2-溴-2-硝基-1-(4-甲氧基苯基)丙酮 | 1092094-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-2-硝基-1-(4-甲氧基苯基)丙酮
• 英文名称: 2-bromo-2-nitro-1-(4-methoxyphenyl)propanone
• 英文别名: 2-Bromo-1-(4-methoxyphenyl)-2-nitropropan-1-one
• CAS: 1092094-17-1
• 化学式: C₁₀H₁₀BrNO₄
• 分子量: 288.098
• InChiKey: VKINSSCIDUZOIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-nitro-1-hydroxy-1-(4-methoxy-phenyl)-propane 在 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl 、 碳酸氢钠 、 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 、 水 为溶剂， 以87%的产率得到4'-methoxy-2-nitropropiophenone
  参考文献：
  名称：

  A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine–bromine complexes

  摘要：

  A new TEMPO-mediated catalytic oxidation method in combination with Py center dot HBr3 (stoichiometric) is developed for oxidation of secondary alcohols to the corresponding ketones. The performance of this oxidizing system is better compared with that of TEMPO method combined with R4NBr3 center dot Poly(4-vinylpyridine) HBr3 can be used in place of Py center dot HBr3. The electron-withdrawing substituent at the C-4 position of TEMPO increases the reactivity of TEMPO significantly in the oxidation of electron-deficient alcohols Such as polyhaloalkylmethanols. Inductive effect of the substituent of TEMPO is discussed through the characterization of the redox potential of N-O radical by cyclic voltammetry. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.051