(1'S,3S)-4-(tert-butoxycarbonyl)-1-(1'-isobutyl-2'-hydroxyethyl)-3-methyl-2-oxopiperazine | 186820-95-1

• 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: (1'S,3S)-4-(tert-butoxycarbonyl)-1-(1'-isobutyl-2'-hydroxyethyl)-3-methyl-2-oxopiperazine
• 英文别名: tert-butyl (2S)-4-[(2S)-1-hydroxy-4-methylpentan-2-yl]-2-methyl-3-oxopiperazine-1-carboxylate
• CAS: 186820-95-1
• 化学式: C₁₆H₃₀N₂O₄
• 分子量: 314.425
• InChiKey: ICWJGJZSOGEUCN-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'S,3S)-4-(tert-butoxycarbonyl)-1-(1'-isobutyl-2'-hydroxyethyl)-3-methyl-2-oxopiperazine 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以87%的产率得到(2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-methyl-2'-oxopiperazin-1'-yl]acetic acid
  参考文献：
  名称：

  Efficient Synthesis of Conformationally Constrained Peptidomimetics Containing 2-Oxopiperazines¹

  摘要：

  The enantioselective synthesis of a series of peptides containing the 3-substituted 2-oxopiperazine system is reported. The method involves a direct diastereoselective alkylation of the N-(hydroxyalkyl)-2-oxopiperazine 3, prepared in three steps from methyl L-leucinate in 38% yield, followed by oxidation of the hydroxyl function. Esterification of the resulting acids 11 and then deprotection and acylation of N-4 afforded tripeptide analogues 16 substituted by a large variety of alkyl side chains at the 2-position of the 2-oxopiperazine.

  DOI：

  10.1021/jo961398d
• 作为产物：
  描述：

  (1'S)-4-(tert-butoxycarbonyl)-1-(1'-isobutyl-2'-hydroxyethyl)-2-oxopiperazine 、 碘甲烷 在 叔丁基锂 作用下， 生成 (1'S,3S)-4-(tert-butoxycarbonyl)-1-(1'-isobutyl-2'-hydroxyethyl)-3-methyl-2-oxopiperazine 、 4-((S)-1-Hydroxymethyl-3-methyl-butyl)-2,2-dimethyl-3-oxo-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Efficient Synthesis of Conformationally Constrained Peptidomimetics Containing 2-Oxopiperazines¹

  摘要：

  The enantioselective synthesis of a series of peptides containing the 3-substituted 2-oxopiperazine system is reported. The method involves a direct diastereoselective alkylation of the N-(hydroxyalkyl)-2-oxopiperazine 3, prepared in three steps from methyl L-leucinate in 38% yield, followed by oxidation of the hydroxyl function. Esterification of the resulting acids 11 and then deprotection and acylation of N-4 afforded tripeptide analogues 16 substituted by a large variety of alkyl side chains at the 2-position of the 2-oxopiperazine.

  DOI：

  10.1021/jo961398d

文献信息

• Efficient Synthesis of Conformationally Constrained Peptidomimetics Containing 2-Oxopiperazines¹
  作者：Adriana Pohlmann、Vincent Schanen、Dominique Guillaume、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1021/jo961398d

  日期：1997.2.1

  The enantioselective synthesis of a series of peptides containing the 3-substituted 2-oxopiperazine system is reported. The method involves a direct diastereoselective alkylation of the N-(hydroxyalkyl)-2-oxopiperazine 3, prepared in three steps from methyl L-leucinate in 38% yield, followed by oxidation of the hydroxyl function. Esterification of the resulting acids 11 and then deprotection and acylation of N-4 afforded tripeptide analogues 16 substituted by a large variety of alkyl side chains at the 2-position of the 2-oxopiperazine.