(t)Bu2Zn(TMP)Li | 225942-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (t)Bu2Zn(TMP)Li
• 英文别名: lithium;zinc;2-methylpropane;2,2,6,6-tetramethylpiperidin-1-ide
• CAS: 225942-46-1
• 化学式: C₁₇H₃₆LiNZn
• 分子量: 326.811
• InChiKey: LLIVOSJWJZDOBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (t)Bu2Zn(TMP)Li 、 苯甲醚 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Structure and Reaction Pathway of TMP-Zincate:  Amido Base or Alkyl Base?

  摘要：

  The novel directed ortho metalation (DoM) reagents for functionalized aromatic rings, TMP-Zn-ates (R2Zn(TMP)Li (R = Me, 1; tBu, 2)), have been reported to be synthetically useful for the chemo- and regioselective construction of multi-functionalized aromatic compounds. Here, we present the first comprehensive structural and mechanistic investigation by means of X-ray, NMR, and DFT studies on the DoM reaction employing our original TMP-Zn-ate base. The structures of TMP-Zn-ates in solution and in the solid state were determined. The DFT study strongly suggested that the deprotonation involving the TMP ligand on the TMP-Zn-ate is kinetically more favorable than that involving the alkyl ligand, and this view was supported by monitoring of the 13C NMR spectrum of the reaction mixture.

  DOI：

  10.1021/ja060489h