eleuterio Álvarez、M. Carmen Nicasio、Pedro J. Pérez

  DOI：10.1021/om700822a

  日期：2007.12.1

  The functionalization of unreactive C-H bonds of several hydrocarbons has been achieved at room temperature by the formal insertion of carbene/CHCO2Et units (from ethyl diazoacetate) into such bonds, using copper-based catalysts in a biphasic reaction medium (ionic liquid-hydrocarbon). Catalyst and product separation has been carried out easily, and the recycle of the catalyst for five cycles has been achieved without any loss of catalytic activity.