3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine | 180716-41-0

• 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[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine
• 英文别名: (S,S)-4-amino-3,5-bis(1-methoxyethyl)-1,2,4-triazole；3,5-bis[(1S)-1-methoxyethyl]-1,2,4-triazol-4-amine
• CAS: 180716-41-0
• 化学式: C₈H₁₆N₄O₂
• 分子量: 200.241
• InChiKey: ZRIBEGUYHNMPQQ-WDSKDSINSA-N

物化性质

• 熔点：
  66-70 °C
• 沸点：
  339.8±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine 在 盐酸 、 sodium nitrite 作用下， 反应 1.25h， 以85%的产率得到3,5-bis[(1S)-1-methoxyethyl]-1H-1,2,4-triazole
  参考文献：
  名称：

  Chiral 1,2,4-triazole derivatives as potential synthetic intermediates

  摘要：

  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

  DOI：

  10.1016/0957-4166(96)00197-8
• 作为产物：
  描述：

  (S,S)-4-amino-3,5-bis(1-hydroxyethyl)-1,2,4-triazole 、 对甲苯磺酸甲酯 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.75h， 生成 3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF PRIMARY AMINES
  [FR] PROCEDE DE PREPARATION D'AMINES PRIMAIRES

  摘要：

  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。

  公开号：

  WO2004013081A1

文献信息

• Process for the preparation of primary amines
  申请人：Serradeil Albalat Muriel

  公开号：US20050240059A1

  公开（公告）日：2005-10-27

  Process for the preparation of primary amines of formula (I): where R3 represents an alkyl, cycloalkyl or aralkyl group, by reaction of a triazolium salt of formula (II): 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）的初级胺的过程：其中R3代表烷基，环烷基或芳基烷基团，通过式（II）的三唑盐的反应获得，其中R1和R2代表氢或烷基，芳基烷基或芳基团，R4代表烷基或芳基烷基团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，与氢化物反应，以获得式（I）的胺，如果需要，则分离中间体。
• 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
  作者：Muriel Serradeil-Albalat、Christian Roussel、Nicolas Vanthuyne、Jean-Claude Vallejos、Didier Wilhelm

  DOI：10.1016/j.tetasy.2008.12.015

  日期：2008.12

  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.
• PROCESS FOR THE PREPARATION OF PRIMARY AMINES
  申请人：Clariant (France)

  公开号：EP1527041A1

  公开（公告）日：2005-05-04
• US7220883B2
  申请人：——

  公开号：US7220883B2

  公开（公告）日：2007-05-22