| 194494-97-8

• CAS: 194494-97-8
• 化学式: C₁₅H₁₄O₄W
• 分子量: 442.124
• InChiKey: HRCZBKKBPZKGIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 在 imidazole 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到
  参考文献：
  名称：

  Siloxy Effect on Intramolecular Cyclization of Tungsten−η¹-Siloxypropargyl Complexes:  Formation of 2,5-Dihydrofurans versus γ-Lactones

  摘要：

  Treatment of tungsten-eta(1)-4-(triethylsiloxy)propargyl and eta(1)-4-(tripropylsiloxy)propargyl compounds 8a-d and 9a-d with CF3CO2H in cold CH2Cl2 yielded a mixture of tungsten eta(1)-2,5-dihydrofurans 10a-d and eta(3)-syn-gamma-lactones 4a-d. The product ratios depend on the types of alkyl and siloxy substituents of the propargyl ligand; eta(1)-2,5-dihydrofurans 10a-d were formed in significant amount when the substituent is a secondary alkyl group. This cyclization pathway is in sharp contrast to our previous report that the dimethyl-tert-butylsiloxy group yielded only eta(3)-syn-gamma-lactones 4a-d. To validate this reaction on a complex system, we prepared the chiral tungsten-eta(1)-4-(triethylsiloxy)propargyl species 12b, which ultimately gave optically active tungsten eta(1)-2,5-dihydrofuran 13 in 68% yields. in connection with our previous report, we elaborated three types of cyclization reactions on chiral tungsten eta(1)-propargylic triols 12a-c, to afford chiral eta(1)-2,5-dihydrofurans and unsaturated gamma-and delta-lactones in reasonable yields.

  DOI：

  10.1021/om970335y