t-butyl 2-chloro-2-fluoro-3-hydroxy-3-phenylpropanoate | 1306787-02-9

• 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: t-butyl 2-chloro-2-fluoro-3-hydroxy-3-phenylpropanoate
• 英文别名: tert-butyl (2R,3R)-2-chloro-2-fluoro-3-hydroxy-3-phenylpropanoate
• CAS: 1306787-02-9
• 化学式: C₁₃H₁₆ClFO₃
• 分子量: 274.72
• InChiKey: NXMHBNZGJYOCCK-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  t-butyl 2-chloro-2-fluoro-3-hydroxy-3-phenylpropanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 生成 t-butyl 2-fluoro-3-phenyloxirane-2-carboxylate
  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
• 作为产物：
  描述：

  3-氧代-3-苯基丙酸叔丁酯 在 N-氯代丁二酰亚胺 、 (R)-Spymox 、 copper(II) bis(trifluoromethanesulfonate) 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 7.0h， 生成 t-butyl 2-chloro-2-fluoro-3-hydroxy-3-phenylpropanoate 、 t-butyl 2-chloro-2-fluoro-3-hydroxy-3-phenylpropanoate
  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.