methyl (2S)-2-hydroxymethyl-2-fluoro-3-phenylpropanoate | 1013088-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2S)-2-hydroxymethyl-2-fluoro-3-phenylpropanoate
• 英文别名: methyl (2S)-2-benzyl-2-fluoro-3-hydroxypropanoate
• CAS: 1013088-69-1
• 化学式: C₁₁H₁₃FO₃
• 分子量: 212.221
• InChiKey: VKZORJULWOKFIV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-hydroxymethyl-2-fluoro-3-phenylpropanoate 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到methyl (2S)-2-fluoro-2-(toluene-4-sulfonyloxymethyl)-3-phenylpropanoate
  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 (2S)-2-benzyloxymethyl-2-fluoro-3-phenylpropanoate 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以98%的产率得到methyl (2S)-2-hydroxymethyl-2-fluoro-3-phenylpropanoate
  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

• A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides
  作者：Yin Zheng、Suihan Zhang、Kam-Hung Low、Weiwei Zi、Zhongxing Huang

  DOI：10.1021/jacs.1c12404

  日期：2022.2.2

  can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-β-hydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access

  对映体富集的叔烷基卤化物普遍存在于生物活性分子中，可作为通用合成中间体来构建复杂结构。虽然常规获得这些基序通常取决于立体选择性碳-卤素或碳-碳键形成反应，但相比之下，使用卤代和前手性四取代碳的不对称方法在很大程度上难以捉摸。在这里，我们报告了一套具有脯氨醇或哌啶醇衍生的四齿配体的双核锌催化剂可以将大量容易获得的卤代丙二酸酯还原为α-卤代-β-羟基酯。这些多官能化的叔烷基氟化物、氯化物和溴化物被证明是氟化药物类似物和多卤化单萜的有用中间体。
• 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.