tert-butyl (2S)-4-tert-butyl-2-trimethylsilylpiperazine-1-carboxylate | 1236273-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl (2S)-4-tert-butyl-2-trimethylsilylpiperazine-1-carboxylate
• CAS: 1236273-34-9
• 化学式: C₁₆H₃₄N₂O₂Si
• 分子量: 314.544
• InChiKey: DNEYGJHFEFKOSQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 tert-butyl 4-tert-butylpiperazine-1-carboxylate 在 四甲基乙二胺 、 仲丁基锂 、 C₁₃H₂₇N₂O^(1-)*Li⁽¹⁺⁾ 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 5.0h， 生成 tert-butyl (2S)-4-tert-butyl-2-trimethylsilylpiperazine-1-carboxylate 、
  参考文献：
  名称：

  Dynamic thermodynamic resolution of lithiated N-Boc-N′-alkylpiperazines

  摘要：

  Deprotonation of N-Boc-N'-alkylpiperazines with sec-BuLi in Et(2)O-TMEDA gave the 2-lithio derivatives which were resolved in the presence of a chiral ligand. The best ligands for the asymmetric substitution were diamino-alkoxides that promoted a dynamic thermodynamic resolution (DTR) of the organolithium at -30 degrees C. Electrophilic quench gave enantiomerically enriched 2-substituted piperazines. Of a selection of piperazines, the N'-t-butyl derivative gave the best results, with the product N-Boc-N'-t-butyl-2-substituted piperazines being formed with enantiomer ratios up to 81:19. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.019

文献信息

• Dynamic thermodynamic resolution of lithiated N-Boc-N′-alkylpiperazines
  作者：Steven P. Robinson、Nadeem S. Sheikh、Carl A. Baxter、Iain Coldham

  DOI：10.1016/j.tetlet.2010.05.019

  日期：2010.7

  Deprotonation of N-Boc-N'-alkylpiperazines with sec-BuLi in Et(2)O-TMEDA gave the 2-lithio derivatives which were resolved in the presence of a chiral ligand. The best ligands for the asymmetric substitution were diamino-alkoxides that promoted a dynamic thermodynamic resolution (DTR) of the organolithium at -30 degrees C. Electrophilic quench gave enantiomerically enriched 2-substituted piperazines. Of a selection of piperazines, the N'-t-butyl derivative gave the best results, with the product N-Boc-N'-t-butyl-2-substituted piperazines being formed with enantiomer ratios up to 81:19. (C) 2010 Elsevier Ltd. All rights reserved.