4-(5-fluoro-2-hydroxyphenyl)-4-oxobutyric acid methyl ester | 704909-61-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(5-fluoro-2-hydroxyphenyl)-4-oxobutyric acid methyl ester
• 英文别名: Methyl 4-(5-fluoro-2-hydroxyphenyl)-4-oxobutanoate
• CAS: 704909-61-5
• 化学式: C₁₁H₁₁FO₄
• 分子量: 226.204
• InChiKey: ISDXFYCDDXHTBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-fluoro-2-hydroxyphenyl)-4-oxobutyric acid methyl ester 在 palladium diacetate 、 palladium dihydroxide 盐酸 、 potassium phosphate buffer 、 葡萄糖 、 Pichia methanolica SC 13860 、 1,3-双(二苯基膦)丙烷 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~85.0 ℃ 、413.68 kPa 条件下， 反应 47.0h， 生成 4-[5-Fluoro-2-((S)-1-hydroxy-ethyl)-phenyl]-butyric acid methyl ester
  参考文献：
  名称：

  Enantioselective microbial reduction of substituted acetophenones

  摘要：

  The chiral intermediate (S)-1-(2'-bromo-4'-fluoro phenyl)ethanol 2 was prepared by the enantioselective microbial reduction of 2-bromo-4-fluoro acetophenone 1. Organisms from genus Candida, Hansenula, Pichia, Rhodotorula, Saccharomyces, Sphingomonas and Baker's yeast reduced 1 to 2 in >90% yield and 99% enantiomeric excess (ee). In an alternative approach, the enantioselective microbial reductions of methyl, ethyl, and tert-butyl 4-(2'-acetyl-5'-fluorophenyl) butanoates 3, 5, and 7, respectively, were demonstrated using strains of Candida and Pichia. Reaction yields of 40-53% and ee's of 90-99% were obtained for the corresponding (S)-hydroxy esters 4, 6, and 8. The reductase, which catalyzed the enantioselective reduction of ketoesters was purified to homogeneity from cell extracts of Pichia methanolica SC 13825. It was cloned and expressed in Escherichia coli with recombinant cultures used for the enantioselective reduction of keto methyl ester 3 to the corresponding (S)-hydroxy methyl ester 4. On a preparative scale, a reaction yield of 98% and an ee of 99% was obtained. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.024
• 作为产物：
  描述：

  Methyl 4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以1064 g的产率得到4-(5-fluoro-2-hydroxyphenyl)-4-oxobutyric acid methyl ester
  参考文献：
  名称：

  Enantioselective microbial reduction of substituted acetophenones

  摘要：

  The chiral intermediate (S)-1-(2'-bromo-4'-fluoro phenyl)ethanol 2 was prepared by the enantioselective microbial reduction of 2-bromo-4-fluoro acetophenone 1. Organisms from genus Candida, Hansenula, Pichia, Rhodotorula, Saccharomyces, Sphingomonas and Baker's yeast reduced 1 to 2 in >90% yield and 99% enantiomeric excess (ee). In an alternative approach, the enantioselective microbial reductions of methyl, ethyl, and tert-butyl 4-(2'-acetyl-5'-fluorophenyl) butanoates 3, 5, and 7, respectively, were demonstrated using strains of Candida and Pichia. Reaction yields of 40-53% and ee's of 90-99% were obtained for the corresponding (S)-hydroxy esters 4, 6, and 8. The reductase, which catalyzed the enantioselective reduction of ketoesters was purified to homogeneity from cell extracts of Pichia methanolica SC 13825. It was cloned and expressed in Escherichia coli with recombinant cultures used for the enantioselective reduction of keto methyl ester 3 to the corresponding (S)-hydroxy methyl ester 4. On a preparative scale, a reaction yield of 98% and an ee of 99% was obtained. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.024