2-acetylfuran-N-[(1R)-1-(methoxymethyl)propyl]-N-(2,2,2-trifluoroethyl)hydrazone | 281192-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-acetylfuran-N-[(1R)-1-(methoxymethyl)propyl]-N-(2,2,2-trifluoroethyl)hydrazone
• CAS: 281192-60-7
• 化学式: C₁₃H₁₉F₃N₂O₂
• 分子量: 292.301
• InChiKey: USVKRRNPFMJPKB-JDAJCMJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.97
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-acetylfuran-N-[(1R)-1-(methoxymethyl)propyl]-N-(2,2,2-trifluoroethyl)hydrazone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以67.3%的产率得到N-[(1S)-1-(furan-2-yl)ethyl]-N'-[(1R)-1-(methoxymethyl)propyl]-N'-(2,2,2-trifluoroethyl)hydrazine
  参考文献：
  名称：

  Diastereoselective LiAlH4 reduction of chiral ketone hydrazones derived from (R)-(–)-2-aminobutan-1-ol

  摘要：

  Various chiral N,N-dialkylhydrazines were prepared in four to five steps from (R)-(-)-2-aminobutan-1-ol 6. They reacted with various prochiral ketones, thus giving the corresponding hydrazones. Reduction of the latter by means of LiAlH4 afforded N,N,N'-trisubstituted hydrazines whose d.e.s were in the range 43-100%. Interestingly, LiAlH4 reduction of the four N-trifluoroethylhydrazones 34 and 38-40 yielded the hydrazines 46 and 48-50, respectively, and with d.e.s = 100% by H-1 and C-13 NMR. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00044-6
• 作为产物：
  描述：

  (2R)-1-methoxy-N-nitroso-N-(2,2,2-trifluoroethyl)butan-2-amine 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 6.0h， 生成 2-acetylfuran-N-[(1R)-1-(methoxymethyl)propyl]-N-(2,2,2-trifluoroethyl)hydrazone
  参考文献：
  名称：

  Diastereoselective LiAlH4 reduction of chiral ketone hydrazones derived from (R)-(–)-2-aminobutan-1-ol

  摘要：

  Various chiral N,N-dialkylhydrazines were prepared in four to five steps from (R)-(-)-2-aminobutan-1-ol 6. They reacted with various prochiral ketones, thus giving the corresponding hydrazones. Reduction of the latter by means of LiAlH4 afforded N,N,N'-trisubstituted hydrazines whose d.e.s were in the range 43-100%. Interestingly, LiAlH4 reduction of the four N-trifluoroethylhydrazones 34 and 38-40 yielded the hydrazines 46 and 48-50, respectively, and with d.e.s = 100% by H-1 and C-13 NMR. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00044-6