(Z)-7,7,7-trifluoro-2,2,6-trimethylhept-4-en-3-one | 371778-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-7,7,7-trifluoro-2,2,6-trimethylhept-4-en-3-one
• CAS: 371778-06-2
• 化学式: C₁₀H₁₅F₃O
• 分子量: 208.224
• InChiKey: WITWEEGBQUIAMH-WAYWQWQTSA-N

物化性质

• 沸点：
  62 °C(Press: 14 mmHg)
• 密度：
  1.035±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-7,7,7-trifluoro-2,2,6-trimethylhept-4-en-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：

  ethyl Z-5,5,5-trifluoro-4-methylpent-2-enoate 在 sodium hydroxide 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 (Z)-7,7,7-trifluoro-2,2,6-trimethylhept-4-en-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

文献信息

• Effect of Allylic CH₃_-<i>_n</i>F<i>_n</i> Groups (<i>n</i> = 1−3) on π-Facial Diastereoselection
  作者：Takashi Yamazaki、Tatsuro Ichige、Satoshi Takei、Seiji Kawashita、Tomoya Kitazume、Toshio Kubota

  DOI：10.1021/ol016401g

  日期：2001.9.1

  [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.