ethyl Z-5,5,5-trifluoro-4-methylpent-2-enoate | 371778-11-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl Z-5,5,5-trifluoro-4-methylpent-2-enoate
• CAS: 371778-11-9
• 化学式: C₈H₁₁F₃O₂
• 分子量: 196.169
• InChiKey: XNZXYIWWLAHXLW-PLNGDYQASA-N

物化性质

• 沸点：
  155.7±40.0 °C(predicted)
• 密度：
  1.124±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl Z-5,5,5-trifluoro-4-methylpent-2-enoate 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 、 乙酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Effect of Allylic CH_3-nF_n Groups (n = 1−3) on π-Facial Diastereoselection

  摘要：

  [GRAPHICS]Michael addition of various enolates toward gamma -CH3-nFn-alpha,beta -unsaturated ketones (n = 1-3) was proven to smoothly furnish the 1,4-adducts with high si face selectivities which monotonously decreased by reduction in the number of fluorines. Although the Felkin-Anh model correctly anticipates the present stereochemical outcome only with E-acceptors, the hyperconjugative stabilization of transition states by electron donation from the allylic substituents (the Cieplak rule) successfully explains the pi -facial preference of both acceptors at least in a qualitative level.

  DOI：

  10.1021/ol016401g
• 作为产物：
  描述：

  2-(三氟甲基)丙醛 、 二苯氧基磷基乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 生成 ethyl Z-5,5,5-trifluoro-4-methylpent-2-enoate
  参考文献：
  名称：

  Effect of Allylic CH_3-nF_n Groups (n = 1−3) on π-Facial Diastereoselection

  摘要：

  [GRAPHICS]Michael addition of various enolates toward gamma -CH3-nFn-alpha,beta -unsaturated ketones (n = 1-3) was proven to smoothly furnish the 1,4-adducts with high si face selectivities which monotonously decreased by reduction in the number of fluorines. Although the Felkin-Anh model correctly anticipates the present stereochemical outcome only with E-acceptors, the hyperconjugative stabilization of transition states by electron donation from the allylic substituents (the Cieplak rule) successfully explains the pi -facial preference of both acceptors at least in a qualitative level.

  DOI：

  10.1021/ol016401g