(2R,3S)-4-(4-fluorophenyl)-2,3-dimethyl-4-oxo-butyric acid | 946007-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-4-(4-fluorophenyl)-2,3-dimethyl-4-oxo-butyric acid
• 英文别名: (2R,3S)-4-(4-fluorophenyl)-2,3-dimethyl-4-oxobutanoic acid
• CAS: 946007-88-1
• 化学式: C₁₂H₁₃FO₃
• 分子量: 224.232
• InChiKey: FRSRTZQRGUOIHK-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-4-(4-fluorophenyl)-2,3-dimethyl-4-oxo-butyric acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 、 苯 为溶剂， 生成
  参考文献：
  名称：

  Ligand differentiated complementary Rh-catalyst systems for the enantioselective desymmetrization of meso-cyclic anhydrides

  摘要：

  Two distinct systems for the rhodium-catalyzed enantioselective desymmetrization of meso-cyclic anhydrides have been developed. Each system has been optimized and are compatible with the use of in situ prepared organozinc reagents. Rhodium/PHOX species efficiently catalyze the addition of alkyi nucleophiles to glutaric anhydrides, while system is effective in the enantioselective arylation of succinic and glutaric anhydrides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.075
• 作为产物：
  描述：

  对溴氟苯 、 meso-2,3-dimethylsuccinic anhydride 在 正丁基锂 、 zinc trifluoromethanesulfonate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (3AR,8AR)-(-)-(2,2-二甲基-4,4,8,8-四苯基-四氢-[1,3]二氧并[4,5-E][1,3,2]二氧磷-6-YL)二甲胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (2S,3R)-4-(4-fluorophenyl)-2,3-dimethyl-4-oxo-butyric acid 、 (2R,3S)-4-(4-fluorophenyl)-2,3-dimethyl-4-oxo-butyric acid
  参考文献：
  名称：

  Ligand differentiated complementary Rh-catalyst systems for the enantioselective desymmetrization of meso-cyclic anhydrides

  摘要：

  Two distinct systems for the rhodium-catalyzed enantioselective desymmetrization of meso-cyclic anhydrides have been developed. Each system has been optimized and are compatible with the use of in situ prepared organozinc reagents. Rhodium/PHOX species efficiently catalyze the addition of alkyi nucleophiles to glutaric anhydrides, while system is effective in the enantioselective arylation of succinic and glutaric anhydrides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.075

文献信息

• A Concise Synthesis of Eupomatilones 4, 6, and 7 by Rhodium-Catalyzed Enantioselective Desymmetrization of Cyclicmeso Anhydrides with Organozinc Reagents Generated In Situ
  作者：Jeffrey B. Johnson、Eric A. Bercot、Catherine M. Williams、Tomislav Rovis

  DOI：10.1002/anie.200700816

  日期：2007.6.11