N-benzyloxycarbonyl-(S)-1'-[(5,7)-dinitroindolin-1-yl]-proline | 1161881-23-7

• 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: N-benzyloxycarbonyl-(S)-1'-[(5,7)-dinitroindolin-1-yl]-proline
• 英文别名: benzyl (2S)-2-(5,7-dinitro-2,3-dihydroindole-1-carbonyl)pyrrolidine-1-carboxylate
• CAS: 1161881-23-7
• 化学式: C₂₁H₂₀N₄O₇
• 分子量: 440.412
• InChiKey: WHFAMUNFXLDRFW-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-benzyl 2-(2-bromo-3,5-dinitrophenethylcarbamoyl)pyrrolidine-1-carboxylate 在 potassium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二环己基磷-2'-甲基联苯 作用下， 以 甲苯 、 乙腈 为溶剂， 以88%的产率得到N-benzyloxycarbonyl-(S)-1'-[(5,7)-dinitroindolin-1-yl]-proline
  参考文献：
  名称：

  Preparation of Photoactivable Amino Acid Derivatives

  摘要：

  A range of N-protected-alpha-amino acyl-5,7-dinitroindolines 3a-z were prepared in good yields from commercially available N-protected-alpha-amino acids 1a-z by a two-step sequence of acylation and intramolecular amide N-arylation. Subsequent photochemical acylation of the N-protected-alpha-amino acyl-5,7-dinitroindolines 3e,g,r afforded the corresponding N-protected-alpha-amino acid amides 22e,g,r (77-92%) under mild conditions. All these reactions occurred with complete retention of chirality as evidenced by NMR analysis. This scheme provides an attractive and alternative method to the conventional acylation of alpha-amino acids, especially in cases where the amide bond needs to be formed without the use of a coupling reagent.

  DOI：

  10.1021/jo900442p

文献信息

• Preparation of Photoactivable Amino Acid Derivatives
  作者：Jean-Luc Débieux、Christian G. Bochet

  DOI：10.1021/jo900442p

  日期：2009.6.19

  A range of N-protected-alpha-amino acyl-5,7-dinitroindolines 3a-z were prepared in good yields from commercially available N-protected-alpha-amino acids 1a-z by a two-step sequence of acylation and intramolecular amide N-arylation. Subsequent photochemical acylation of the N-protected-alpha-amino acyl-5,7-dinitroindolines 3e,g,r afforded the corresponding N-protected-alpha-amino acid amides 22e,g,r (77-92%) under mild conditions. All these reactions occurred with complete retention of chirality as evidenced by NMR analysis. This scheme provides an attractive and alternative method to the conventional acylation of alpha-amino acids, especially in cases where the amide bond needs to be formed without the use of a coupling reagent.