cis-(R,R)-3,6-dimethyl-1,4-diphenyl-2,5-dioxopiperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: cis-(R,R)-3,6-dimethyl-1,4-diphenyl-2,5-dioxopiperazine
• 英文别名: cis-1,4-diphenyl-3,6-dimethyl-2,5-dioxopiperazine；(3R,6R)-3,6-dimethyl-1,4-diphenylpiperazine-2,5-dione
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: ZXSTZXXZIJVOIN-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-bromo-N-phenylpropanamide 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以51%的产率得到cis-(R,R)-3,6-dimethyl-1,4-diphenyl-2,5-dioxopiperazine
  参考文献：
  名称：

  Stereoselective Synthesis of N,N‘-Diaryl-2,5-dioxopiperazines from Homochiral or Racemic 2-Bromopropananilides

  摘要：

  N,N'-Diaryl-2,5-dioxopiperazines 8 and 9, related to the amino acid alanine, are easily obtained by self-cyclocoupling of 2-bromopropananilides 7. The cis-(R,R) or cis-(S,S)/trans-(R,S) distribution is controlled, to varying extents, by starting either from a single enantiomer or racemate and by the promoter, aryl substituent, and solvent. H-1 NMR spectra of the members of six diastereomeric couples and X-ray structures of representative products are reported.

  DOI：

  10.1021/jo9511051

文献信息

• Electrochemical and stereochemical investigation on the mechanism of the decay of 2-halo amide anions. The intermediacy of aziridinones
  作者：Flavio Maran

  DOI：10.1021/ja00068a012

  日期：1993.7

  2-Halo amide anions can be generated by electroreduction of the corresponding NH-protic 2-halo amides through the self-protonation mechanism. Such anions are labile species whose decay, in the case of 2-bromo amide anions, competes with their electroreduction in the voltammetric time scale. Using the appropriate voltammetric treatment, the first-order rate constant of the decay has been determined for a series of representative 2-bromo amides. The lability orders point to an S(N)2-type intramolecular substitution of bromine and thus to the formation of a three-membered ring. Stereochemical information on the decay has been gained using a chiral nonracemic 2-bromopropanamide, an amine nucleophile, and DMF as the solvent. The direct substitution by the amine proceeds by an S(N)2 reaction, as witnessed by inversion of configuration at the alpha-carbon and voltammetric analysis. Conversely, when the reaction is triggered by electroreduction, the decay of the 2-bromo amide anion eventually leads to the formation of the retention product 2-amino amide together with other optically active products, namely two diastereomeric oxazolidin-4-ones, arising by cyclocondensation with DMF, and cis-2,5-dioxopiperazine. Analysis of the electrochemical and stereochemical results indicates that the mechanism of the base-promoted reactions of 2-halo amides proceeds through the transient formation of the corresponding aziridinone, independently of the fact that the latter is isolable or not. The formation of the aziridinone takes place by concerted intramolecular nucleophilic substitution of bromide ion within the 2-halo amide anion. The transient aziridinone behaves not only as the product-determining intermediate but also as a species capable of reacting with suitable partners under remarkable enantioselectivity control.
• Cavicchioni, Giorgio; Scrimin, Paolo; Veronese, Augusto C., Journal of the Chemical Society. Perkin transactions I, 1982, # 12, p. 2969 - 2972
  作者：Cavicchioni, Giorgio、Scrimin, Paolo、Veronese, Augusto C.、Balboni, Gianfranco、D'Angeli, Ferruccio

  DOI：——

  日期：——
• CAVICCHIONI, G.;SCRIMIN, P.;VERONESE, A. C.;BALBONI, G.;DANGELI, F., J. CHEM. SOC. PERKIN TRANS., 1982, N 12, 2969-2972
  作者：CAVICCHIONI, G.、SCRIMIN, P.、VERONESE, A. C.、BALBONI, G.、DANGELI, F.

  DOI：——

  日期：——
• Stereoselective Synthesis of <i>N</i>,<i>N</i>‘-Diaryl-2,5-dioxopiperazines from Homochiral or Racemic 2-Bromopropananilides
  作者：Ferruccio D'Angeli、Paolo Marchetti、Riccardo Rondanin、Valerio Bertolasi

  DOI：10.1021/jo9511051

  日期：1996.1.1

  N,N'-Diaryl-2,5-dioxopiperazines 8 and 9, related to the amino acid alanine, are easily obtained by self-cyclocoupling of 2-bromopropananilides 7. The cis-(R,R) or cis-(S,S)/trans-(R,S) distribution is controlled, to varying extents, by starting either from a single enantiomer or racemate and by the promoter, aryl substituent, and solvent. H-1 NMR spectra of the members of six diastereomeric couples and X-ray structures of representative products are reported.