D-2-氟苯丙氨酸 | 122839-51-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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
• 中文名称: D-2-氟苯丙氨酸
• 中文别名: 2-氟-D-苯丙氨酸
• 英文名称: 2-fluoro-D-phenylalanine ; hydrochloride
• 英文别名: 2-Fluor-D-phenylalanin; Hydrochlorid；H-D-Phe(2-F)-OH.HCl；(2R)-2-amino-3-(2-fluorophenyl)propanoic acid;hydrochloride
• CAS: 122839-51-4
• 化学式: C₉H₁₀FNO₂*ClH
• 分子量: 219.643
• InChiKey: YSTOPARNEYKWBQ-DDWIOCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  (Z)-2-Benzoylamino-3-(2-fluoro-phenyl)-acrylic acid 在 盐酸 、 cationic rhodium complex with (+)-(S)-"Propraphos" 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 8.0h， 生成 D-2-氟苯丙氨酸
  参考文献：
  名称：

  Unusual amino acids

  摘要：

  Few (Z)-alpha-N-benzoylamino-beta-(fluorophenyl)-acrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-(fluorophenyl)-alanine derivatives with optical yields up to 90% using the rhodium complexes of "PROPRAPHOS" and O,N-bis(diphenylphosphino)-2-exo-hydroxy, 3-endo-methylamino-norbornane as chiral catalysts. The method proved to be apt for upscaling the preparation. Deacylation of the obtained amino acids gave the hydrochlorides of the fluorinated phenylalanines in very pure state.

  DOI：

  10.1016/s0957-4166(00)80262-1

文献信息

• Unusual amino acids
  作者：Hans-Walter Krause、Hans-Jörn Kreuzfeld、Christian Döbler

  DOI：10.1016/s0957-4166(00)80262-1

  日期：1992.4

  Few (Z)-alpha-N-benzoylamino-beta-(fluorophenyl)-acrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-(fluorophenyl)-alanine derivatives with optical yields up to 90% using the rhodium complexes of "PROPRAPHOS" and O,N-bis(diphenylphosphino)-2-exo-hydroxy, 3-endo-methylamino-norbornane as chiral catalysts. The method proved to be apt for upscaling the preparation. Deacylation of the obtained amino acids gave the hydrochlorides of the fluorinated phenylalanines in very pure state.