2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid | 848949-87-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid
• 英文别名: 2-Benzamido-4-fluoro-4-methylpentanoic acid
• CAS: 848949-87-1
• 化学式: C₁₃H₁₆FNO₃
• 分子量: 253.273
• InChiKey: MIBOOJIVQMLVMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid 在 novozyme-435 、 硫酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-Amino-5,5-dimethyl-dihydro-furan-2-one; compound with sulfuric acid
  参考文献：
  名称：

  An Efficient Chemoenzymatic Approach to (S)-γ-Fluoroleucine Ethyl Ester

  摘要：

  An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of 2-(3-butenyl)azlactone 7b with EtOH to give amide ester (S)-6b in 84% enantiomeric excess. Removal of the N-pentenoyl group with N,N-dibromodimethylhydantoin in the presence of trifluoroacetic acid afforded the titled compound, which was isolated as its hydrogen sulfate salt in 75% yield and > 97% ee.

  DOI：

  10.1021/jo047918j
• 作为产物：
  描述：

  苯甲酰氯 、 ethyl-2-(diphenylmethyleneamino)-4-fluoro-4-methylpentanoate 在 盐酸 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 水 、 四氢呋喃 为溶剂， 生成 2-Benzoylamino-4-fluoro-4-methyl-pentanoic acid
  参考文献：
  名称：

  An Efficient Chemoenzymatic Approach to (S)-γ-Fluoroleucine Ethyl Ester

  摘要：

  An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of 2-(3-butenyl)azlactone 7b with EtOH to give amide ester (S)-6b in 84% enantiomeric excess. Removal of the N-pentenoyl group with N,N-dibromodimethylhydantoin in the presence of trifluoroacetic acid afforded the titled compound, which was isolated as its hydrogen sulfate salt in 75% yield and > 97% ee.

  DOI：

  10.1021/jo047918j

文献信息

• An Efficient Chemoenzymatic Approach to (<i>S</i>)-γ-Fluoroleucine Ethyl Ester
  作者：John Limanto、Ali Shafiee、Paul N. Devine、Veena Upadhyay、Richard A. Desmond、Bruce R. Foster、Donald R. Gauthier、Robert A. Reamer、R. P. Volante

  DOI：10.1021/jo047918j

  日期：2005.3.1

  An asymmetric synthesis of (S)-gamma-fluoroleucine ethyl ester 1 is described. The key transformation involves a lipase-catalyzed dynamic ring-opening of 2-(3-butenyl)azlactone 7b with EtOH to give amide ester (S)-6b in 84% enantiomeric excess. Removal of the N-pentenoyl group with N,N-dibromodimethylhydantoin in the presence of trifluoroacetic acid afforded the titled compound, which was isolated as its hydrogen sulfate salt in 75% yield and > 97% ee.