(R)-t-butyl 2-fluoro-3-oxo-3-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate | 1306787-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-t-butyl 2-fluoro-3-oxo-3-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate
• 英文别名: tert-butyl (2R)-2-fluoro-3-oxo-3-phenyl-2-(4-phenyltriazol-1-yl)propanoate
• CAS: 1306787-00-7
• 化学式: C₂₁H₂₀FN₃O₃
• 分子量: 381.407
• InChiKey: XOPIKVQQPANNRO-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 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 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 (R)-Spymox 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 、 苯 为溶剂， 反应 11.5h， 生成 (R)-t-butyl 2-fluoro-3-oxo-3-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoate
  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.