2-[((E)-But-2-enyl)oxy]-3,3-difluoro-acrylic acid ethyl ester | 1027155-59-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-[((E)-But-2-enyl)oxy]-3,3-difluoro-acrylic acid ethyl ester
• 英文别名: ethyl 2-[(E)-but-2-enoxy]-3,3-difluoroprop-2-enoate
• CAS: 1027155-59-4
• 化学式: C₉H₁₂F₂O₃
• 分子量: 206.189
• InChiKey: PPBMDPCWHVQBFC-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[((E)-But-2-enyl)oxy]-3,3-difluoro-acrylic acid ethyl ester 以 苯 为溶剂， 反应 1.0h， 生成 ethyl 2,2-difluoro-4-methyl-2-oxo-5-hexenoate
  参考文献：
  名称：

  .delta.,.epsilon.-Unsaturated .beta.,.beta.-Difluoro-.alpha.-keto Esters: Novel Synthesis and Utility as Precursors of .beta.,.beta.-Difluoro-.alpha.-amino Acids

  摘要：

  Treatment of the hemiketals 6 formed from ethyl trifluoropyruvate and primary allylic alcohols with SOCl2 and pyridine readily afforded a number of alpha-chloro-beta,beta,beta-trifluorolactyl allyl ethers 2. Subsequent reductive dechlorofluorination from 2 led to the formation of allyl-substituted difluoroenol pyruvyl ethers 3 whose Claisen rearrangement provided a convenient access to a variety of delta,epsilon-unsaturated beta,beta-difluoro-alpha-keto esters 4. As further transformation, direct conversion of beta,beta-difluoro-alpha-keto esters to the corresponding beta,beta-difluoro-alpha-amino acids was achieved by reductive amination of the corresponding alpha-keto acids with NH3 . H2O/NaBH4. Furthermore, use of the prepared beta beta-difluoro-alpha-keto ester 4a as a common precursor of other structurally related beta,beta-difluoro-alpha-amino acids was demonstrated by the synthesis of beta,beta-difluoroproline (18) and beta,beta-difluoroglutamic acid (23) through synthetic elaboration of its inherent double bond.

  DOI：

  10.1021/jo00125a013
• 作为产物：
  描述：

  3,3,3-三氟丙酮酸乙酯 在 copper(l) iodide 、 氯化亚砜 、 锌 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.0h， 生成 2-[((E)-But-2-enyl)oxy]-3,3-difluoro-acrylic acid ethyl ester
  参考文献：
  名称：

  .delta.,.epsilon.-Unsaturated .beta.,.beta.-Difluoro-.alpha.-keto Esters: Novel Synthesis and Utility as Precursors of .beta.,.beta.-Difluoro-.alpha.-amino Acids

  摘要：

  Treatment of the hemiketals 6 formed from ethyl trifluoropyruvate and primary allylic alcohols with SOCl2 and pyridine readily afforded a number of alpha-chloro-beta,beta,beta-trifluorolactyl allyl ethers 2. Subsequent reductive dechlorofluorination from 2 led to the formation of allyl-substituted difluoroenol pyruvyl ethers 3 whose Claisen rearrangement provided a convenient access to a variety of delta,epsilon-unsaturated beta,beta-difluoro-alpha-keto esters 4. As further transformation, direct conversion of beta,beta-difluoro-alpha-keto esters to the corresponding beta,beta-difluoro-alpha-amino acids was achieved by reductive amination of the corresponding alpha-keto acids with NH3 . H2O/NaBH4. Furthermore, use of the prepared beta beta-difluoro-alpha-keto ester 4a as a common precursor of other structurally related beta,beta-difluoro-alpha-amino acids was demonstrated by the synthesis of beta,beta-difluoroproline (18) and beta,beta-difluoroglutamic acid (23) through synthetic elaboration of its inherent double bond.

  DOI：

  10.1021/jo00125a013

文献信息

• .delta.,.epsilon.-Unsaturated .beta.,.beta.-Difluoro-.alpha.-keto Esters: Novel Synthesis and Utility as Precursors of .beta.,.beta.-Difluoro-.alpha.-amino Acids
  作者：Guo-qiang Shi、Wei-ling Cai

  DOI：10.1021/jo00125a013

  日期：1995.10

  Treatment of the hemiketals 6 formed from ethyl trifluoropyruvate and primary allylic alcohols with SOCl2 and pyridine readily afforded a number of alpha-chloro-beta,beta,beta-trifluorolactyl allyl ethers 2. Subsequent reductive dechlorofluorination from 2 led to the formation of allyl-substituted difluoroenol pyruvyl ethers 3 whose Claisen rearrangement provided a convenient access to a variety of delta,epsilon-unsaturated beta,beta-difluoro-alpha-keto esters 4. As further transformation, direct conversion of beta,beta-difluoro-alpha-keto esters to the corresponding beta,beta-difluoro-alpha-amino acids was achieved by reductive amination of the corresponding alpha-keto acids with NH3 . H2O/NaBH4. Furthermore, use of the prepared beta beta-difluoro-alpha-keto ester 4a as a common precursor of other structurally related beta,beta-difluoro-alpha-amino acids was demonstrated by the synthesis of beta,beta-difluoroproline (18) and beta,beta-difluoroglutamic acid (23) through synthetic elaboration of its inherent double bond.