(1S,1'S)-1,1'-[1-(p-nitrobenzoyl)-1H-1,2,4-triazole-3,5-diyl]-bis(ethane-1,1-diyl) bis(p-nitro-benzoate) | 1220100-15-1

• 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: (1S,1'S)-1,1'-[1-(p-nitrobenzoyl)-1H-1,2,4-triazole-3,5-diyl]-bis(ethane-1,1-diyl) bis(p-nitro-benzoate)
• 英文别名: [(1S)-1-[1-(4-nitrobenzoyl)-5-[(1S)-1-(4-nitrobenzoyl)oxyethyl]-1,2,4-triazol-3-yl]ethyl] 4-nitrobenzoate
• CAS: 1220100-15-1
• 化学式: C₂₇H₂₀N₆O₁₁
• 分子量: 604.489
• InChiKey: NVUOOYGZQZRUFR-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (1S,1'S)-1,1'-[1-(p-nitrobenzoyl)-1H-1,2,4-triazole-3,5-diyl]-bis(ethane-1,1-diyl) bis(p-nitro-benzoate) 在 水 作用下， 以 甲醇 为溶剂， 生成 4-nitrobenzoic acid 1-[5-(1-(4-nitrobenzoyloxy)-ethyl)-2H-1,2,4-triazol-3-yl]-ethyl ester
  参考文献：
  名称：

  Chiral 1,2,4-triazoles: stereoselective acylation and chlorination

  摘要：

  Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3.5-bis-(1-hydroxyethyl)-[ 1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee. depending on the temperature conditions and nature of the reagents Thionyl chloride replaced the hydroxyl groups of (S)-1-[4-amino5-((S)- 1-hydroxy-ethyl)-[1,2,4]-triazol-3-yl]-ethanol 3 stereospecifically with inversion, as confirmed by X-ray analysis, which also revealed unusual crystal structures with asymmetric units comprising three molecules of 4-amino-3,5-bis(R-1-chloroethyl)-1,2,4-triazole 5 and four of 3,5-bis((R)-1-chloroethyl)-1H-1,2,4-triazole 6. (c) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.12.007
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 (S,S)-3,5-bis(1-hydroxyethyl)-1H-1,2,4-triazole 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以50%的产率得到(1S,1'S)-1,1'-[1-(p-nitrobenzoyl)-1H-1,2,4-triazole-3,5-diyl]-bis(ethane-1,1-diyl) bis(p-nitro-benzoate)
  参考文献：
  名称：

  Chiral 1,2,4-triazoles: stereoselective acylation and chlorination

  摘要：

  Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3.5-bis-(1-hydroxyethyl)-[ 1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee. depending on the temperature conditions and nature of the reagents Thionyl chloride replaced the hydroxyl groups of (S)-1-[4-amino5-((S)- 1-hydroxy-ethyl)-[1,2,4]-triazol-3-yl]-ethanol 3 stereospecifically with inversion, as confirmed by X-ray analysis, which also revealed unusual crystal structures with asymmetric units comprising three molecules of 4-amino-3,5-bis(R-1-chloroethyl)-1,2,4-triazole 5 and four of 3,5-bis((R)-1-chloroethyl)-1H-1,2,4-triazole 6. (c) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.12.007

文献信息

• Chiral 1,2,4-triazoles: stereoselective acylation and chlorination
  作者：Alan R. Katritzky、Dmytro Fedoseyenko、Myong S. Kim、Peter J. Steel

  DOI：10.1016/j.tetasy.2009.12.007

  日期：2010.1

  Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3.5-bis-(1-hydroxyethyl)-[ 1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee. depending on the temperature conditions and nature of the reagents Thionyl chloride replaced the hydroxyl groups of (S)-1-[4-amino5-((S)- 1-hydroxy-ethyl)-[1,2,4]-triazol-3-yl]-ethanol 3 stereospecifically with inversion, as confirmed by X-ray analysis, which also revealed unusual crystal structures with asymmetric units comprising three molecules of 4-amino-3,5-bis(R-1-chloroethyl)-1,2,4-triazole 5 and four of 3,5-bis((R)-1-chloroethyl)-1H-1,2,4-triazole 6. (c) 2010 Elsevier Ltd All rights reserved