(Z)-ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate | 85571-82-0

• 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: (Z)-ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate
• 英文别名: ethyl (Z)-2,4,4,5,5,5-hexafluoropent-2-enoate
• CAS: 85571-82-0
• 化学式: C₇H₆F₆O₂
• 分子量: 236.114
• InChiKey: WINHFEKAVPCWSC-ARJAWSKDSA-N

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

• 作为反应物：
  描述：

  (Z)-ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate 以72%的产率得到
  参考文献：
  名称：

  KITAZUME, TOMOYA;ISHIKAWA, NOBUO, CHEM. LETT., 1983, N 2, 237-238

  摘要：

  DOI：
• 作为产物：
  描述：

  五氟丙酸乙酯 、 ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate lithium salt 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 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：

  Preparation of α-fluoro-α,β-unsaturated esters two carbon homologation of esters

  摘要：

  DOI：

  10.1016/s0040-4039(01)93802-x

文献信息

• ASYMMETRICAL REDUCTION OF PERFLUOROALKYLATED KETONES, KETOESTERS AND VINYL COMPOUNDS WITH BAKER’S YEAST
  作者：Tomoya Kitazume、Nobuo Ishikawa

  DOI：10.1246/cl.1983.237

  日期：1983.2.5

  Reduction of perfluoroalkylated ketones, ketoesters and vinyl compounds with baker’s yeast was studied. The ketones and β-ketoesters were asymmetrically reduced to give optically active perfluoroalkylated carbinols and hydroxyesters, while the vinyl compounds were reduced to perfluoroalkylated alkanes.

  研究了用面包酵母还原全氟烷基化酮、酮酯和乙烯基化合物。酮和 β-酮酯被不对称地还原成光学活性的全氟烷基化甲醇和羟基酯，而乙烯基化合物被还原成全氟烷基化烷烃。
• 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.
• THENAPPAN, ALAGAPPAN;BURTON, DONALD J., TETRAHEDRON LETT., 30,(1989) N1, C. 5571-5574
  作者：THENAPPAN, ALAGAPPAN、BURTON, DONALD J.

  DOI：——

  日期：——
• THENAPPAN, ALAGAPPAN;BURTON, DONALD J., J. ORG. CHEM., 55,(1990) N5, C. 4639-4642
  作者：THENAPPAN, ALAGAPPAN、BURTON, DONALD J.

  DOI：——

  日期：——