(3R,6S)-3,6-diisobutylpiperazine-2,5-dione | 16679-66-6

• 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,6S)-3,6-diisobutylpiperazine-2,5-dione
• 英文别名: (3R,6S)-3,6-bis(2-methylpropyl)piperazine-2,5-dione
• CAS: 16679-66-6
• 化学式: C₁₂H₂₂N₂O₂
• 分子量: 226.319
• InChiKey: XWYXUMDVQIOAPR-AOOOYVTPSA-N

物化性质

• 熔点：
  288-289 °C
• 沸点：
  445.2±38.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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,6S)-3,6-diisobutylpiperazine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,5S)-2,5-bis(2-methylpropyl)piperazine
  参考文献：
  名称：

  Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities

  摘要：

  With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.051
• 作为产物：
  描述：

  2-溴-4-甲基戊酰氯 在 sodium hydroxide 、 氨 、 水 作用下， 生成 (3R,6S)-3,6-diisobutylpiperazine-2,5-dione
  参考文献：
  名称：

  Fischer,E.; Koelker, Justus Liebigs Annalen der Chemie, 1907, vol. 354, p. 40,44, 46

  摘要：

  DOI：
• 作为试剂：
  描述：

  反式-查耳酮 在 (3R,6S)-3,6-diisobutylpiperazine-2,5-dione 、 双氧水 、 sodium hydroxide 作用下， 以 正己烷 、 水 为溶剂， 反应 72.5h， 生成 (2S,3R)-2,3-epoxy-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Biomimetic epoxidation in aqueous media catalyzed by cyclic dipeptides

  摘要：

  We have developed a practical epoxidation of electron-deficient enones in aqueous media using cyclic dipeptides as bioinspired green catalyst. Optimizing the reaction conditions in a triphasic system led to efficient conditions providing epoxides with good enantioselectivities. Depending on the catalyst substituent chirality, both enantiomers are obtained. The cyclic rigidity impacts significantly the enantioselectivity.

  DOI：

  10.1080/00397911.2016.1141428

文献信息

• Heterogeneous Catalytic Hydrogenation of Chiral Amino Acid Methyl Esters to Amino Alcohols with Retention of Configuration Over Mg-Modified Cu/ZnO/Al2O3 Catalyst
  作者：Bing Zhan、Shuangshuang Zhang、Jun Yu、Xiuzheng Xiao、Xiaoming Guo、Dongsen Mao、Guanzhong Lu

  DOI：10.1007/s10562-017-2116-3

  日期：2017.8

  hydrogenation of amino acid methyl esters to chiral amino alcohols is an important and fascinating process. The CuZn0.3Mg0.1AlOx catalyst for the synthesis of chiral amino alcohols was prepared by the fractional co-precipitation method in the 50–100 g scale. The effect of the reduction gas on the catalytic activity, and the effects of the reaction conditions (R-p-m/Cat, temperature, reaction time, H2 pressure

  将氨基酸甲酯选择性氢化为手性氨基醇是一个重要且引人入胜的过程。用于合成手性氨基醇的 CuZn0.3Mg0.1AlOx 催化剂是通过分级共沉淀法以 50-100 g 的规模制备的。考察了还原气体对催化活性的影响，以及反应条件（Rpm/Cat、温度、反应时间、H2压力和溶剂）对R-苯基甘氨酸甲酯催化加氢反应（记为Rpm）的影响. 当 Rpm 在乙醇溶剂中在 5 MPa 的 H2 和 80°C 下在该被 H2 还原的催化剂上加氢 10 小时时，获得了 87.7% 的产率，具有~100% ee 值的 R-苯基甘氨醇，其反应活化能（Ea ) 为 36.7 kJ/mol。重复使用16次后，其催化活性几乎没有变化。
• Isolation and structure of flutimide, a novel endonuclease inhibitor of influenza virus
  作者：Otto D. Hensens、Michael A. Goetz、Jerrold M. Liesch、Deborah L. Zink、Susan L. Raghoobar、Gregory L. Helms、Sheo B. Singh

  DOI：10.1016/0040-4039(95)00213-v

  日期：1995.3

  The isolation and structure elucidation of flutimide (1), an inhibitor of flutranscription endonuclease from Delitschia confertaspora, a new species, is reported. The novel natural product is characterized by N-hydroxyimide and exocyclic enamine functionalities.

  据报道，一种新物种Delfitschia confertaspora的一种荧光转录核酸内切酶抑制剂flutimide（1）的分离和结构阐明。该新颖的天然产物的特征在于N-羟基酰亚胺和环外烯胺官能团。
• 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.
• 15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5-dioxopiperazines)
  作者：Hans R. Kricheldorf

  DOI：10.1002/mrc.1270130111

  日期：1980.1

  AbstractVarious cyclodipeptides containing glycine, alanine, leucine, valine, phenylalanine, phenylglycine and sarcosine units were synthesized by cyclization of dipeptide pentachlorophenyl esters. The 13C and natural abundance 15N NMR spectra of these heterocycles were measured in trifluoroacetic acid and compared with the spectra of the corresponding amino acids and polypeptides. The 13C NMR carbonyl signals of all cyclodipeptides show a 1.5–4.0 ppm upfield shift relative to the corresponding polypeptides. The 15N NMR signals show no such consistent relationship. The substituent effects and the neighbouring residue effects observed in the 15N NMR spectra of the cyclodipeptides are different from those of polypeptides, while the one bond NH coupling constant of cis and trans amide groups was almost identical. The nitrogen and the carbonyl signal of the Gly units in cyclo‐Gly‐Phe show an extraordinary downfield shift, reflecting the interaction of the phenyl group with the 2,5‐dioxopiperazine ring.