(R)-2-(3'-nitrobiphenyl-2-yloxy)propionamide | 945619-05-6

• 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: (R)-2-(3'-nitrobiphenyl-2-yloxy)propionamide
• 英文别名: (2R)-2-[2-(3-nitrophenyl)phenoxy]propanamide
• CAS: 945619-05-6
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: VHLOUWMRVIELCC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(3'-nitrobiphenyl-2-yloxy)propionamide 在 吡啶 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以70%的产率得到(R)-2-(3'-nitrobiphenyl-2-yloxy)propionitrile
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation. 3. (R)-(+)-m-Nitrobiphenyline, a New Efficient and α_2C-Subtype Selective Agonist

  摘要：

  To assess the stereochemical requirements for efficient (alpha(2C)-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(+/-)-5] were prepared and tested on cells expressing the human alpha(2)-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(-)-5 in producing (alpha(2C)-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(+/-)-l] whose (S)-(-)-form proved the preferred (alpha(2C)-configuration.

  DOI：

  10.1021/jm061487a
• 作为产物：
  描述：

  2-(3-硝基苯基)苯酚 、 (S)-2-[(p-tolylsulfonyl)oxy]propionamide 在 potassium methanolate 作用下， 以 丁酮 为溶剂， 反应 25.0h， 以70%的产率得到(R)-2-(3'-nitrobiphenyl-2-yloxy)propionamide
  参考文献：
  名称：

  α₂-Adrenoreceptors Profile Modulation. 3. (R)-(+)-m-Nitrobiphenyline, a New Efficient and α_2C-Subtype Selective Agonist

  摘要：

  To assess the stereochemical requirements for efficient (alpha(2C)-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(+/-)-5] were prepared and tested on cells expressing the human alpha(2)-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(-)-5 in producing (alpha(2C)-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(+/-)-l] whose (S)-(-)-form proved the preferred (alpha(2C)-configuration.

  DOI：

  10.1021/jm061487a