4-bromo-2,3,5-trimethyl-6-nitrophenol | 1277193-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-bromo-2,3,5-trimethyl-6-nitrophenol
• 英文别名: 4-bromo-3,5,6-trimethyl-2-nitrophenol；4-Bromo-2,3,5-trimethyl-6-nitrophenol
• CAS: 1277193-09-5
• 化学式: C₉H₁₀BrNO₃
• 分子量: 260.087
• InChiKey: MRNIJPUTRMPSLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2,3,5-trimethyl-6-nitrophenol 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 四丁基碘化铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 6-(4-methoxyphenyl)-5,7,8-trimethyl-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  Regulation of the Escherichia coli AtoSC two component system by synthetic biologically active 5;7;8-trimethyl-1;4-benzoxazine analogues

  摘要：

  The Escherichia coli AtoSC two component system; upon acetoacetate induction; regulates the expression of the atoDAEB operon; through His -> Asp phopshotransfer; thus modulating important cellular processes. In this report the effect of seven 5,7,8-trimethyl-1,4-benzoxazine derivatives on the regulation of the E. coli AtoSC system was studied. The new compounds were tested for their effectiveness on the expression of the atoC and the regulated atoDAEB operon. The non-substituted 5,7,8-trimethyl-1,4-benzoxazine (4a), was the most potent inducer on atoC transcription; resulting in accumulation of AtoC protein. The induction of atoC by 4a was specific; since no effect was observed on the other genes of the system (atoS and atoDAEB). Moreover; compound 4a was shown to significantly up-regulate the in vitro kinase activity of the histidine kinase AtoS without altering the protein levels in the cell. Interestingly; this compound appeared to modulate the acetoacetate-mediated induction of the atoDAEB promoter by the AtoSC system. These data provide the first evidence for a differential modulator role of 5,7,8-trimethyl-1,4-benzoxazine; on the AtoSC two component system mediated signaling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.029
• 作为产物：
  描述：

  2-硝基-3,5,6-三甲基苯酚 在 氢溴酸 、 双氧水 、 溶剂黄146 作用下， 以 Petroleum ether 为溶剂， 反应 1.5h， 以68%的产率得到4-bromo-2,3,5-trimethyl-6-nitrophenol
  参考文献：
  名称：

  含氧芳香族化合物卤化的简单有效方法

  摘要：

  提出了一种在石油醚中使用 HX/H 2 O 2 /AcOH 的组合对含氧芳烃进行氯化和溴化的有效和温和的方法，具有良好的区域选择性和优异的收率。研究了超声波的影响。

  DOI：

  10.1055/s-0030-1260792

文献信息

• Divergent synthesis of 2,6-diaryl-substituted 5,7,8-trimethyl-1,4-benzoxazines via microwave-promoted palladium-catalyzed Suzuki–Miyaura cross coupling and biological evaluation
  作者：Eftychia N. Koini、Nicolaos Avlonitis、Erica S. Martins-Duarte、Wanderley de Souza、Rossiane C. Vommaro、Theodora Calogeropoulou

  DOI：10.1016/j.tet.2012.10.009

  日期：2012.12

  An efficient palladium-catalyzed Suzuki-Miyaura cross-coupling protocol effected in a mixture of DME/water (2:1) enables the reaction of sterically hindered and electron rich 6-chloro or 6-bromo-1,4-benzoxazines(ones) with a variety of aryl, vinyl or alkylboronic acids. Coupling is effected with catalyst loading of 5 mol % using sealed-vessel microwave processing. The resulting compounds exhibit potent activity against Toxoplasma gondii tachyzoite proliferation. (C) 2012 Elsevier Ltd. All rights reserved.