6-((tert-butyldimethylsilyl)oxy)-1-methyl-2,3,4,5-tetrahydropyridin-1-ium trifluoromethanesulfonate | 1262117-63-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 6-((tert-butyldimethylsilyl)oxy)-1-methyl-2,3,4,5-tetrahydropyridin-1-ium trifluoromethanesulfonate
• CAS: 1262117-63-4
• 化学式: CF₃O₃S*C₁₂H₂₆NOSi
• 分子量: 377.5
• InChiKey: NZECLEBRNMNQEV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-((tert-butyldimethylsilyl)oxy)-1-methyl-2,3,4,5-tetrahydropyridin-1-ium trifluoromethanesulfonate 、 N-2,4,6-trimethylphenylsulfonylbenzaldimine 在 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以38%的产率得到1-methyl-3-[phenyl(2,4,6-mesitylenesulfonylamino)methyl]piperidin-2-one
  参考文献：
  名称：

  Catalytic Silicon-Mediated Carbon−Carbon Bond-Forming Reactions of Unactivated Amides

  摘要：

  In the presence of catalytic amounts of trialkylsilyl triflate and triethylamine, unactivated amides react with imines to afford the corresponding Mannich-type adducts in high yields with high anti selectivities. While silicon enolates have been widely used in organic synthesis for four decades, this is the first example of the catalytic use of the silicon species, to the best of our knowledge. Moreover, it is noteworthy that unactivated simple amides bearing a-protons that are less acidic than those of ketones and aldehydes can be successfully used in catalytic direct-type addition reactions. Finally, a preliminary trial of an asymmetric catalytic version was conducted and showed promising enantioselectivity of the desired product.

  DOI：

  10.1021/ja108764d