(E)-N-[3,5-bis[(1S)-1-methoxyethyl]-1,2,4-triazol-4-yl]-1-(4-chlorophenyl)methanimine | 180857-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-[3,5-bis[(1S)-1-methoxyethyl]-1,2,4-triazol-4-yl]-1-(4-chlorophenyl)methanimine
• CAS: 180857-99-2
• 化学式: C₁₅H₁₉ClN₄O₂
• 分子量: 322.794
• InChiKey: ZOKGGBCEWDXFTE-WRKDVHLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苄基溴化镁 、 (E)-N-[3,5-bis[(1S)-1-methoxyethyl]-1,2,4-triazol-4-yl]-1-(4-chlorophenyl)methanimine 以 四氢呋喃 、 甲苯 为溶剂， 以69%的产率得到N-[(1S)-1-(4-chlorophenyl)-2-phenylethyl]-3,5-bis[(1S)-1-methoxyethyl]-1,2,4-triazol-4-amine
  参考文献：
  名称：

  Synthesis and highly diastereoselective alkylation of chiral N-[(S,S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines

  摘要：

  (S,S)-4-Amino-35-bis(1-hydroxyethyl)-1,2,4-triazole 2 (SAT) (from (S)-lactic acid and hydrazine hydrate) reacted with substituted benzaldehydes 6 to afford N-[(S,S)-3,5-bis(1-hydroxyethyl)-1,2,4-triazol-4-yl]arylimines 3 in excellent yield. Protection of the hydroxyl groups in compounds 3 was accomplished using methyl tosylate under mild conditions to give N-[(S, S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines 4 in very high yield. Subsequent reactions of 4 with Grignard reagents afforded compounds 5 with good to excellent diastereoselectivities in good yield. (C) 1986 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00196-6
• 作为产物：
  描述：

  (S,S)-4-amino-3,5-bis(1-hydroxyethyl)-1,2,4-triazole 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 12.17h， 生成 (E)-N-[3,5-bis[(1S)-1-methoxyethyl]-1,2,4-triazol-4-yl]-1-(4-chlorophenyl)methanimine
  参考文献：
  名称：

  Synthesis and highly diastereoselective alkylation of chiral N-[(S,S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines

  摘要：

  (S,S)-4-Amino-35-bis(1-hydroxyethyl)-1,2,4-triazole 2 (SAT) (from (S)-lactic acid and hydrazine hydrate) reacted with substituted benzaldehydes 6 to afford N-[(S,S)-3,5-bis(1-hydroxyethyl)-1,2,4-triazol-4-yl]arylimines 3 in excellent yield. Protection of the hydroxyl groups in compounds 3 was accomplished using methyl tosylate under mild conditions to give N-[(S, S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines 4 in very high yield. Subsequent reactions of 4 with Grignard reagents afforded compounds 5 with good to excellent diastereoselectivities in good yield. (C) 1986 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00196-6

文献信息

• Synthesis and highly diastereoselective alkylation of chiral N-[(S,S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines
  作者：Alan R. Katrizky、Saad R. El-Zemity、Peter Leeming、Chris M. Hartshorn、Peter J. Steel

  DOI：10.1016/0957-4166(96)00196-6

  日期：1996.6

  (S,S)-4-Amino-35-bis(1-hydroxyethyl)-1,2,4-triazole 2 (SAT) (from (S)-lactic acid and hydrazine hydrate) reacted with substituted benzaldehydes 6 to afford N-[(S,S)-3,5-bis(1-hydroxyethyl)-1,2,4-triazol-4-yl]arylimines 3 in excellent yield. Protection of the hydroxyl groups in compounds 3 was accomplished using methyl tosylate under mild conditions to give N-[(S, S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines 4 in very high yield. Subsequent reactions of 4 with Grignard reagents afforded compounds 5 with good to excellent diastereoselectivities in good yield. (C) 1986 Elsevier Science Ltd