(S)-(E)-β-(Fluoromethylene)-m-tyrosine | 99685-71-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-(E)-β-(Fluoromethylene)-m-tyrosine
• 英文别名: S-(E)-β-fluoromethylene-m-tyrosine；beta-Fluoromethylene-3-tyrosine；(E,2S)-2-amino-4-fluoro-3-(3-hydroxyphenyl)but-3-enoic acid
• CAS: 99685-71-9
• 化学式: C₁₀H₁₀FNO₃
• 分子量: 211.193
• InChiKey: LAUWCWCSEOWJMQ-QRJSTWQJSA-N

物化性质

• 沸点：
  447.3±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(E)-β-(Fluoromethylene)-m-tyrosine 、 氟乙酰 以22%的产率得到
  参考文献：
  名称：

  DEJESUS, O. T.;MURALI, D.;CHEN, C. -A.;SUNDERLAND, J. J.;WEILER, M.;NICKL+, J. LABELL. COMPOUNDS AND RADIOPHARM, 30,(1991) N(!), C. 272-273

  摘要：

  DOI：
• 作为产物：
  描述：

  S-(E)-2-trifluoroacetylamino-3-(3-methoxyphenyl)-4-fluoro-3-butenoic acid 在 氢溴酸 作用下， 反应 0.5h， 以95%的产率得到(S)-(E)-β-(Fluoromethylene)-m-tyrosine
  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

• Prodrugs of antidepressants and their use for treating depressions
  申请人：——

  公开号：US20040242594A1

  公开（公告）日：2004-12-02

  This invention relates to prodrugs of antidepressants and the use of these prodrugs in a method for therapy and to pharmaceutical compositions comprising the prodrugs of the invention.

  本发明涉及抗抑郁药的前药及其在治疗方法中的使用，以及包含本发明的前药的制药组合物。
• 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.
• PRODRUGS OF ANTIDEPRESSANTS AND THEIR USE FOR TREATING DEPRESSIONS
  申请人：NeuroSearch A/S

  公开号：EP1448512A1

  公开（公告）日：2004-08-25
• METHODS AND COMPOSITIONS FOR TREATING PAIN
  申请人：Apkarian Technologies LLC

  公开号：EP3946302A1

  公开（公告）日：2022-02-09
• [EN] PRODRUGS OF ANTIDEPRESSANTS AND THEIR USE FOR TREATING DEPRESSIONS<br/>[FR] PROMEDICAMENTS D'ANTIDEPRESSEURS ET UTILISATION ASSOCIEE DANS LE TRAITEMENT DE LA DEPRESSION
  申请人：NEUROSEARCH AS

  公开号：WO2003042162A1

  公开（公告）日：2003-05-22

  This invention relates to prodrugs of antidepressants and the use of these prodrugs in a method for therapy and to pharmaceutical compositions comprising the prodrugs of the invention.