(2S,3R)-3-hydroxy-N-tert-butyl-N^α-phthaloyl-3-(4-fluoro-3-nitrophenyl)alaninamide | 230313-46-9

• 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: (2S,3R)-3-hydroxy-N-tert-butyl-N^α-phthaloyl-3-(4-fluoro-3-nitrophenyl)alaninamide
• 英文别名: (2S,3R)-N-tert-butyl-2-(1,3-dioxoisoindol-2-yl)-3-(4-fluoro-3-nitrophenyl)-3-hydroxypropanamide
• CAS: 230313-46-9
• 化学式: C₂₁H₂₀FN₃O₆
• 分子量: 429.405
• InChiKey: FRMLSFDXUGRBCY-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-hydroxy-N-tert-butyl-N^α-phthaloyl-3-(4-fluoro-3-nitrophenyl)alaninamide 在 盐酸 、 溶剂黄146 作用下， 反应 5.0h， 以82%的产率得到(2S,3R)-3-hydroxy-3-(4-fluoro-3-nitrophenyl)alanine
  参考文献：
  名称：

  Synthesis of β-Hydroxy-β-(fluoronitrophenyl)alanines:  Vital Components in the Assembly of Biologically Active Cyclic Peptides

  摘要：

  [GRAPHICS]Numerous biologically active cyclic peptides, such as the antibiotic vancomycin, contain amino acid residues connected through side-chain biaryl or aryl-alkyl ether linkages. Nucleophilic aromatic substitution reactions have recently been shown to provide a general method for the formation of such ether linkages, and consequently the synthesis of functionalized fluoronitro-substituted aromatic amino acids is of great interest. Herein, a method for the stereospecific synthesis of 3-fluoro-4-nitro- and 4-fluoro-3-nitro-threo-beta-hydroxyphenylalanine described.

  DOI：

  10.1021/ol9906054
• 作为产物：
  描述：

  N-乙氧羰基邻苯二甲酰亚胺 在 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 、 silver sulfate 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 77.92h， 生成 (2S,3R)-3-hydroxy-N-tert-butyl-N^α-phthaloyl-3-(4-fluoro-3-nitrophenyl)alaninamide
  参考文献：
  名称：

  Synthesis of β-Hydroxy-β-(fluoronitrophenyl)alanines:  Vital Components in the Assembly of Biologically Active Cyclic Peptides

  摘要：

  [GRAPHICS]Numerous biologically active cyclic peptides, such as the antibiotic vancomycin, contain amino acid residues connected through side-chain biaryl or aryl-alkyl ether linkages. Nucleophilic aromatic substitution reactions have recently been shown to provide a general method for the formation of such ether linkages, and consequently the synthesis of functionalized fluoronitro-substituted aromatic amino acids is of great interest. Herein, a method for the stereospecific synthesis of 3-fluoro-4-nitro- and 4-fluoro-3-nitro-threo-beta-hydroxyphenylalanine described.

  DOI：

  10.1021/ol9906054

文献信息

• Synthesis of β-Hydroxy-β-(fluoronitrophenyl)alanines:  Vital Components in the Assembly of Biologically Active Cyclic Peptides
  作者：Craig A. Hutton

  DOI：10.1021/ol9906054

  日期：1999.7.1

  [GRAPHICS]Numerous biologically active cyclic peptides, such as the antibiotic vancomycin, contain amino acid residues connected through side-chain biaryl or aryl-alkyl ether linkages. Nucleophilic aromatic substitution reactions have recently been shown to provide a general method for the formation of such ether linkages, and consequently the synthesis of functionalized fluoronitro-substituted aromatic amino acids is of great interest. Herein, a method for the stereospecific synthesis of 3-fluoro-4-nitro- and 4-fluoro-3-nitro-threo-beta-hydroxyphenylalanine described.