(3R,6R)-3,6-diisopropylpiperazine-2,5-dione | 57030-21-4

• 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: (3R,6R)-3,6-diisopropylpiperazine-2,5-dione
• 英文别名: cyclo-(D-Val)2；cyclo[D-Val-D-Val]；Cyclo-L-Val-L-Val；(3R,6R)-3,6-di(propan-2-yl)piperazine-2,5-dione
• CAS: 57030-21-4
• 化学式: C₁₀H₁₈N₂O₂
• 分子量: 198.265
• InChiKey: QGMAWEIDGADSAC-HTQZYQBOSA-N

物化性质

• 熔点：
  269-271 °C
• 沸点：
  428.7±38.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,6R)-3,6-diisopropylpiperazine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 (2R,5R)-2,5-Diisopropylpiperazine
  参考文献：
  名称：

  通过氢键和配位相互作用稳定的手性十八元三维超分子实体

  摘要：

  从十二个卟啉锌加成的2-（乙基氨基）-嘧啶[4,5- b ] [1,8]萘啶-4（3 ）在甲苯和氯仿中组装了一类新的手性十八组分三维超分子实体H）一单体和六种手性联吡啶化合物。杂环链段形成两个C 6对称的环状六聚体，它们由成熟的DDA-AAD氢键基序稳定，而六个手性双吡啶配体与相应的卟啉锌单元配位，形成两层结构。该结构的特点是11 H NMR，UV-vis和圆二色性实验也表明，当单体的浓度足够高时，手性超分子实体可以排他地形成。

  DOI：

  10.1016/j.tet.2010.04.009
• 作为产物：
  描述：

  D-缬氨酸 在 silica gel 作用下， 反应 0.1h， 生成 (3R,6R)-3,6-diisopropylpiperazine-2,5-dione
  参考文献：
  名称：

  通过氢键和配位相互作用稳定的手性十八元三维超分子实体

  摘要：

  从十二个卟啉锌加成的2-（乙基氨基）-嘧啶[4,5- b ] [1,8]萘啶-4（3 ）在甲苯和氯仿中组装了一类新的手性十八组分三维超分子实体H）一单体和六种手性联吡啶化合物。杂环链段形成两个C 6对称的环状六聚体，它们由成熟的DDA-AAD氢键基序稳定，而六个手性双吡啶配体与相应的卟啉锌单元配位，形成两层结构。该结构的特点是11 H NMR，UV-vis和圆二色性实验也表明，当单体的浓度足够高时，手性超分子实体可以排他地形成。

  DOI：

  10.1016/j.tet.2010.04.009

文献信息

• A Novel Approach to the Synthesis of Symmetric Optically Active 2,5-Dioxopiperazines
  作者：Vladimir A. Basiuk、Taras Yu. Gromovoy、Alexei A. Chuiko、Vadim A. Soloshonok、Valery P. Kukhar

  DOI：10.1055/s-1992-26131

  日期：——

  "Gas-solid-phase" method for the preparation of some cyclic dipeptides, 2,5-dioxopiperazines (diketopiperazines), is described. The method implies cyclodimerization of vaporous aliphatic α-amino acids in the presence of silica at reduced pressure and yields optically active 2,5-dioxopiperazines.

  描述了一种用于制备某些环状二肽和2,5-二氧庚哌嗪（双酮哌嗪）的“气固相”方法。该方法是在减少压力的情况下，在二氧化硅存在下，对气相脂肪族α-氨基酸进行环状二聚化，产生光学活性的2,5-二氧庚哌嗪。
• Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides
  作者：Christopher Bérubé、Xavier Barbeau、Sébastien Cardinal、Pierre-Luc Boudreault、Corinne Bouchard、Nicolas Delcey、Patrick Lagüe、Normand Voyer

  DOI：10.1080/10610278.2016.1236197

  日期：2017.5.4

  We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.[GRAPHICS].
• Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
  作者：Gaëlle Simon、Christopher Bérubé、Normand Voyer、Daniel Grenier

  DOI：10.1016/j.bmc.2018.11.042

  日期：2019.6

  Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure-activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.
• Basyuk, V. A.; Gromovoi, T. Yu.; Chuiko, A. A., Doklady Chemistry, 1991, vol. 318, # 4-6, p. 147 - 148
  作者：Basyuk, V. A.、Gromovoi, T. Yu.、Chuiko, A. A.、Soloshonok, V. A.、Kukhar, V. P.

  DOI：——

  日期：——
• BASYUK, V. A.;GROMOVOJ, T. YU.;CHUJKO, A. A.;SOLOSHONOK, V. A.;KUXAR, V. +, DOKL. AN CCCP, 318,(1991) N, S. 905-906
  作者：BASYUK, V. A.、GROMOVOJ, T. YU.、CHUJKO, A. A.、SOLOSHONOK, V. A.、KUXAR, V. +

  DOI：——

  日期：——