(2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-methyl-2'-oxopiperazin-1'-yl]acetic acid | 186821-12-5

• 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: (2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-methyl-2'-oxopiperazin-1'-yl]acetic acid
• 英文别名: (2S)-4-methyl-2-[(3S)-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxopiperazin-1-yl]pentanoic acid
• CAS: 186821-12-5
• 化学式: C₁₆H₂₈N₂O₅
• 分子量: 328.409
• InChiKey: UYIYWZANZBHGFT-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-methyl-2'-oxopiperazin-1'-yl]acetic acid 在 N-甲基吗啉 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S)-4-methyl-2-[(3S)-3-methyl-2-oxo-4-[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]piperazin-1-yl]pentanoate
  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：

  N-allyl (L)-leucine methyl ester 在 N-甲基吗啉 、 lithium hydroxide monohydrate 、 水 、 1-羟基苯并三唑 、 臭氧 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.42h， 生成 (2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-methyl-2'-oxopiperazin-1'-yl]acetic acid
  参考文献：
  名称：

  OLIGOOXOPIPERAZINES AND METHODS OF MAKING AND USING THEM

  摘要：

  本发明涉及寡氧代哌嗪及其用途。还公开了制备寡氧代哌嗪的方法。

  公开号：

  US20120040992A1

文献信息

• Oligooxopiperazines as Nonpeptidic α-Helix Mimetics
  作者：Petra Tošovská、Paramjit S. Arora

  DOI：10.1021/ol1003143

  日期：2010.4.2

  A new class of nonpeptidic alpha-helix mimetics derived from alpha-amino acids and featuring chiral backbones Is described. NMR and circular dichroism spectroscopies, In combination with molecular modeling studies, provide compelling evidence that oligooxopiperazine dimers adopt stable conformations that reproduce the arrangement of i, i+4, and i+7 residues on an alpha-helix.
• OLIGOOXOPIPERAZINES AND METHODS OF MAKING AND USING THEM
  申请人：Arora Paramjit S.

  公开号：US20120040992A1

  公开（公告）日：2012-02-16

  The present invention relates to oligooxopiperazines and their use. Methods for preparing oligooxopiperazines are also disclosed.

  本发明涉及寡氧代哌嗪及其用途。还公开了制备寡氧代哌嗪的方法。
• 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.