N-(2-bromoallyl)-N-(4-nitrophenyl)acetamide | 1448025-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-bromoallyl)-N-(4-nitrophenyl)acetamide
• 英文别名: N-(2-bromoprop-2-enyl)-N-(4-nitrophenyl)acetamide
• CAS: 1448025-41-9
• 化学式: C₁₁H₁₁BrN₂O₃
• 分子量: 299.124
• InChiKey: CNOAGFOYHIOGSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-bromoallyl)-N-(4-nitrophenyl)acetamide 在 calcium hypobromite 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以96%的产率得到N-(3-bromo-2-oxopropyl)-N-(4-nitrophenyl)acetamide
  参考文献：
  名称：

  Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones

  摘要：

  Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting alpha-arylamino-alpha'-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)(2)] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.118
• 作为产物：
  描述：

  4-硝基苯胺 在 calcium oxide 作用下， 以 2-甲基四氢呋喃 、 乙腈 为溶剂， 反应 3.08h， 生成 N-(2-bromoallyl)-N-(4-nitrophenyl)acetamide
  参考文献：
  名称：

  Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones

  摘要：

  Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting alpha-arylamino-alpha'-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)(2)] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.118

文献信息

• Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones
  作者：Vittorio Pace、Laura Castoldi、María J. Hernáiz、Andrés R. Alcántara、Wolfgang Holzer

  DOI：10.1016/j.tetlet.2013.05.118

  日期：2013.8

  Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting alpha-arylamino-alpha'-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)(2)] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation. (c) 2013 Elsevier Ltd. All rights reserved.