Ethyl 2-<(trifluoroacetyl)amino>-3-(3-hydroxyphenyl)-4-fluoro-3-butenoate | 160848-41-9

• 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: Ethyl 2-<(trifluoroacetyl)amino>-3-(3-hydroxyphenyl)-4-fluoro-3-butenoate
• 英文别名: ethyl (E)-4-fluoro-3-(3-hydroxyphenyl)-2-[(2,2,2-trifluoroacetyl)amino]but-3-enoate
• CAS: 160848-41-9
• 化学式: C₁₄H₁₃F₄NO₄
• 分子量: 335.255
• InChiKey: FHMZDVMNSKNHJP-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 Ethyl 2-<(trifluoroacetyl)amino>-3-(3-hydroxyphenyl)-4-fluoro-3-butenoate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以55%的产率得到Ethyl 2-<(trifluoroacetyl)amino>-3-<<3-(tert-butoxycarbonyl)oxy>phenyl>-4-fluoro-3-butenoate
  参考文献：
  名称：

  Fluorination of (E)-.beta.-(Fluoromethylene)-m-Tyrosine: Regioselective Synthesis of 4-Fluoro-(E)-.beta.-(Fluoromethylene)-m-Tyrosine

  摘要：

  Fluorination of (R)- and (S)-(E)-beta-(fluoromethylene)-m-tyrosine (1) by acetyl hypofluorite yielded a mixture of the corresponding 2-fluoro- (2a), 6-fluaro- (2b), 4-fluoro- (2c), and 2,6-difluoro- (2d) derivatives along with a pair of diastereomeric products of addition across the vinylic double bond. A regioselective synthesis of 4-fluoro-(E)-beta-(fluoromethylene)-m-tyrosine has also been developed based on a fluorodestannylation reaction with elemental fluorine followed by acid hydrolysis. This reaction sequence yielded minor byproducts, namely, 4-fluoro-(Z)-beta-(fluoromethylene)-m-tyrosine (II), 4,6-difluoro- and 2,4-difluoro-(E)-beta-(fluoromethylene)-m-tyrosines (12a and 12b). All these products were completely separated by semipreparative HPLC and fully characterized by NMR and mass spectroscopy. Single crystal X-ray crystallographic analyses of 2-fluoro-, 4-fluoro-, and 6-fluoro-(E)-beta-(fluoromethylene)-m-tyrosines unequivocally established the structures of these amino acids.

  DOI：

  10.1021/jo00106a038
• 作为产物：
  描述：

  (E)-β-(Fluoromethylene)-m-tyrosine 在 盐酸 作用下， 反应 10.0h， 生成 Ethyl 2-<(trifluoroacetyl)amino>-3-(3-hydroxyphenyl)-4-fluoro-3-butenoate
  参考文献：
  名称：

  Fluorination of (E)-.beta.-(Fluoromethylene)-m-Tyrosine: Regioselective Synthesis of 4-Fluoro-(E)-.beta.-(Fluoromethylene)-m-Tyrosine

  摘要：

  Fluorination of (R)- and (S)-(E)-beta-(fluoromethylene)-m-tyrosine (1) by acetyl hypofluorite yielded a mixture of the corresponding 2-fluoro- (2a), 6-fluaro- (2b), 4-fluoro- (2c), and 2,6-difluoro- (2d) derivatives along with a pair of diastereomeric products of addition across the vinylic double bond. A regioselective synthesis of 4-fluoro-(E)-beta-(fluoromethylene)-m-tyrosine has also been developed based on a fluorodestannylation reaction with elemental fluorine followed by acid hydrolysis. This reaction sequence yielded minor byproducts, namely, 4-fluoro-(Z)-beta-(fluoromethylene)-m-tyrosine (II), 4,6-difluoro- and 2,4-difluoro-(E)-beta-(fluoromethylene)-m-tyrosines (12a and 12b). All these products were completely separated by semipreparative HPLC and fully characterized by NMR and mass spectroscopy. Single crystal X-ray crystallographic analyses of 2-fluoro-, 4-fluoro-, and 6-fluoro-(E)-beta-(fluoromethylene)-m-tyrosines unequivocally established the structures of these amino acids.

  DOI：

  10.1021/jo00106a038

文献信息

• Fluorination of (E)-.beta.-(Fluoromethylene)-m-Tyrosine: Regioselective Synthesis of 4-Fluoro-(E)-.beta.-(Fluoromethylene)-m-Tyrosine
  作者：Goran Lacan、N. Satyamurthy、Jorge R. Barrio

  DOI：10.1021/jo00106a038

  日期：1995.1

  Fluorination of (R)- and (S)-(E)-beta-(fluoromethylene)-m-tyrosine (1) by acetyl hypofluorite yielded a mixture of the corresponding 2-fluoro- (2a), 6-fluaro- (2b), 4-fluoro- (2c), and 2,6-difluoro- (2d) derivatives along with a pair of diastereomeric products of addition across the vinylic double bond. A regioselective synthesis of 4-fluoro-(E)-beta-(fluoromethylene)-m-tyrosine has also been developed based on a fluorodestannylation reaction with elemental fluorine followed by acid hydrolysis. This reaction sequence yielded minor byproducts, namely, 4-fluoro-(Z)-beta-(fluoromethylene)-m-tyrosine (II), 4,6-difluoro- and 2,4-difluoro-(E)-beta-(fluoromethylene)-m-tyrosines (12a and 12b). All these products were completely separated by semipreparative HPLC and fully characterized by NMR and mass spectroscopy. Single crystal X-ray crystallographic analyses of 2-fluoro-, 4-fluoro-, and 6-fluoro-(E)-beta-(fluoromethylene)-m-tyrosines unequivocally established the structures of these amino acids.