methyl 3-((2R,5R)-2-hydroxy-5-phenyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-3-yl)propanoate | 1009605-82-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-((2R,5R)-2-hydroxy-5-phenyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-3-yl)propanoate
• 英文别名: methyl 3-[(3R,6R)-6-hydroxy-3-phenyl-6-(trifluoromethyl)-2,3-dihydro-1,4-oxazin-5-yl]propanoate
• CAS: 1009605-82-6
• 化学式: C₁₅H₁₆F₃NO₄
• 分子量: 331.292
• InChiKey: SRVAMLHUIGZWGL-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-((2R,5R)-2-hydroxy-5-phenyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-3-yl)propanoate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 6,6,6-trifluoro-4-((R)-2-hydroxy-1-phenylethylamino)hexane-1,5-diol 、 (4R,5R)-6,6,6-trifluoro-4-((R)-2-hydroxy-1-phenylethylamino)hexane-1,5-diol
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n
• 作为产物：
  描述：

  methyl 3-[(3R)-6-oxo-3-phenyl-2,3-dihydro-1,4-oxazin-5-yl]propanoate 、 (三氟甲基)三甲基硅烷 在 三(二甲氨基)锍二氟三甲基硅酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以74%的产率得到methyl 3-((2R,5R)-2-hydroxy-5-phenyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-3-yl)propanoate
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n

文献信息

• An Efficient Entry to Optically Active <i>anti</i>- and <i>syn</i>-β-Amino-α-trifluoromethyl Alcohols
  作者：Santos Fustero、Laia Albert、José Luis Aceña、Juan F. Sanz-Cervera、Amparo Asensio

  DOI：10.1021/ol702947n

  日期：2008.2.1

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.