(2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-isobutyl-2'-oxopiperazin-1'-yl]acetic acid | 174585-12-7

• 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'-isobutyl-2'-oxopiperazin-1'-yl]acetic acid
• 英文别名: (2S)-4-methyl-2-[(3S)-4-[(2-methylpropan-2-yl)oxycarbonyl]-3-(2-methylpropyl)-2-oxopiperazin-1-yl]pentanoic acid
• CAS: 174585-12-7
• 化学式: C₁₉H₃₄N₂O₅
• 分子量: 370.489
• InChiKey: KZMUABJNBCOXCC-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 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'-isobutyl-2'-oxopiperazin-1'-yl]acetic acid 在 硼烷四氢呋喃络合物 作用下， 反应 48.0h， 生成 (2S,8S,11S,17S)-2,8,11,17-tetraisobutyl-1,4,7,10,13,16-hexaazatricyclo[14.2.2.2^7.10]docosane
  参考文献：
  名称：

  结构增强的大环多胺新型光学活性双核铜 (II) 配合物的合成和结构

  摘要：

  结构增强的手性 18 元氮杂大环 (2S,8S,11S,17S)-2,8,11,17-四异丁基-1,4,7,10 的光学活性 μ-氯和 μ-羟基双核铜 (II) 配合物,13,16-六氮杂三环[14. 2. 2. 27,10]二十二烷和20-元(2S,9S,12S,19S)-2,9,12,19-四异丁基-1,4,8,11,14,18-六氮杂三环[16. 2. 2. 28,11] 新合成并表征了通过从结构受限的大环假肽中还原 BH3 获得的二十四烷。

  DOI：

  10.1246/cl.1996.153
• 作为产物：
  描述：

  Boc-Gly-ψ(CH2NH)-Leu-OMe 在 sodium tetrahydroborate 、 jones reagent 、 叔丁基锂 、 sodium hydride 、 lithium chloride 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 29.92h， 生成 (2S,3'S)-2-isobutyl-2-[4'-(tert-butoxycarbonyl)-3'-isobutyl-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

文献信息

• 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。
• 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.
• Synthesis and Structure of Chiral Dinuclear Copper(II) Complex of Novel Structurally Reinforced Hexaazamacrocyclic Ligand
  作者：Yoshio Seki、Hiroyuki Miyake、Yoshitane Kojima、Mayumi Doi、Shigenobu Yano

  DOI：10.1080/10587259608039363

  日期：1996.2

  A structurally reinforced chiral 18-membered azamacrocycle (2S,8S, 11S, 17S)-2,8,11,17-tetraisobutyl-1,4,7,10,13,16-hexaazatricyclo [14.2.2.2(7,10)]docosane as a new type of ligand was conveniently synthesized by BH3 reduction from the corresponding constrained macrocyclic pseudopeptide cyclo[(2S,3'S)-2-(3'- isobutyl-2'-oxo-piperazine-1'-yl)-4-methyl-pentanoyl-glycyl](2). complexes were prepared and characterized.
• 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.
• Syntheses and Structures of Novel Optically Active Dinuclear Copper(II) Complexes of Structurally Reinforced Macrocyclic Polyamines
  作者：Yoshio Seki、Hiroyuki Miyake、Yoshitane Kojima

  DOI：10.1246/cl.1996.153

  日期：1996.2

  and μ-hydroxo dinuclear copper(II) complexes of structurally reinforced chiral 18-membered azamacrocycle (2S,8S,11S,17S)-2,8,11,17-tetraisobutyl-1,4,7,10,13,16-hexaazatricyclo[14. 2. 2. 27,10]docosane and 20-membered one (2S,9S,12S,19S)-2,9,12,19-tetraisobutyl-1,4,8,l1,14,18-hexaazatricyclo [16. 2. 2. 28,11] tetracosane obtained by BH3 reduction from structurally constrained macrocyclic pseudopeptides

  结构增强的手性 18 元氮杂大环 (2S,8S,11S,17S)-2,8,11,17-四异丁基-1,4,7,10 的光学活性 μ-氯和 μ-羟基双核铜 (II) 配合物,13,16-六氮杂三环[14. 2. 2. 27,10]二十二烷和20-元(2S,9S,12S,19S)-2,9,12,19-四异丁基-1,4,8,11,14,18-六氮杂三环[16. 2. 2. 28,11] 新合成并表征了通过从结构受限的大环假肽中还原 BH3 获得的二十四烷。