rac-2,3-dihydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide | 908120-11-6

• 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: rac-2,3-dihydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
• 英文别名: rac-O-dephenylandarine；F9JR5Rrp7H；2,3-dihydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• CAS: 908120-11-6
• 化学式: C₁₁H₁₁F₃N₂O₅
• 分子量: 308.214
• InChiKey: FEZWNOHXAIWDTD-UHFFFAOYSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  526.1±50.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-氨基-2-硝基三氟甲苯 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.25h， 生成 rac-2,3-dihydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
  参考文献：
  名称：

  Novel pathway for the synthesis of arylpropionamide-derived selective androgen receptor modulator (SARM) metabolites of andarine and ostarine

  摘要：

  O-Dephenylandarine and O-dephenylostarine, two SARM metabolites relevant for doping control analysis, were synthesized in their endogenous (S)-forms as well as in terms of their racemates. The enantiopure (S)-metabolites were obtained after six steps in 20% and 23% overall yield, the slightly modified racemic route provided the compounds in 28% and 31% total yield, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.065

文献信息

• Novel pathway for the synthesis of arylpropionamide-derived selective androgen receptor modulator (SARM) metabolites of andarine and ostarine
  作者：Katharina M. Schragl、Guro Forsdahl、Guenter Gmeiner、Valentin S. Enev、Peter Gaertner

  DOI：10.1016/j.tetlet.2013.02.065

  日期：2013.5

  O-Dephenylandarine and O-dephenylostarine, two SARM metabolites relevant for doping control analysis, were synthesized in their endogenous (S)-forms as well as in terms of their racemates. The enantiopure (S)-metabolites were obtained after six steps in 20% and 23% overall yield, the slightly modified racemic route provided the compounds in 28% and 31% total yield, respectively. (C) 2013 Elsevier Ltd. All rights reserved.