(3S,5S)-3-[3-(tert-butoxy-carbonyl)-aminopropyl]-5-phenylmethyl-2-oxopiperazine | 1408237-98-8

• 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)-3-[3-(tert-butoxy-carbonyl)-aminopropyl]-5-phenylmethyl-2-oxopiperazine
• CAS: 1408237-98-8
• 化学式: C₁₉H₂₉N₃O₃
• 分子量: 347.458
• InChiKey: WWIUHNDSJOQSDL-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  79.46
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (S)-methyl 5-[(tert-butoxycarbonyl)amino]-2-[((S)-1-cyano-2-phenylethyl)amino]-pentanoate 在 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以71%的产率得到(3S,5S)-3-[3-(tert-butoxy-carbonyl)-aminopropyl]-5-phenylmethyl-2-oxopiperazine
  参考文献：
  名称：

  A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles

  摘要：

  Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.009