(2S)-2-fluoro-2-(tert-butoxycarbonylaminomethyl)-3-phenylpropanoic acid | 1013088-98-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-2-fluoro-2-(tert-butoxycarbonylaminomethyl)-3-phenylpropanoic acid
• 英文别名: (2S)-2-benzyl-2-fluoro-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 1013088-98-6
• 化学式: C₁₅H₂₀FNO₄
• 分子量: 297.327
• InChiKey: RVVNAWJZHVGWIH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-fluoro-2-(tert-butoxycarbonylaminomethyl)-3-phenylpropanoic acid 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三氟乙酸 、 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以95%的产率得到(S)-2-benzyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-fluoropropionic acid
  参考文献：
  名称：

  Enantioselective Synthesis of α-Fluorinated β²-Amino Acids

  摘要：

  A methodology for the enantioselective synthesis of a-fluorinated beta(2)-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective-fluorination and alkylation gave 7 in high diastereomeric excess (> 95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta(2)-amino acids.

  DOI：

  10.1021/ol703045z
• 作为产物：
  描述：

  methyl (S)-2-benzyl-3-((tert-butoxycarbonyl)amino)-2-fluoropropanoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以96%的产率得到(2S)-2-fluoro-2-(tert-butoxycarbonylaminomethyl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of α-Fluorinated β²-Amino Acids

  摘要：

  A methodology for the enantioselective synthesis of a-fluorinated beta(2)-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective-fluorination and alkylation gave 7 in high diastereomeric excess (> 95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta(2)-amino acids.

  DOI：

  10.1021/ol703045z

文献信息

• Enantioselective Synthesis of α-Fluorinated β²-Amino Acids
  作者：Michael K. Edmonds、Florian H. M. Graichen、James Gardiner、Andrew D. Abell

  DOI：10.1021/ol703045z

  日期：2008.3.1

  A methodology for the enantioselective synthesis of a-fluorinated beta(2)-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective-fluorination and alkylation gave 7 in high diastereomeric excess (> 95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta(2)-amino acids.