3,3,3-Trifluoro-2-[((E)-hex-2-enyl)oxy]-2-hydroxy-propionic acid ethyl ester | 1027536-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,3-Trifluoro-2-[((E)-hex-2-enyl)oxy]-2-hydroxy-propionic acid ethyl ester
• 英文别名: ethyl 3,3,3-trifluoro-2-[(E)-hex-2-enoxy]-2-hydroxypropanoate
• CAS: 1027536-14-6
• 化学式: C₁₁H₁₇F₃O₄
• 分子量: 270.249
• InChiKey: FHBVEXZXSUYFMN-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,3,3-Trifluoro-2-[((E)-hex-2-enyl)oxy]-2-hydroxy-propionic acid ethyl ester 在 氯化亚砜 作用下， 以 吡啶 、 苯 为溶剂， 反应 0.5h， 生成 ethyl 2-<(E)-2-hexenyloxy>-2-chloro-3,3,3-trifluoropropanoate
  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：

  反式-2-已烯-1-醇 、 3,3,3-三氟丙酮酸乙酯 以 苯 为溶剂， 反应 0.5h， 生成 3,3,3-Trifluoro-2-[((E)-hex-2-enyl)oxy]-2-hydroxy-propionic 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.