(2S)-2-(N-methoxy-N-methylcarbamoyl)-1-([2-trimethylsilyl]ethoxycarbonyl)pyrrolidine | 936649-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-(N-methoxy-N-methylcarbamoyl)-1-([2-trimethylsilyl]ethoxycarbonyl)pyrrolidine
• CAS: 936649-28-4
• 化学式: C₁₃H₂₆N₂O₄Si
• 分子量: 302.446
• InChiKey: VAOSPFZXWWLTDA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-(N-methoxy-N-methylcarbamoyl)-1-([2-trimethylsilyl]ethoxycarbonyl)pyrrolidine 、 magnesium,propan-2-ylbenzene,bromide 、 magnesium,ethenylbenzene,bromide 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 (2S)-2[(4-ethenylphenyl)(hydroxy)(4-{1-methylethyl}phenyl)methyl]-1-[(2-trimethylsilyl)ethoxycarbonyl]pyrrolidine 、 (2R)-2[(4-ethenylphenyl)(hydroxy)(4-{1-methylethyl}phenyl)methyl]-1-[(2-trimethylsilyl)ethoxycarbonyl]pyrrolidine
  参考文献：
  名称：

  Comparison of enantioselective reductions using bead and monolith ‘disk’ polymer formulations of CBS catalysts

  摘要：

  Two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst were prepared and examined. Polymeric beads, with the auxiliary bound in pendant and crosslinked fashion, were prepared utilizing an improved procedure based upon earlier work. Optimization of a procedure for ketone reduction gives results that match those in solution. Attempted reuse gave mixed results. For comparison purposes, CBS functionalized monoliths were formed and tested but performed poorly. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.048
• 作为产物：
  描述：

  N-(叔丁氧基羰基)-L-脯氨酸-N′-甲氧基-N′-甲酰胺 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 (2S)-2-(N-methoxy-N-methylcarbamoyl)-1-([2-trimethylsilyl]ethoxycarbonyl)pyrrolidine
  参考文献：
  名称：

  Comparison of enantioselective reductions using bead and monolith ‘disk’ polymer formulations of CBS catalysts

  摘要：

  Two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst were prepared and examined. Polymeric beads, with the auxiliary bound in pendant and crosslinked fashion, were prepared utilizing an improved procedure based upon earlier work. Optimization of a procedure for ketone reduction gives results that match those in solution. Attempted reuse gave mixed results. For comparison purposes, CBS functionalized monoliths were formed and tested but performed poorly. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.048