2-(N-bromo-N-phenylamino)-2-(4-chlorophenyl) acetic acid | 1570162-31-0

• 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: 2-(N-bromo-N-phenylamino)-2-(4-chlorophenyl) acetic acid
• 英文别名: 2-(N-bromoanilino)-2-(4-chlorophenyl)acetic acid
• CAS: 1570162-31-0
• 化学式: C₁₄H₁₁BrClNO₂
• 分子量: 340.604
• InChiKey: VXQCXZSETDZFFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二氧化碳 、 1-(4-氯苯基)-N-苯基甲亚胺 在 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、4.0 MPa 条件下， 以52%的产率得到2-(N-bromo-N-phenylamino)-2-(4-chlorophenyl) acetic acid
  参考文献：
  名称：

  Electrogenerated-bases promoted electrochemical synthesis of N-bromoamino acids from imines and carbon dioxide

  摘要：

  In this paper, the one-step synthesis of N-bromoamino acids has been developed by electrolyzing imines and carbon dioxide (4 MPa). The electrosynthesis was performed in an undivided cell with Ni cathode and Al sacrificial anode containing n-Bu4NBr-DMF as supporting electrolyte with a constant current at room temperature. The N-bromoamino acids were afforded in moderate to good yields rather than traditional a-amino acids. To explore the truth, some influenced factors (cathode materials, supporting electrolyte, and electricity etc.) were investigated. The experimental results indicated that the NH group of the alpha-amino acid could be deprotonated by alkyl anion R- (carbanion, a strong base), followed by the oxidation of hypobromous acid resulted from the two-step oxidation of the bromide ion at the anode, and produced the N-bromoamino acid. Finally, the reaction mechanism was briefly discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.054

文献信息

• Electrogenerated-bases promoted electrochemical synthesis of N-bromoamino acids from imines and carbon dioxide
  作者：Chuan-Hua Li、Xiang-Zhi Song、Li-Ming Tao、Qiang-Guo Li、Jin-Qi Xie、Meng-Na Peng、Lan Pan、Chao Jiang、Zhi-Yu Peng、Man-Fen Xu

  DOI：10.1016/j.tet.2014.01.054

  日期：2014.3

  In this paper, the one-step synthesis of N-bromoamino acids has been developed by electrolyzing imines and carbon dioxide (4 MPa). The electrosynthesis was performed in an undivided cell with Ni cathode and Al sacrificial anode containing n-Bu4NBr-DMF as supporting electrolyte with a constant current at room temperature. The N-bromoamino acids were afforded in moderate to good yields rather than traditional a-amino acids. To explore the truth, some influenced factors (cathode materials, supporting electrolyte, and electricity etc.) were investigated. The experimental results indicated that the NH group of the alpha-amino acid could be deprotonated by alkyl anion R- (carbanion, a strong base), followed by the oxidation of hypobromous acid resulted from the two-step oxidation of the bromide ion at the anode, and produced the N-bromoamino acid. Finally, the reaction mechanism was briefly discussed. (C) 2014 Elsevier Ltd. All rights reserved.