(S,S)-3,5-bis(1-hydroxyethyl)-1H-1,2,4-triazole | 111853-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S,S)-3,5-bis(1-hydroxyethyl)-1H-1,2,4-triazole
• 英文别名: (S,S)-3,5-bis(1-hydroxyethyl)-1,2,4-triazole；(1S)-1-[3-[(1S)-1-hydroxyethyl]-1H-1,2,4-triazol-5-yl]ethanol
• CAS: 111853-55-5
• 化学式: C₆H₁₁N₃O₂
• 分子量: 157.172
• InChiKey: QDNXWRJMKKTXMG-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 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：
  82
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,S)-3,5-bis(1-hydroxyethyl)-1H-1,2,4-triazole 在 potassium permanganate 作用下， 以 水 为溶剂， 反应 1.0h， 以75%的产率得到potassium 3,5-diacetyl-1H-1,2,4-triazole
  参考文献：
  名称：

  De Mendoza; Ontoria; Ortega, Synthesis, 1992, # 4, p. 398 - 402

  摘要：

  DOI：
• 作为产物：
  描述：

  (S,S)-4-amino-3,5-bis(1-hydroxyethyl)-1,2,4-triazole 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以92%的产率得到(S,S)-3,5-bis(1-hydroxyethyl)-1H-1,2,4-triazole
  参考文献：
  名称：

  Alonso, Jose M.; Martin, M. Rosario; Mendoza, Javier de, Heterocycles, 1987, vol. 26, # 4, p. 989 - 1000

  摘要：

  DOI：

文献信息

• Synthesis of Optically Active Macrocycles Containing Two 1,2,4-Triazole Subunits
  作者：M. Victoria Martínez-Díaz、Javier de Mendoza、Tomás Torres

  DOI：10.1055/s-1994-25644

  日期：——

  The stepwise synthesis of novel lipophilic, optically active macrocyclic crown ethers (S,S,S,S)-5, 6, 8 and 9, with four chiral centers of the same configuration and two 1,2,4-triazole subunits, starting from readily accessible chiral 3,5-disubstituted 1,2,4-triazoles (S,S)-2 is reported.

  报告从容易获得的手性 3,5-二取代 1,2,4-三唑 (S,S)-2 开始，逐步合成了具有四个相同构型手性中心和两个 1,2,4-三唑亚基的新型亲脂性光学活性大环冠醚 (S,S,S,S)-5、6、8 和 9。
• Chiral 1,2,4-triazole derivatives as potential synthetic intermediates
  作者：Alan R. Katritzky、Jin Wang、Peter Leeming、Peter J. Steel

  DOI：10.1016/0957-4166(96)00197-8

  日期：1996.6

  The potential of (S,S)-3,5-bis(alpha-trimethylsilyloxyethyl)-1,2,4-triazole 3 and (S,S)-3,5-bis(alpha-methoxyethyl)-1,2,4-triazole 9 as chiral synthetic intermediates has been investigated. Reaction of the chiral triazole 3 with ethyl 2-bromopropionate and subsequent treatment with LDA followed by quenching with an electrophile gave either esters 5 or lactones 6&7 in good yields with generally excellent diastereoselectivities. (C) 1996 Elsevier Science Ltd
• Alonso, Jose M.; Martin, M. Rosario; Mendoza, Javier de, Heterocycles, 1987, vol. 26, # 4, p. 989 - 1000
  作者：Alonso, Jose M.、Martin, M. Rosario、Mendoza, Javier de、Torres, Tomas、Elguero, Jose

  DOI：——

  日期：——
• ALONSO, J. M.;MARTIN, M. R.;DE, MENDOZA J.;TORRES, T., HETEROCYCLES, 26,(1987) N 4, 989-1000
  作者：ALONSO, J. M.、MARTIN, M. R.、DE, MENDOZA J.、TORRES, T.

  DOI：——

  日期：——
• 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