(E)-N-((R)-1-Hydroxymethyl-propyl)-3-phenyl-N-(2,2,2-trifluoro-ethyl)-acrylamide | 152529-40-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-((R)-1-Hydroxymethyl-propyl)-3-phenyl-N-(2,2,2-trifluoro-ethyl)-acrylamide
• CAS: 152529-40-3
• 化学式: C₁₅H₁₈F₃NO₂
• 分子量: 301.309
• InChiKey: SQGNPLBXILUMBC-MMQHEFTJSA-N

物化性质

• 沸点：
  423.3±45.0 °C(predicted)
• 密度：
  1.214±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-N-((R)-1-Hydroxymethyl-propyl)-3-phenyl-N-(2,2,2-trifluoro-ethyl)-acrylamide 在 硫酸 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 (R) 3-phenylvaleric acid
  参考文献：
  名称：

  Enantioselective Michael additions of Grignard reagents to cinnamamides deriving from N-fluoroalkyl (R)-(−)-2-aminobutan-1-ol. determination of diastereomeric excess by means of 19F NMR

  摘要：

  N-Alkylation of (R)-(-)-2-aminobutan-1-ol 1 (a readily available reagent) with ortho-fluorobenzyl chloride, followed by reaction with cinnamoyl chloride, afforded the cinnamamide (R)-(+)-6. Michael addition of n-alkyl magnesium halides to the latter gave the corresponding adducts (R,R)-8a-e whose diastereomeric excesses were higher than 92% as evidenced by F-19 NMR. Acidic hydrolysis of these adducts yielded the corresponding beta-phenylalkanoic acids (R)-(-)-9a-e.

  DOI：

  10.1016/s0957-4166(00)80345-6
• 作为产物：
  描述：

  2,2,2-Trifluoro-N-((R)-1-hydroxymethyl-propyl)-acetamide 在 lithium aluminium tetrahydride 、 sodium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (E)-N-((R)-1-Hydroxymethyl-propyl)-3-phenyl-N-(2,2,2-trifluoro-ethyl)-acrylamide
  参考文献：
  名称：

  Enantioselective Michael additions of Grignard reagents to cinnamamides deriving from N-fluoroalkyl (R)-(−)-2-aminobutan-1-ol. determination of diastereomeric excess by means of 19F NMR

  摘要：

  N-Alkylation of (R)-(-)-2-aminobutan-1-ol 1 (a readily available reagent) with ortho-fluorobenzyl chloride, followed by reaction with cinnamoyl chloride, afforded the cinnamamide (R)-(+)-6. Michael addition of n-alkyl magnesium halides to the latter gave the corresponding adducts (R,R)-8a-e whose diastereomeric excesses were higher than 92% as evidenced by F-19 NMR. Acidic hydrolysis of these adducts yielded the corresponding beta-phenylalkanoic acids (R)-(-)-9a-e.

  DOI：

  10.1016/s0957-4166(00)80345-6