methyl 3-oxo-2-(4'-isobutyl)phenylbutanoate | 172160-07-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 3-oxo-2-(4'-isobutyl)phenylbutanoate
• 英文别名: Methyl 2-[4-(2-methylpropyl)phenyl]-3-oxobutanoate
• CAS: 172160-07-5
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: AYANBIJLPYFFAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-oxo-2-(4'-isobutyl)phenylbutanoate 在 potassium tert-butylate 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以58%的产率得到2-(4-Isobutyl-phenyl)-2-methyl-3-oxo-butyric acid methyl ester
  参考文献：
  名称：

  A study on the mechanism and scope of the radical-mediated oxidation of arylacetoacetates

  摘要：

  Arylacetoacetate 1a undergoes an oxidative degradation in the presence of K(t)BuO, THF, catalytic I-2 and O-2, to give keto ester 4 as major compound. Hydrolysis and decarboxylation of this intermediate led to the corresponding arylcarboxylic acid 3a in satisfactory overall yields. By experiments conducted in the presence of O-18(2), incorporation of atmosphere oxygen into the benzylic position of 4 was evidenced. Furthermore, spin-trap experiments showed that benzyl radical 7 was generated in the reaction medium, which supports its role as intermediate in the pathway leading to the observed oxidation products. A plausible mechanism for this process is presented. On the other hand, appropriate conditions for achieving the alkylation of these arylacetoacetates with no concomitant formation of oxidation side-products are reported. Finally, arylacetates suffer also this degradative oxidation process leading to the corresponding arylcarboxylic acids without isolation of the intermediate keto ester derivative.

  DOI：

  10.1016/0040-4020(95)00576-t
• 作为产物：
  描述：

  methyl 3-oxo-2-(4'-isobutyryl)phenylbutanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、392.24 kPa 条件下， 反应 9.0h， 以82%的产率得到methyl 3-oxo-2-(4'-isobutyl)phenylbutanoate
  参考文献：
  名称：

  A study on the mechanism and scope of the radical-mediated oxidation of arylacetoacetates

  摘要：

  Arylacetoacetate 1a undergoes an oxidative degradation in the presence of K(t)BuO, THF, catalytic I-2 and O-2, to give keto ester 4 as major compound. Hydrolysis and decarboxylation of this intermediate led to the corresponding arylcarboxylic acid 3a in satisfactory overall yields. By experiments conducted in the presence of O-18(2), incorporation of atmosphere oxygen into the benzylic position of 4 was evidenced. Furthermore, spin-trap experiments showed that benzyl radical 7 was generated in the reaction medium, which supports its role as intermediate in the pathway leading to the observed oxidation products. A plausible mechanism for this process is presented. On the other hand, appropriate conditions for achieving the alkylation of these arylacetoacetates with no concomitant formation of oxidation side-products are reported. Finally, arylacetates suffer also this degradative oxidation process leading to the corresponding arylcarboxylic acids without isolation of the intermediate keto ester derivative.

  DOI：

  10.1016/0040-4020(95)00576-t

文献信息

• A study on the mechanism and scope of the radical-mediated oxidation of arylacetoacetates
  作者：Mercè Tona、Marisa Guardiola、Lluis Fajarí、Angel Messeguer

  DOI：10.1016/0040-4020(95)00576-t

  日期：1995.1

  Arylacetoacetate 1a undergoes an oxidative degradation in the presence of K(t)BuO, THF, catalytic I-2 and O-2, to give keto ester 4 as major compound. Hydrolysis and decarboxylation of this intermediate led to the corresponding arylcarboxylic acid 3a in satisfactory overall yields. By experiments conducted in the presence of O-18(2), incorporation of atmosphere oxygen into the benzylic position of 4 was evidenced. Furthermore, spin-trap experiments showed that benzyl radical 7 was generated in the reaction medium, which supports its role as intermediate in the pathway leading to the observed oxidation products. A plausible mechanism for this process is presented. On the other hand, appropriate conditions for achieving the alkylation of these arylacetoacetates with no concomitant formation of oxidation side-products are reported. Finally, arylacetates suffer also this degradative oxidation process leading to the corresponding arylcarboxylic acids without isolation of the intermediate keto ester derivative.