(S)-4-(2-Amino-phenyl)-2-hydroxy-butyric acid methyl ester | 192204-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-(2-Amino-phenyl)-2-hydroxy-butyric acid methyl ester
• 英文别名: methyl (2S)-4-(2-aminophenyl)-2-hydroxybutanoate
• CAS: 192204-22-1
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: OBNCSSYBNUWRIK-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 (S)-4-(2-Amino-phenyl)-2-hydroxy-butyric acid methyl ester 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以84%的产率得到(S)-4-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl]-2-hydroxy-butyric acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of a Thymine Derivative of (S)-2-Hydroxy-4-(2-aminophenyl)butanoic Acid. A Novel Building Block for the Synthesis of Aromatic Peptidic Nucleic Acid Oligomers¹

  摘要：

  The synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical peptide synthesis. UV absorption spectra and H-1 NMR data of this tetramer suggested that base stacking interactions in the APNA oligomers may be favorable.

  DOI：

  10.1021/jo962326p
• 作为产物：
  描述：

  Sodium; (E)-4-(2-nitro-phenyl)-2-oxo-but-3-enoate 在 palladium on activated charcoal 盐酸 、 1,4-dihydronicotinamide adenine dinucleotide 、 氢气 、 sodium formate 、 三羟甲基氨基甲烷盐酸盐 、 1,4-二巯基-2,3-丁二醇 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 39.0h， 生成 (S)-4-(2-Amino-phenyl)-2-hydroxy-butyric acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of a Thymine Derivative of (S)-2-Hydroxy-4-(2-aminophenyl)butanoic Acid. A Novel Building Block for the Synthesis of Aromatic Peptidic Nucleic Acid Oligomers¹

  摘要：

  The synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical peptide synthesis. UV absorption spectra and H-1 NMR data of this tetramer suggested that base stacking interactions in the APNA oligomers may be favorable.

  DOI：

  10.1021/jo962326p