(S,S)-4-amino-3,5-bis(1-hydroxyethyl)-1,2,4-triazole | 111853-53-3

• 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)-4-amino-3,5-bis(1-hydroxyethyl)-1,2,4-triazole
• 英文别名: (1S)-1-[4-amino-5-[(1S)-1-hydroxyethyl]-1,2,4-triazol-3-yl]ethanol
• CAS: 111853-53-3
• 化学式: C₆H₁₂N₄O₂
• 分子量: 172.187
• InChiKey: JOXDXBMIJJFJMN-IMJSIDKUSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  426.0±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 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：
  97.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  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：
• 作为产物：
  描述：

  L-乳酸 在 肼 作用下， 生成 (S,S)-4-amino-3,5-bis(1-hydroxyethyl)-1,2,4-triazole
  参考文献：
  名称：

  Synthesis of chiral primary amines: diastereoselective alkylation of N-[(1E)-alkylidene]-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amines and N4–Nexocyclic bond cleavage in the resulting 1,2,4-triazol-4-alkylamines

  摘要：

  Enantiomerically pure 3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine 14a and 3,5-bis[(1S)-1-ethoxyethyl]-4H-1,2,4-triazol-4-amine 14b were used as chiral auxiliaries to obtain enantiomerically enriched alpha-aminoacetals, primary alkyl and arylalkyl amines (ee ranging from 40% to 90%). The different stages of the process were imine formation from the corresponding aldehydes, diastereoselective addition of a Grignard reagent, quaternization of the triazole auxiliary and cleavage of the N-4-N-exocylic bond by LiBH4. The mechanism of the cleavage of the N-4-N-exocyclic bond is supported by the use of deuterated metal hydride. The absolute configurations of the new stereogenic centres were established by X-ray analyses of the enantiomerically pure stereomers isolated by semi-preparative liquid chromatography on a chiral support. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.015

文献信息

• Control of bulk homochirality and proton conductivity in isostructural chiral metal–organic frameworks
  作者：Bai-Qiao Song、Da-Qin Chen、Zhenguo Ji、Junhong Tang、Xin-Long Wang、Hong-Ying Zang、Zhong-Min Su

  DOI：10.1039/c6cc07729c

  日期：——

  Two enantiomeric pairs of isostructural homochiral metal–organic frameworks (MOFs) have been synthesized directly from chiral ligands and indirectly from achiral ligandsviaspontaneous resolution combined with cooperative chirality induction, respectively.

  通过手性配体直接合成了两对对映异构同构手性金属-有机框架（MOFs），也通过无手性配体通过自发分辨结合协同手性诱导间接合成。
• [EN] PROCESS FOR THE PREPARATION OF PRIMARY AMINES<br/>[FR] PROCEDE DE PREPARATION D'AMINES PRIMAIRES
  申请人：CLARIANT FRANCE SA

  公开号：WO2004013081A1

  公开（公告）日：2004-02-12

  Process for the preparation of primary amines of formula (I): on enclosed where R3 represents an alkyl, cycloalkyl or aralkyl group, by reaction of a triazolium salt of formula (II): (formula see on enclosed paper version) where R1 and R2 represent hydrogen or an alkyl, aralkyl or aryl group, R4 represents an alkyl or aralkyl group or a residue of an organic polymer functionalized by an alkylating group, and A- represents a halogen, alkylsulphonate, arylsulphonate, alkyl sulphate, hydrogensulphate, hemisulphate, perchlorate or hydroxide, with a hydride, in order to obtain an amine of formula (I), which is isolated, if desired, and intermediates.

  制备式(I)的主要胺的过程：通过将式(II)的三唑盐与氢化物反应（式子见附上的纸张版本），其中R1和R2代表氢或烷基、芳基烷基或芳基，R4代表烷基或芳基烷基或被烷基化基团功能化的有机聚合物残基，A-代表卤素、烷基磺酸盐、芳基磺酸盐、烷基硫酸盐、氢硫酸盐、半硫酸盐、高氯酸盐或氢氧化物，其中R3代表烷基、环烷基或芳基烷基。最终得到式(I)的胺，可隔离，如果需要，还有中间体。
• [EN] PROCESS OF PREPARATION OF OPTICALLY ACTIVE ALPHA AMINOACETALS<br/>[FR] PRÉPARATION D'ALPHA AMINOCÉTALS OPTIQUEMENT ACTIFS
  申请人：CLARIANT SPECIALTY FINE CHEM

  公开号：WO2009106386A1

  公开（公告）日：2009-09-03

  The invention relates to a process for preparing optically active α-aminoacetals by resolution of a racemic mixture or of a mixture of enantiomers via the formation of diastereoisomeric salts, and also novel intermediates in the form of diastereoisomeric salts.

  该发明涉及一种制备光学活性α-氨基缩醛的方法，通过分离外消旋混合物或对映异构体混合物，通过形成二对映异构盐，并且还涉及以二对映异构盐形式存在的新型中间体。
• Protonated amine transport and chiral recognition by 1,2,4-triazole podands and macrocycles
  作者：L. Echegoyen、M.V. Martínez-Díaz、J. de Mendoza、T. Torres、M.J. Vicente-Arana

  DOI：10.1016/s0040-4020(01)88322-8

  日期：——

  Transport of ammonium salts across a bulk liquid membrane with chiral macrocycles and podands containing a 1,2,4-triazole subunit takes place with moderate enantioselectivity. Good transport rates were found for both podands and macrocycles, but chiral recognition was less effective with podands.

  铵盐通过带有1,2,4-三唑亚基的手性大环化合物和手足蛋白在整个液体膜上的运输具有中等的对映选择性。豆荚和大环化合物均具有良好的转运速率，但手足识别对豆荚的有效性较差。
• 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。