(S)-2-(3'-nitrobiphenyl-2-yloxy)propionic acid methyl ester | 945619-02-3

• 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: (S)-2-(3'-nitrobiphenyl-2-yloxy)propionic acid methyl ester
• 英文别名: methyl (2S)-2-[2-(3-nitrophenyl)phenoxy]propanoate
• CAS: 945619-02-3
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: VVLZSNUXSOCVHQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(3'-nitrobiphenyl-2-yloxy)propionic acid methyl ester 在 三甲基铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (S)-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：

  D-(+)-乳酸甲酯 、 2-(3-硝基苯基)苯酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(S)-2-(3'-nitrobiphenyl-2-yloxy)propionic acid methyl ester
  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