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 | 1130734-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 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
• 英文名称: 1-benzyl-4-[(2,2-dimethoxyethyl)amino]-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazol-1-ium bromide
• CAS: 1130734-52-9
• 化学式: Br*C₁₉H₃₁N₄O₄
• 分子量: 459.384
• InChiKey: VRQWHZYEMWWVCM-YYLIZZNMSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  70.65
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  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 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 生成 1-benzyl-3,5-bis[(1S)-1-methoxyethyl]-4H-1,2,4-triazole 、 氨基乙醛缩二甲醇
  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-(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