(E)-ethyl 2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoate | 164857-19-6

• 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: (E)-ethyl 2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoate
• 英文别名: ethyl (E)-4-fluoro-3-(3-methoxyphenyl)-2-[(2,2,2-trifluoroacetyl)amino]but-3-enoate
• CAS: 164857-19-6
• 化学式: C₁₅H₁₅F₄NO₄
• 分子量: 349.282
• InChiKey: OOOWEJFYRCZSDS-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoate 在 乙酸铵 、 α-chymotropsin 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 R-(E)-ethyl-2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoate
  参考文献：
  名称：

  (E) and (Z)-β-fluoromethylene-m-tyrosines: Resolution and determination of configuration

  摘要：

  The geometrical isomers of beta-fluoromethylene-m-tyrosine (E and Z) were prepared and the R and S enantiomers of the biologically active (E)-isomer were separated with an enantiomeric excess >95% by the kinetic resolution of the racemic mixture using the enzyme alpha-chymotrypsin. The enantiomers of the (Z)-isomer were obtained by an acid catalyzed isomerization reaction. The absolute configurations of the isolated enantiomers were determined based on their CD spectral characteristics and chiral HPLC behavior. The R and S enantiomers of (E)-beta-fluoromethylene-m-tyrosine were also analyzed by single crystal X-ray crystallography.

  DOI：

  10.1016/0957-4166(95)00036-o
• 作为产物：
  描述：

  ethyl 2-amino-3-(3-methoxyphenyl)-4-fluoro-butenoate 、 三氟乙酸酐 反应 2.0h， 以61%的产率得到(E)-ethyl 2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoate
  参考文献：
  名称：

  (E) and (Z)-β-fluoromethylene-m-tyrosines: Resolution and determination of configuration

  摘要：

  The geometrical isomers of beta-fluoromethylene-m-tyrosine (E and Z) were prepared and the R and S enantiomers of the biologically active (E)-isomer were separated with an enantiomeric excess >95% by the kinetic resolution of the racemic mixture using the enzyme alpha-chymotrypsin. The enantiomers of the (Z)-isomer were obtained by an acid catalyzed isomerization reaction. The absolute configurations of the isolated enantiomers were determined based on their CD spectral characteristics and chiral HPLC behavior. The R and S enantiomers of (E)-beta-fluoromethylene-m-tyrosine were also analyzed by single crystal X-ray crystallography.

  DOI：

  10.1016/0957-4166(95)00036-o

文献信息

• (E) and (Z)-β-fluoromethylene-m-tyrosines: Resolution and determination of configuration
  作者：Goran Laćan、N Satyamurthy、Jorge R Barrio

  DOI：10.1016/0957-4166(95)00036-o

  日期：1995.2

  The geometrical isomers of beta-fluoromethylene-m-tyrosine (E and Z) were prepared and the R and S enantiomers of the biologically active (E)-isomer were separated with an enantiomeric excess >95% by the kinetic resolution of the racemic mixture using the enzyme alpha-chymotrypsin. The enantiomers of the (Z)-isomer were obtained by an acid catalyzed isomerization reaction. The absolute configurations of the isolated enantiomers were determined based on their CD spectral characteristics and chiral HPLC behavior. The R and S enantiomers of (E)-beta-fluoromethylene-m-tyrosine were also analyzed by single crystal X-ray crystallography.