cis-(R,R)-3,6-dimethyl-1,4-bis(m-bromophenyl)-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-bis(m-bromophenyl)-2,5-dioxopiperazine
• 英文别名: (3R,6R)-1,4-bis(3-bromophenyl)-3,6-dimethylpiperazine-2,5-dione
• 化学式: C₁₈H₁₆Br₂N₂O₂
• 分子量: 452.145
• InChiKey: AOPLYRSZYIOCQL-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 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-(m-bromophenyl)propanamide 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以57%的产率得到cis-(R,R)-3,6-dimethyl-1,4-bis(m-bromophenyl)-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

• 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.