(R)-2-(3'-nitrobiphenyl-2-yloxy)propionitrile | 945619-07-8

• 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: (R)-2-(3'-nitrobiphenyl-2-yloxy)propionitrile
• 英文别名: (2R)-2-[2-(3-nitrophenyl)phenoxy]propanenitrile
• CAS: 945619-07-8
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: VJDKISULZPYFNF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(3'-nitrobiphenyl-2-yloxy)propionitrile 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 16.0h， 生成 (R)-2-[1-(3'-nitrobiphenyl-2-yloxy)ethyl]-4,5-dihydroimidazole-1-carboxylic acid [(R)-1-phenylethyl]amide
  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：

  (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