ethyl 5-phenyl-2-(2'-thiopyridyl)-2-trifluoroacetoxy pentanoate | 145144-78-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 5-phenyl-2-(2'-thiopyridyl)-2-trifluoroacetoxy pentanoate
• 英文别名: Ethyl 5-phenyl-2-pyridin-2-ylsulfanyl-2-(2,2,2-trifluoroacetyl)oxypentanoate
• CAS: 145144-78-1
• 化学式: C₂₀H₂₀F₃NO₄S
• 分子量: 427.444
• InChiKey: YYASHKGWRKKPFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 5-phenyl-2-(2'-thiopyridyl)-2-trifluoroacetoxy pentanoate 在 lithium aluminium tetrahydride 作用下， 以98%的产率得到5-phenyl-1,2-pentanediol
  参考文献：
  名称：

  基于Barton-酯基自由基化学的羧酸链延长和降解

  摘要：

  α-三氟乙酰氧基丙烯酸酯和丙烯腈与选自羧酸形成的碳自由基的反应给出了可以转化成加合物VIC -diols，酯，酰胺，和homoaldehydes以良好至高产率。使用自由基化学可以将醛糖平稳地降解为相应的nor-或bis-nor化合物。

  DOI：

  10.1016/0040-4039(93)88090-6
• 作为产物：
  描述：

  3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 5-phenyl-2-(2'-thiopyridyl)-2-trifluoroacetoxy pentanoate
  参考文献：
  名称：

  Two carbon homologation of carboxylic acids via carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone: Synthesis of Cn+2 α-keto-acids from Cn acids. (The ‘three carbon’ problem).

  摘要：

  Reaction of olefins containing a three carbon atom chain with carbon radicals generated from carboxylic acids furnishes adducts that are precursors of the corresponding two carbon atom longer alpha-keto-acids. The keto-acids are furnishes in high overall yield.

  DOI：

  10.1016/s0040-4039(00)61177-2

文献信息

• The invention of radical reactions. Part XXXIV. Homologation of carboxylic acids to α-keto carboxylic acids by Barton-ester based radical chain chemistry
  作者：Derek H.R. Barton、Ching-Yuh Chern、Joseph Cs. Jaszberenyi

  DOI：10.1016/0040-4020(94)01054-4

  日期：1995.2

  Carboxylic acids can be transformed into the homologous α-keto acids by Barton-ester based radical chemistry. This method was especially successful when ethyl α-trifluoroacetoxy acrylate was used as a radical trap.

  可以通过基于Barton-ester的自由基化学方法将羧酸转化为同源的α-酮酸。当使用α-三氟乙酰氧基丙烯酸乙酯作为自由基阱时，该方法特别成功。
• Two carbon homologation of carboxylic acids via carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone: Synthesis of Cn+2 α-keto-acids from Cn acids. (The ‘three carbon’ problem).
  作者：Derek H.R. Barton、Chern Ching-Yuh、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4039(00)61177-2

  日期：1992.8

  Reaction of olefins containing a three carbon atom chain with carbon radicals generated from carboxylic acids furnishes adducts that are precursors of the corresponding two carbon atom longer alpha-keto-acids. The keto-acids are furnishes in high overall yield.
• Chain-elongation and degradation of carboxylic acids by barton-ester based radical chemistry
  作者：Derek H.R. Barton、Ching-Yuh Chern、Joseph Cs. Jaszberenyi、Tetsuro Shinada

  DOI：10.1016/0040-4039(93)88090-6

  日期：1993.10

  The reaction of α-trifluoroacetoxy acrylates and acrylonitriles with carbon radicals formed from carboxylic acids gives adducts that can be transformed into vic-diols, esters, amides, and homoaldehydes in good to high yield. Aldoses can be smoothly degraded to the corresponding nor- or bis-nor compounds using radical chemistry.

  α-三氟乙酰氧基丙烯酸酯和丙烯腈与选自羧酸形成的碳自由基的反应给出了可以转化成加合物VIC -diols，酯，酰胺，和homoaldehydes以良好至高产率。使用自由基化学可以将醛糖平稳地降解为相应的nor-或bis-nor化合物。