(3S,5S)-1,3-dibenzyl-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine | 1004286-97-8

• 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: (3S,5S)-1,3-dibenzyl-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine
• 英文别名: tert-butyl (2S,6S)-2,4-dibenzyl-6-methyl-3-oxopiperazine-1-carboxylate
• CAS: 1004286-97-8
• 化学式: C₂₄H₃₀N₂O₃
• 分子量: 394.514
• InChiKey: VVUYFANLQKEHQZ-RXVVDRJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5S)-1,3-dibenzyl-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到(S)-tert-butyl 4,6-dibenzyl-2-methyl-3,4-dihydropyrazine-1(2H)-carboxylate
  参考文献：
  名称：

  Synthesis of new polysubstituted piperazines and dihydro-2H-pyrazines by selective reduction of 2-oxo-piperazines

  摘要：

  New enantiomerically enriched 1,4,5-piperazines and 1,4,5-dihydro-2H-pyrazines have been prepared by reduction of the corresponding 2-oxo-piperazines. Selective reduction can be achieved by careful control of the reaction conditions using LiAlH4. Notably the two nitrogen atoms of the final compounds are orthogonally protected. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.025
• 作为产物：
  描述：

  (S)-1-benzyl-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine 、 溴甲苯 在 六甲基磷酰三胺 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 3.25h， 以43%的产率得到(3S,5S)-1,3-dibenzyl-4-tert-butoxycarbonyl-5-methyl-2-oxopiperazine
  参考文献：
  名称：

  A new versatile and diastereoselective synthesis of polysubstituted 2-oxopiperazines from naturally occurring amino acids

  摘要：

  A highly stereoselective approach to 1,3,4,5- and 1,3,3',4,5-polysubstituted 2-oxopiperazines is reported. The method is based on the synthetic elaboration of naturally occurring amino acids to obtain enantiomerically enriched C-5 substituted oxopiperazines, which are further functionalized at C-3 via enolate formation and reaction with electrophiles. Notably, the two nitrogens of the ring can be orthogonally protected. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.027