N-(2,2-dimethoxyethyl)-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine | 1130734-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2,2-dimethoxyethyl)-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine
• CAS: 1130734-50-7
• 化学式: C₁₂H₂₄N₄O₄
• 分子量: 288.347
• InChiKey: GXRBIBVFAPYKEG-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  79.66
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxyethyl)-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine 、 溴甲苯 反应 48.0h， 生成 1-苄基-4-[(2,2-二甲氧基乙基)氨基]-3,5-双[(1S)-1-甲氧基乙基]-4H-1,2,4-三唑-1-溴
  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
• 作为产物：
  描述：

  N-[(1E)-2,2-dimethoxyethylidene]-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以97%的产率得到N-(2,2-dimethoxyethyl)-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-4-amine
  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