(S)-dimethyl 1-chloro-1-fluoro-2-oxo-2-(thiophen-2-yl)ethylphosphonate | 1306786-96-8

• 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-(thiophen-2-yl)ethylphosphonate
• 英文别名: (2S)-2-chloro-2-dimethoxyphosphoryl-2-fluoro-1-thiophen-2-ylethanone
• CAS: 1306786-96-8
• 化学式: C₈H₉ClFO₄PS
• 分子量: 286.648
• InChiKey: ARFZPRIZBNKAQN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2-oxo-2-thien-2-yl-ethyl)phosphonic acid dimethyl ester 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 72.0h， 生成 、 (S)-dimethyl 1-chloro-1-fluoro-2-oxo-2-(thiophen-2-yl)ethylphosphonate 、 (R)-dimethyl 1-chloro-1-fluoro-2-oxo-2-(thiophen-2-yl)ethylphosphonate
  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 <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.