(S)-dimethyl(1-chloro-1-fluoro-2-oxo-2-phenylethyl)phosphonate | 1306786-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-dimethyl(1-chloro-1-fluoro-2-oxo-2-phenylethyl)phosphonate
• 英文别名: (S)-dimethyl 1-chloro-1-fluoro-2-oxo-2-phenylethylphosphonate；(2S)-2-chloro-2-[dimethoxy(oxido)phosphaniumyl]-2-fluoro-1-phenylethanone
• CAS: 1306786-91-3
• 化学式: C₁₀H₁₁ClFO₄P
• 分子量: 280.62
• InChiKey: COYFRUHKPQFERA-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  膦酸,(2-羰基-2-苯基乙基)-,二甲基酯 在 N-氯代丁二酰亚胺 、 (R)-Spymox 、 copper(II) bis(trifluoromethanesulfonate) 、 N-氟代双苯磺酰胺 作用下， 以 甲苯 为溶剂， 反应 26.0h， 以73%的产率得到(S)-dimethyl(1-chloro-1-fluoro-2-oxo-2-phenylethyl)phosphonate
  参考文献：
  名称：

  Enantioselective gem-Chlorofluorination of Active Methylene Compounds Using a Chiral Spiro Oxazoline Ligand

  摘要：

  Highly enantioselective gem-chlorofluorination of active methylene compounds was carried out by using a copper(II) complex of a chiral spiro pyridyl monooxazoline ligand. This reaction yielded alpha-chloro-alpha-fluoro-beta-keto esters and alpha-chloro-alpha-fluoro-beta-keto phosphonates with up to 92% ee. The resulting dihalo beta-keto ester was converted into various alpha-fluoro-alpha-heteroatom-substituted carbonyl compounds via nucleophilic substitution without loss of optical purity. A fully protected beta-amino acid with a gem-chlorofluoromethylene function was also synthesized.

  DOI：

  10.1021/ol201007e

文献信息

• Enantioselective fluorination of α-chloro-β-keto phosphonates in the presence of chiral palladium complexes
  作者：Saet Byeol Woo、Chang Won Suh、Kwang Oh Koh、Dae Young Kim

  DOI：10.1016/j.tetlet.2013.04.054

  日期：2013.6

  The catalytic enantioselective electrophilic fluorination of α-chloro-β-keto phosphonates promoted by chiral palladium complexes has been developed, allowing facile synthesis of the corresponding α-chloro-α-fluoro-β-keto phosphonates with excellent enantioselectivity (up to 95% ee).

  已开发出由手性钯配合物促进的α-氯-β-酮膦酸酯的催化对映体选择性亲电氟化反应，可以轻松合成具有优异对映选择性（高达95％ee的α-氯-α-氟-β-酮-膦酸酯） ）。
• Enantioselective <i>gem</i>-Chlorofluorination of Active Methylene Compounds Using a Chiral Spiro Oxazoline Ligand
  作者：Kazutaka Shibatomi、Akira Narayama、Yoshinori Soga、Tsubasa Muto、Seiji Iwasa

  DOI：10.1021/ol201007e

  日期：2011.6.3

  Highly enantioselective gem-chlorofluorination of active methylene compounds was carried out by using a copper(II) complex of a chiral spiro pyridyl monooxazoline ligand. This reaction yielded alpha-chloro-alpha-fluoro-beta-keto esters and alpha-chloro-alpha-fluoro-beta-keto phosphonates with up to 92% ee. The resulting dihalo beta-keto ester was converted into various alpha-fluoro-alpha-heteroatom-substituted carbonyl compounds via nucleophilic substitution without loss of optical purity. A fully protected beta-amino acid with a gem-chlorofluoromethylene function was also synthesized.