tert-butyl (2-bromoallyl)(p-tolyl)carbamate | 1448025-46-4

• 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: tert-butyl (2-bromoallyl)(p-tolyl)carbamate
• CAS: 1448025-46-4
• 化学式: C₁₅H₂₀BrNO₂
• 分子量: 326.233
• InChiKey: ZUENTOFGLYEIOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-bromoallyl)(p-tolyl)carbamate 在 calcium hypobromite 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以86%的产率得到tert-butyl (3-bromo-2-oxopropyl)(p-tolyl)carbamate
  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：

  乙烷,三氯氟- 在 calcium oxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 3.08h， 生成 tert-butyl (2-bromoallyl)(p-tolyl)carbamate
  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