(2R,3S)-2-Amino-3-(4-methoxy-phenyl)-butyric acid | 754977-47-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,3S)-2-Amino-3-(4-methoxy-phenyl)-butyric acid
• 英文别名: (2R,3S)-2-amino-3-(4-methoxyphenyl)butanoic acid
• CAS: 754977-47-4
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: HYOLSKLZTOUWNN-OIBJUYFYSA-N

物化性质

• 沸点：
  354.0±37.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-Amino-3-(4-methoxy-phenyl)-butyric acid 在 盐酸 、 氢溴酸 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 生成 (2R,3S,2'S)-N,O-Bis<2-(trifluoromethyl)-2-methoxyphenylacetyl>-β-methyltyrosine isobutyl ester
  参考文献：
  名称：

  Efficient method for the total asymmetric synthesis of the isomers of .beta.-methyltyrosine

  摘要：

  Alpha-Amino acids modified at the beta-carbon atom can provide topographical constraints when incorporated into a peptide. Such modifications can modulate the physical, chemical, and biological properties of the compound. In order to properly evaluate the effect of such modifications, large-scale asymmetric syntheses of the isomers are needed. A method for the stereoselective large-scale synthesis of an four stereoisomers of beta-methyltyrosine is described in this paper. The stereochemistry of both the alpha- and beta-stereocenters was set using 4-phenyl-2-oxazolidinone as a chiral auxiliary. The key reactions were an asymmetric Michael-like addition of an organocuprate to a chiral alpha,beta-unsaturated acyloxazolidinone (beta center) and subsequent stereoselective electrophilic bromination of the resulting product (alpha center). Conversion of the bromide to the azide, catalyzed hydrolysis to the azido acid with simultaneous recovery of the chiral auxiliary, reduction of the azide, and final deprotection of the phenol group afforded the desired amino acids. In general, the reactions were performed in yields over 80 %, and the isomers were obtained in enantiomeric purities of 98:2 to 99:1.

  DOI：

  10.1021/jo00078a042
• 作为产物：
  描述：

  [(3R)-3-(4-methoxyphenyl)butanoyl] 2,2-dimethylpropanoate 在 palladium on activated charcoal lithium hydroxide 、 双氧水 、 ammonium formate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.5h， 生成 (2R,3S)-2-Amino-3-(4-methoxy-phenyl)-butyric acid
  参考文献：
  名称：

  异常氨基酸的不对称合成：β-甲基酪氨酸的旋光异构体的合成

  摘要：

  β-甲基酪氨酸的光学纯异构体的合成已经完成。

  DOI：

  10.1016/s0040-4039(01)93367-2