methyl 5-phenyl-2-(pyridine-2'-sulfinyl)pentanoate | 163975-27-7

• 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: methyl 5-phenyl-2-(pyridine-2'-sulfinyl)pentanoate
• 英文别名: Methyl 5-phenyl-2-pyridin-2-ylsulfinylpentanoate；methyl 5-phenyl-2-pyridin-2-ylsulfinylpentanoate
• CAS: 163975-27-7
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: ZTXKJGLYUKNWBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-phenyl-2-(pyridine-2'-sulfinyl)pentanoate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-氧代-5-苯基戊酸
  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
• 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 methyl 5-phenyl-2-(pyridine-2'-sulfinyl)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。