(S)-2-Bromo-N-(m-bromophenyl)propanamide | 40781-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-Bromo-N-(m-bromophenyl)propanamide
• 英文别名: L-α-Bromopropionsaeure-(m-bromoanilid)；L-(-)-α,3'-Dibrompropionanilid；Propanamide, 2-bromo-N-(3-bromophenyl)-, (S)-；(2S)-2-bromo-N-(3-bromophenyl)propanamide
• CAS: 40781-54-2
• 化学式: C₉H₉Br₂NO
• 分子量: 306.985
• InChiKey: JNYINQOGFZYCJN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (S)-2-bromopropionyl chloride 、 间溴苯胺 以 苯 为溶剂， 生成 (S)-2-Bromo-N-(m-bromophenyl)propanamide
  参考文献：
  名称：

  Snatzke,G.; El-Abadelah,M.M., Chemische Berichte, 1973, vol. 106, p. 2072 - 2075

  摘要：

  DOI：

文献信息

• Stereoselective Substitution in 2-Bromo Amides in the Presence of Ag+ or Ag2O
  作者：Ferruccio D'Angeli、Paolo Marchetti、Valerio Bertolasi

  DOI：10.1021/jo00118a017

  日期：1995.6

  Bromine displacement by a primary, secondary, or tertiary amine, or methanol, in chiral nonracemic (S)-2-bromopropanamides 1 occurs with high yields and stereo selectivity. Soluble Ag+ promotes inversion, and solid Ag2O promotes retention of configuration. However, in the case of Et(3)N, Ag+ promotes retention. With the hindered 2-bromo-2-methylbutanamide 5, the displacement by a primary or secondary amine or methanol occurs only in the presence of Ag2O, possibly with retention of configuration.