4-(5-氟-2-甲氧基-苯基)-4-氧代-丁酸 | 49800-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(5-氟-2-甲氧基-苯基)-4-氧代-丁酸
• 英文名称: 4-(5-Fluoro-2-methoxyphenyl)-4-oxobutanoic acid
• CAS: 49800-56-8
• 化学式: C₁₁H₁₁FO₄
• 分子量: 226.204
• InChiKey: STRZAYFOSFZMGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：

  甲醇 、 4-(5-氟-2-甲氧基-苯基)-4-氧代-丁酸 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoate
  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：

  丁二酸酐 、 对氟苯甲醚 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 4-(5-氟-2-甲氧基-苯基)-4-氧代-丁酸
  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

文献信息

• Enantioselective microbial reduction of substituted acetophenones
  作者：Ramesh N Patel、Animesh Goswami、Linda Chu、Mary Jo Donovan、Venkata Nanduri、Steven Goldberg、Robert Johnston、Prasad J Siva、Brent Nielsen、Junying Fan、WeiXuan He、Zhongping Shi、Kwok Y Wang、Ronald Eiring、Dana Cazzulino、Ambarish Singh、Richard Mueller

  DOI：10.1016/j.tetasy.2004.02.024

  日期：2004.4

  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.