4-(tert-butoxycarbonyl-difluoro-methyl)-L-phenylalanine | 222842-94-6

• 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: 4-(tert-butoxycarbonyl-difluoro-methyl)-L-phenylalanine
• 英文别名: (2S)-2-amino-3-[4-[1,1-difluoro-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenyl]propanoic acid
• CAS: 222842-94-6
• 化学式: C₁₅H₁₉F₂NO₄
• 分子量: 315.317
• InChiKey: IIFRWZVRHGBUEE-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.62
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 4-(tert-butoxycarbonyl-difluoro-methyl)-L-phenylalanine 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以84%的产率得到N-Fmoc-4-(tert-butoxycarbonyl-difluoro-methyl)-L-phenylalanine
  参考文献：
  名称：

  Synthesis of Fmoc-protected 4-carboxydifluoromethyl-L-phenylalanine: A phosphotyrosyl mimetic of potential use for signal transduction studies

  摘要：

  4-(Carboxymethyl)phenylalanine (2) and its alpha,alpha-difluoro homologue 4-(carboxydifluoromethyl)-phenylalanine (3) have been described as phosphotyrosyl mimetics. Herein we report the synthesis of N-Fmoc 4-(0-tert-butyl carboxymethyl)-phenylalanine (4) and N-Fmoc 4-(0-tert-butyl carboxydifluoromethyl)phenylalanine (5) in high enantiomeric purity. These analogues bear orthogonal protection suitable for the preparation of inhibitors directed against a variety of signal transduction pathways, including SH2 and PTP domains and protein-tyrosine phosphatases. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(99)00076-9
• 作为产物：
  描述：

  benzyl (2R,3S)-3-<4-(tert-butoxycarbonyl-difluoro-methyl)phenyl>-2-oxo-5,6-diphenyl-morpholine-4-carboxylate 在 钯 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 以99%的产率得到4-(tert-butoxycarbonyl-difluoro-methyl)-L-phenylalanine
  参考文献：
  名称：

  Synthesis of Fmoc-protected 4-carboxydifluoromethyl-L-phenylalanine: A phosphotyrosyl mimetic of potential use for signal transduction studies

  摘要：

  4-(Carboxymethyl)phenylalanine (2) and its alpha,alpha-difluoro homologue 4-(carboxydifluoromethyl)-phenylalanine (3) have been described as phosphotyrosyl mimetics. Herein we report the synthesis of N-Fmoc 4-(0-tert-butyl carboxymethyl)-phenylalanine (4) and N-Fmoc 4-(0-tert-butyl carboxydifluoromethyl)phenylalanine (5) in high enantiomeric purity. These analogues bear orthogonal protection suitable for the preparation of inhibitors directed against a variety of signal transduction pathways, including SH2 and PTP domains and protein-tyrosine phosphatases. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(99)00076-9