N-Phthaloyl-β-bromo-β-alanine methyl ester | 135395-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-Phthaloyl-β-bromo-β-alanine methyl ester
• 英文别名: Methyl 3-bromo-3-(1,3-dioxoisoindol-2-yl)propanoate
• CAS: 135395-26-5
• 化学式: C₁₂H₁₀BrNO₄
• 分子量: 312.12
• InChiKey: HIVKUOYQIGSKTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Phthaloyl-β-bromo-β-alanine methyl ester 在 过氧化双月桂酰 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 0.42h， 生成
  参考文献：
  名称：

  A convergent route to functional protected amines, diamines, and β-amino acids

  摘要：

  Phthalimide protected amines react with NBS under peroxide initiation to give geminal phthalimidobromo derivatives, which are readily converted into the corresponding xanthates. These xanthates in turn undergo radical additions to numerous olefins, providing a convergent and modular access to densely functionalized protected amines and diamines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.055
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 7.0h， 生成 N-Phthaloyl-β-bromo-β-alanine methyl ester
  参考文献：
  名称：

  A convergent route to functional protected amines, diamines, and β-amino acids

  摘要：

  Phthalimide protected amines react with NBS under peroxide initiation to give geminal phthalimidobromo derivatives, which are readily converted into the corresponding xanthates. These xanthates in turn undergo radical additions to numerous olefins, providing a convergent and modular access to densely functionalized protected amines and diamines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.055

文献信息

• 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.