3,5-bis-((R)-1-chloroethyl)-1H-[1,2,4]triazole | 1220100-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-bis-((R)-1-chloroethyl)-1H-[1,2,4]triazole
• 英文别名: 3,5-bis[(1R)-1-chloroethyl]-1H-1,2,4-triazole
• CAS: 1220100-11-7
• 化学式: C₆H₉Cl₂N₃
• 分子量: 194.064
• InChiKey: NEXYHAPKUCSMLC-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-bis-((R)-1-chloroethyl)-1H-[1,2,4]triazole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 3,5-bis-(1-chloroethyl)-1H-[1,2,4]triazole
  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：

  (R,R)-4-amino-3,5-bis(1-chloroethyl)-1,2,4-triazole 在 盐酸 、 sodium nitrite 、 碳酸氢钠 作用下， 以 水 为溶剂， 以70%的产率得到3,5-bis-((R)-1-chloroethyl)-1H-[1,2,4]triazole
  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