(E)-7-fluoro-2,2,6-trimethylhept-4-ene-3-one | 371778-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-7-fluoro-2,2,6-trimethylhept-4-ene-3-one
• CAS: 371778-04-0
• 化学式: C₁₀H₁₇FO
• 分子量: 172.243
• InChiKey: WIFZCKXSMTUSCS-GJIOHYHPSA-N

物化性质

• 沸点：
  221.5±25.0 °C(predicted)
• 密度：
  0.905±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-7-fluoro-2,2,6-trimethylhept-4-ene-3-one 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 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：

  (3,3-二甲基-2-氧代丁基)膦酸二乙酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 6.5h， 生成 (E)-7-fluoro-2,2,6-trimethylhept-4-ene-3-one
  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