N-tert-Butyl-N^α-phthaloyl-β-bromophenylalaninamide | 280747-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-tert-Butyl-N^α-phthaloyl-β-bromophenylalaninamide
• 英文别名: 3-bromo-N-tert-butyl-N^α-phthaloylphenylalaninamide；3-bromo-N-tert-butyl-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanamide
• CAS: 280747-80-0
• 化学式: C₂₁H₂₁BrN₂O₃
• 分子量: 429.313
• InChiKey: HGDGQMIKCJDCLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 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：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-Butyl-N^α-phthaloyl-β-bromophenylalaninamide 、 18-冠醚-6 、 乙腈 、 氟化钾，无水 以84%的产率得到
  参考文献：
  名称：

  EASTON, CHRISTOPHER J.;HUTTON, CRAIG A.;ROSELT, PETER D.;TIEKINK, EDWARD +, AUSTRAL. J. CHEM., 44,(1991) N, C. 687-694

  摘要：

  DOI：
• 作为产物：
  描述：

  (RS)-N-(tert-Butyl)-N^α-phthaloylphenylalaninamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 0.25h， 生成 N-tert-Butyl-N^α-phthaloyl-β-bromophenylalaninamide
  参考文献：
  名称：

  Regioselective functionalization of N-phthaloyl-substituted amino acid and peptide derivatives

  摘要：

  The free-radical reactions of a range of amino acid derivatives with N-bromosuccinimide are described. The products and relative rates of these reactions indicate that the alpha-position of an N-phthaloyl-substituted alpha-amino acid derivative is much less reactive than that of a corresponding N-acyl amino acid derivative toward hydrogen atom transfer. This is attributed to the proactive effects of acylamino and carboxyl substituents, in contrast to the counteractive effects of phthalimido and carboxyl groups. The reactions exemplify procedures for the regiocontrolled functionalization of amino acid and peptide derivatives.

  DOI：

  10.1021/jo00019a029

文献信息

• Easton, Christopher J.; Merrett, Martin C.; Razzino, Pasquale, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 4, p. 693 - 697
  作者：Easton, Christopher J.、Merrett, Martin C.、Razzino, Pasquale

  DOI：——

  日期：——
• EASTON, CHRISTOPHER J.;HUTTON, CRAIG A.;ROSELT, PETER D.;TIEKINK, EDWARD +, AUSTRAL. J. CHEM., 44,(1991) N, C. 687-694
  作者：EASTON, CHRISTOPHER J.、HUTTON, CRAIG A.、ROSELT, PETER D.、TIEKINK, EDWARD +

  DOI：——

  日期：——
• Regioselective functionalization of N-phthaloyl-substituted amino acid and peptide derivatives
  作者：Christopher J. Easton、Craig A. Hutton、Giovanna Rositano、Eng Wui Tan

  DOI：10.1021/jo00019a029

  日期：1991.9

  The free-radical reactions of a range of amino acid derivatives with N-bromosuccinimide are described. The products and relative rates of these reactions indicate that the alpha-position of an N-phthaloyl-substituted alpha-amino acid derivative is much less reactive than that of a corresponding N-acyl amino acid derivative toward hydrogen atom transfer. This is attributed to the proactive effects of acylamino and carboxyl substituents, in contrast to the counteractive effects of phthalimido and carboxyl groups. The reactions exemplify procedures for the regiocontrolled functionalization of amino acid and peptide derivatives.