2-[{(1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino}methyl]-4-bromophenol | 52372-28-8

• 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: 2-[{(1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino}methyl]-4-bromophenol
• 英文别名: 4-bromo-2-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]iminomethyl]phenol
• CAS: 52372-28-8
• 化学式: C₁₆H₁₆BrNO₂
• 分子量: 334.213
• InChiKey: MGRFUKFJVLOAPZ-BDJLRTHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  左旋去甲麻黄碱 、 5-溴水杨醛 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到2-[{(1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino}methyl]-4-bromophenol
  参考文献：
  名称：

  八个席夫碱的X射线晶体学和光谱性质，作为质子转移反应的证据。分子间氢键的作用†

  摘要：

  进行了几种邻羟基席夫碱的光谱研究，并分析了相应的晶体结构，以确定其特征性的氢键模式。X射线分析表明，烯醇（O–H⋯N）互变异构体在化合物1-3中最稳定，而酮基（N–H⋯O）形式在化合物4–7中更可取。讨论了控制每个互变异构体超分子排列的特定分子间O–H⋯O氢键相互作用。此外，使用固态NMR和IR实验可以对多晶样品进行完整的表征。还使用溶液VT NMR和紫外可见光实验获得有关互变异构体性质和稳定性的宝贵见解。

  DOI：

  10.1039/c0nj00179a

文献信息

• Antibacterial Activities of 4-Substituted-2-[(E)-{(1S,2R)/(1R,2S)-1-Hydroxy-1-Phenylpropan-2-Ylimino}Methyl]Phenol
  作者：Manoharan Muthu Tamizh、Devarayan Kesavan、Ponnurengam Malliappan Sivakumar、Kurt Mereiter、Mohan Deepa、Karl Kirchner、Mukesh Doble、Ramasamy Karvembu

  DOI：10.1111/j.1747-0285.2011.01263.x

  日期：2012.2

  A series of norephedrine‐based Schiff bases (1a–6a and 1b–6b) were synthesized by reacting substituted salicylaldehydes with d‐norephedrine or l‐norephedrine. The structure of these compounds was confirmed by elemental analyses and spectroscopic techniques. The molecular structures of 5a and 6a have been determined by X‐ray crystallography, which revealed that the compounds are in the oxoamino form, with bent intramolecular N‐H···O (N···O ≈ 2.58 Å) hydrogen bonds and that they are associated in dimers bridged by linear intermolecular O‐H···O (O···O ≈ 2.69 Å) hydrogen bonds. The density functional theory calculations on 5a confirmed that the oxoamino form is more stable than the phenolimino form by 12.2 kcal/mol. All the compounds were evaluated for their antibacterial activity using resazurin dye as indicator by twofold dilution method against four bacteria namely, Bacillus subtilis (NCIM2718), Staphylococcus aureus (NCIM5021), Escherichia coli (NCIM2931), and Proteus vulgaris (NCIM2813).