methyl (2S,3S)-4,4,4-trifluoro-3-[[(1S)-1-phenylethyl]amino]-2-phenylmethoxybutanoate | 198273-26-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3S)-4,4,4-trifluoro-3-[[(1S)-1-phenylethyl]amino]-2-phenylmethoxybutanoate
• CAS: 198273-26-6
• 化学式: C₂₀H₂₂F₃NO₃
• 分子量: 381.395
• InChiKey: RKUCRFKPMSGVEF-WBAXXEDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 methyl (2S,3S)-4,4,4-trifluoro-3-[[(1S)-1-phenylethyl]amino]-2-phenylmethoxybutanoate 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以72%的产率得到(2S,3S)-3-tert-Butoxycarbonylamino-4,4,4-trifluoro-2-hydroxy-butyric acid methyl ester
  参考文献：
  名称：

  Diastereoselective Synthesis of the Nonracemic Methyl syn-(3-Fluoroalkyl)isoserinates

  摘要：

  Cycloaddition of the (fluoroalkyl)imines 7a-c with the ketene formed in situ from (benzyloxy)acetyl chloride and triethylamine provided stereoselectively cis-(fluoroalkyl)azetidinones 5a-c in moderate yields. The corresponding N-Boc-isoserinates 11a-c and protected synthons 12a-c have been prepared from these azetidinones 5a-c. Cycloaddition of the chiral imine 18 (R-F = CF3) with the same ketene led to the diastereoisomeric azetidinones 19 and 20 with a poor diastereoisomeric excess (10-20%). However, the two diastereoisomers could be easily separated by crystallization and provided enantiomerically pure N-Boc-isoserinates 23 (R,R) and 23 (S,S) after ring opening and debenzylation.

  DOI：

  10.1021/jo971381a
• 作为产物：
  描述：

  (1S)-1-phenyl-N-[(E)-2,2,2-trifluoroethylidene]ethanamine 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl (2S,3S)-4,4,4-trifluoro-3-[[(1S)-1-phenylethyl]amino]-2-phenylmethoxybutanoate
  参考文献：
  名称：

  Diastereoselective Synthesis of the Nonracemic Methyl syn-(3-Fluoroalkyl)isoserinates

  摘要：

  Cycloaddition of the (fluoroalkyl)imines 7a-c with the ketene formed in situ from (benzyloxy)acetyl chloride and triethylamine provided stereoselectively cis-(fluoroalkyl)azetidinones 5a-c in moderate yields. The corresponding N-Boc-isoserinates 11a-c and protected synthons 12a-c have been prepared from these azetidinones 5a-c. Cycloaddition of the chiral imine 18 (R-F = CF3) with the same ketene led to the diastereoisomeric azetidinones 19 and 20 with a poor diastereoisomeric excess (10-20%). However, the two diastereoisomers could be easily separated by crystallization and provided enantiomerically pure N-Boc-isoserinates 23 (R,R) and 23 (S,S) after ring opening and debenzylation.

  DOI：

  10.1021/jo971381a

文献信息

• Diastereoselective Synthesis of the Nonracemic Methyl <i>syn</i>-(3-Fluoroalkyl)isoserinates
  作者：Ahmed Abouabdellah、Jean-Pierre Bégué、Danièle Bonnet-Delpon、Truong Thi Thanh Nga

  DOI：10.1021/jo971381a

  日期：1997.12.1

  Cycloaddition of the (fluoroalkyl)imines 7a-c with the ketene formed in situ from (benzyloxy)acetyl chloride and triethylamine provided stereoselectively cis-(fluoroalkyl)azetidinones 5a-c in moderate yields. The corresponding N-Boc-isoserinates 11a-c and protected synthons 12a-c have been prepared from these azetidinones 5a-c. Cycloaddition of the chiral imine 18 (R-F = CF3) with the same ketene led to the diastereoisomeric azetidinones 19 and 20 with a poor diastereoisomeric excess (10-20%). However, the two diastereoisomers could be easily separated by crystallization and provided enantiomerically pure N-Boc-isoserinates 23 (R,R) and 23 (S,S) after ring opening and debenzylation.