2,4,4,5,5,6,6,6-Octafluoro-3-oxo-hexanoic acid ethyl ester | 127224-03-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2,4,4,5,5,6,6,6-Octafluoro-3-oxo-hexanoic acid ethyl ester
• 英文别名: Ethyl 2,4,4,5,5,6,6,6-octafluoro-3-oxohexanoate
• CAS: 127224-03-7
• 化学式: C₈H₆F₈O₃
• 分子量: 302.121
• InChiKey: KLDDBDKKWQIXLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(Diethoxy-phosphoryl)-2,4,4,5,5,6,6,6-octafluoro-3-oxo-hexanoic acid ethyl ester 在 碳酸氢钠 作用下， 反应 6.0h， 生成 2,4,4,5,5,6,6,6-Octafluoro-3-oxo-hexanoic acid ethyl ester
  参考文献：
  名称：

  Acylation of fluorocarbethoxy-substituted ylides: a simple and general route to .alpha.-fluoro .beta.-keto esters

  摘要：

  (Fluorocarbethoxymethylene)tri-n-butylphosphorane (3) reacts with acid chlorides and anhydrides to form the corresponding carbon acylated phosphonium salts 4, and hydrolysis of 4 under mild basic conditions provides RCOCFHCOOEt (8) in moderate yields. The reaction is applicable to primary, secondary, tertiary, cyclic, aromatic, and ester-substituted acid chlorides. Acylation with ethyl chloroformate and ethyl chlorothioformate leads to the diesters CFH(COOEt)2 and EtSCOCFHCOOEt. Extension of this reaction sequence to perfluorinated and partially fluorinated acid chlorides did not proceed cleanly to give the expected phosphonium salts. However, the anion derived from (EtO)2P(O)CFHC(O)OEt reacts with R(F)COCl to form the corresponding C-acylated phosphonates 10, and hydrolysis of 10 gives R(F)COCFHCOOEt.

  DOI：

  10.1021/jo00001a052

文献信息

• An expedient synthesis of α-fluoro-β-ketoesters
  作者：Alagappan Thenappan、Donald J. Burton

  DOI：10.1016/s0040-4039(01)93318-0

  日期：——
• THENAPPAN, ALAGAPPAN;BURTON, DONALD J., J. ORG. CHEM., 56,(1991) N, C. 273-277
  作者：THENAPPAN, ALAGAPPAN、BURTON, DONALD J.

  DOI：——

  日期：——
• Acylation of fluorocarbethoxy-substituted ylides: a simple and general route to .alpha.-fluoro .beta.-keto esters
  作者：Alagappan Thenappan、Donald J. Burton

  DOI：10.1021/jo00001a052

  日期：1991.1

  (Fluorocarbethoxymethylene)tri-n-butylphosphorane (3) reacts with acid chlorides and anhydrides to form the corresponding carbon acylated phosphonium salts 4, and hydrolysis of 4 under mild basic conditions provides RCOCFHCOOEt (8) in moderate yields. The reaction is applicable to primary, secondary, tertiary, cyclic, aromatic, and ester-substituted acid chlorides. Acylation with ethyl chloroformate and ethyl chlorothioformate leads to the diesters CFH(COOEt)2 and EtSCOCFHCOOEt. Extension of this reaction sequence to perfluorinated and partially fluorinated acid chlorides did not proceed cleanly to give the expected phosphonium salts. However, the anion derived from (EtO)2P(O)CFHC(O)OEt reacts with R(F)COCl to form the corresponding C-acylated phosphonates 10, and hydrolysis of 10 gives R(F)COCFHCOOEt.