[(1R,2R)-2-chloro-2-fluoro-3-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3-oxo-1-phenylpropyl] naphthalene-2-carboxylate | 1306787-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(1R,2R)-2-chloro-2-fluoro-3-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3-oxo-1-phenylpropyl] naphthalene-2-carboxylate
• CAS: 1306787-16-5
• 化学式: C₃₀H₃₂ClFO₄
• 分子量: 511.033
• InChiKey: FKXAUDGUTPSYHJ-QMSAFVIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl 3-oxo-3-phenylpropanoate 在 4-二甲氨基吡啶 、 2,2'-联吡啶 、 N-氯代丁二酰亚胺 、 (R)-Spymox 、 copper(II) bis(trifluoromethanesulfonate) 、 N-氟代双苯磺酰胺 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 11.0h， 生成 [(1R,2R)-2-chloro-2-fluoro-3-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3-oxo-1-phenylpropyl] naphthalene-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

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.