(4S,5R)-1-benzyl-4-(tert-butyldimethyl-silanyloxy)-5-[2-oxo-2-phenylethyl]-pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-1-benzyl-4-(tert-butyldimethyl-silanyloxy)-5-[2-oxo-2-phenylethyl]-pyrrolidin-2-one
• 英文别名: (4S,5R)-1-benzyl-4-[tert-butyl(dimethyl)silyl]oxy-5-phenacylpyrrolidin-2-one
• 化学式: C₂₅H₃₃NO₃Si
• 分子量: 423.627
• InChiKey: UHPMWEKBVQYSDP-GGAORHGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3S)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-5-oxopyrrolidin-2-yl diacetate 、 1-苯基-1-三甲基硅氧乙烯 在 三异丙基硅基三氟甲磺酸酯 作用下， 以 甲苯 为溶剂， 反应 4.5h， 以70%的产率得到(4S,5R)-1-benzyl-4-(tert-butyldimethyl-silanyloxy)-5-[2-oxo-2-phenylethyl]-pyrrolidin-2-one
  参考文献：
  名称：

  Toward Improving the Chemistry of N-Acyliminium Ions:  Nucleophilic Substitution Reactions of Pyrrolidinone Derivatives with Trialkylsilyl Nucleophiles Catalyzed by Triisopropylsilyltrifluoromethane Sulfonate (TIPSOTf)

  摘要：

  Nucleophilic substitution reactions of racemic and chiral 5-acetoxy-, 5-ethoxy-, and 5-methoxypyrrolidin-2-ones by silicon-based nucleophiles were efficiently catalyzed by TIPSOTf. This process was found to be general and accommodates a broad range of substrate-nucleophile combinations.

  DOI：

  10.1021/ol050576z

文献信息

• Eco-friendly N-acyliminium ion chemistry: solvent-free HNTf2 and TIPSOTf-catalyzed α-amidoalkylation of silicon-based π-nucleophiles
  作者：Marie-José Tranchant、Charlotte Moine、Raja Ben Othman、Till Bousquet、Mohamed Othman、Vincent Dalla

  DOI：10.1016/j.tetlet.2006.04.090

  日期：2006.6

  The alpha-amidoalkylation of silicon-based pi-nucleophiles is efficiently catalyzed by HNTf2 or TIPSOTf at very low levels of loading in neat conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• Toward Improving the Chemistry of <i>N</i>-Acyliminium Ions:  Nucleophilic Substitution Reactions of Pyrrolidinone Derivatives with Trialkylsilyl Nucleophiles Catalyzed by Triisopropylsilyltrifluoromethane Sulfonate (TIPSOTf)
  作者：Raja Ben Othman、Till Bousquet、Anthony Fousse、Mohamed Othman、Vincent Dalla

  DOI：10.1021/ol050576z

  日期：2005.7.1

  Nucleophilic substitution reactions of racemic and chiral 5-acetoxy-, 5-ethoxy-, and 5-methoxypyrrolidin-2-ones by silicon-based nucleophiles were efficiently catalyzed by TIPSOTf. This process was found to be general and accommodates a broad range of substrate-nucleophile combinations.