(2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide | 897364-32-8

• 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: (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide
• 英文别名: (2S)-2-[tert-butyl(dimethyl)silyl]oxy-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenoxy)-2-methylpropanamide
• CAS: 897364-32-8
• 化学式: C₂₄H₂₈F₄N₂O₃Si
• 分子量: 496.577
• InChiKey: CUKUIOOCOAAADX-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide 、 碘甲烷 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以37%的产率得到(2S)-2-(4-cyano-3-trifluoromethylphenoxy)-3-(4-fluorophenoxy)-2,N-dimethlpropionamide
  参考文献：
  名称：

  Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N→O shift of disubstituted phenyl ring of a bicalutamide derivative

  摘要：

  A novel 1,4-N -> O migration of a disubstituted phenyl ring was observed during N-methylation of a bicalutamide derivative, (2S)-2-(tert-butyidimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide, in the presence of CsF-Celite/acetonitrite and desilylation of (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2,N-dimethylpropionamide in tetra-n-butylammonium fluoride/THF. Both NMR and X-ray analysis confirmed the structure of the 1,4-N -> O disubstituted phenyl ring migrated product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.154
• 作为产物：
  描述：

  (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 、 丁酮 为溶剂， 反应 2.0h， 生成 (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide
  参考文献：
  名称：

  Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N→O shift of disubstituted phenyl ring of a bicalutamide derivative

  摘要：

  A novel 1,4-N -> O migration of a disubstituted phenyl ring was observed during N-methylation of a bicalutamide derivative, (2S)-2-(tert-butyidimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide, in the presence of CsF-Celite/acetonitrite and desilylation of (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2,N-dimethylpropionamide in tetra-n-butylammonium fluoride/THF. Both NMR and X-ray analysis confirmed the structure of the 1,4-N -> O disubstituted phenyl ring migrated product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.154