(E)-ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate | 126275-24-9

• 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: (E)-ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate
• 英文别名: ethyl (E)-2,4,4,5,5,5-hexafluoropent-2-enoate
• CAS: 126275-24-9
• 化学式: C₇H₆F₆O₂
• 分子量: 236.114
• InChiKey: WINHFEKAVPCWSC-ONEGZZNKSA-N

物化性质

• 沸点：
  156.8±40.0 °C(predicted)
• 密度：
  1.358±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  diisopropyl(fluorocarbethoxymethyl)phosphonate 、 (Z)-1-fluoro-1-phenyl-2-pentafluoroethyl ethene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E)-ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate 、 (Z)-ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate
  参考文献：
  名称：

  SYNTHESIS OF PHENYL AND ESTER SUBSTITUTED VINYL FLUORIDES VIA REDUCTION AND OLEFINATION OF ESTERS

  摘要：

  A reduction-olefination sequence has been used to convert ethyl pentafluoropropanoate 6 to 1-fluoro-1-phenyl-2-pentafluoroethyl ethene 7 and ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate 8. Addition of lithium diethyl alpha -fluorobenzylphosphonate [(EtO)(2)P(O)CFPh](-) Li+ 4 or lithium fluorocarboethoxymethylene dialkylphosphonate [(RO)(2)P(O)CFCO2Et](-) Li+ 5 (R = Et, i-Pr) to a THF solution of fluorinated aldehydes prepared in situ from 6 and diisobutylaluminum hydride (DIBAL) affords the vinyl fluorides C2F5CH=CFPh 7 and C2F5CH=CFCO2Et 8 in good yields. However, yields of the final products 7 and 8 are low when in situ reduction of 6 to aldehyde was performed in the presence of lithium salts of 4 or 5.

  DOI：

  10.1080/10426509808035739

文献信息

• Preparation of α-fluoro-α,β-unsaturated esters two carbon homologation of esters
  作者：Alagappan Thenappan、Donald J. Burton

  DOI：10.1016/s0040-4039(01)93802-x

  日期：1989.1
• Reduction-olefination of esters: a new and efficient synthesis of .alpha.-fluoro .alpha.,.beta.-unsaturated esters
  作者：Alagappan Thenappan、Donald J. Burton

  DOI：10.1021/jo00302a030

  日期：1990.7
• SYNTHESIS OF PHENYL AND ESTER SUBSTITUTED VINYL FLUORIDES VIA REDUCTION AND OLEFINATION OF ESTERS
  作者：Hou-jen Tsai、Donald J. Burton

  DOI：10.1080/10426509808035739

  日期：1998.9.1

  A reduction-olefination sequence has been used to convert ethyl pentafluoropropanoate 6 to 1-fluoro-1-phenyl-2-pentafluoroethyl ethene 7 and ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate 8. Addition of lithium diethyl alpha -fluorobenzylphosphonate [(EtO)(2)P(O)CFPh](-) Li+ 4 or lithium fluorocarboethoxymethylene dialkylphosphonate [(RO)(2)P(O)CFCO2Et](-) Li+ 5 (R = Et, i-Pr) to a THF solution of fluorinated aldehydes prepared in situ from 6 and diisobutylaluminum hydride (DIBAL) affords the vinyl fluorides C2F5CH=CFPh 7 and C2F5CH=CFCO2Et 8 in good yields. However, yields of the final products 7 and 8 are low when in situ reduction of 6 to aldehyde was performed in the presence of lithium salts of 4 or 5.