methyl 5-(2-chlorophenyl)-3,5-dioxopentanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-(2-chlorophenyl)-3,5-dioxopentanoate
• 英文别名: methyl 5-(o-chlorophenyl)-3,5-dioxopentanoate；Methyl 5-(2-chlorophenyl)-3,5-dioxopentanoate
• 化学式: C₁₂H₁₁ClO₄
• 分子量: 254.67
• InChiKey: GZIZODXXDGAJQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(2-chlorophenyl)-3,5-dioxopentanoate 、 碘甲烷 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.5h， 以65%的产率得到methyl 5-(2-chlorophenyl)-2,2,4,4-tetramethyl-3,5-dioxopentanoate
  参考文献：
  名称：

  Synthesis and characterization of permethylated 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds

  摘要：

  Permethylated 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds were prepared and structurally characterized. 2,2,4,4-Tetramethyl-3,5-dioxoesters were prepared by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with acid chlorides and subsequent reaction with methyl iodide. 2,2,4,4,6,6-Hexa-substituted 3,5-dioxopimelates were prepared by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with methyl 3-chloro-3-oxopropanoate and subsequent methylation. The use of caesium carbonate as the base for the methylation proved to be important to achieve good yields. The conformation of the products was studied by experimental and theoretical methods (DFT calculations). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.065
• 作为产物：
  描述：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 、 邻氯苯甲酰氯 以 二氯甲烷 为溶剂， 以59%的产率得到methyl 5-(2-chlorophenyl)-3,5-dioxopentanoate
  参考文献：
  名称：

  1,3-双（甲硅烷基烯醇醚）与酰氯的缩合反应合成1,3,5-三羰基衍生物

  摘要：

  在温和的条件下，通过1,3-双（甲硅烷基烯醇醚）与酰氯的反应，可以制得各种1,3,5-三羰基衍生物。这包括芳族和脂族酰氯与双（酰氯）的反应。收率根据所用酰氯的类型而变化。

  DOI：

  10.1021/jo062153w

文献信息

• Synthesis of 1,3,5-Tricarbonyl Derivatives by Condensation of 1,3-Bis(silyl enol ethers) with Acid Chlorides
  作者：Thomas Rahn、Van T. H. Nguyen、T. H. Tam Dang、Zafar Ahmed、Karen Methling、Michael Lalk、Christine Fischer、Anke Spannenberg、Peter Langer

  DOI：10.1021/jo062153w

  日期：2007.3.1

  A variety of 1,3,5-tricarbonyl derivatives were prepared by reaction of 1,3-bis(silyl enol ethers) with acid chlorides under mild conditions. This includes reactions of both aromatic and aliphatic acid chlorides and bis(acid chlorides). The yields vary depending on the type of acid chloride employed.

  在温和的条件下，通过1,3-双（甲硅烷基烯醇醚）与酰氯的反应，可以制得各种1,3,5-三羰基衍生物。这包括芳族和脂族酰氯与双（酰氯）的反应。收率根据所用酰氯的类型而变化。
• Synthesis and characterization of permethylated 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds
  作者：Silke Erfle、Thomas Rahn、Franziska Bendrath、Wolfgang Baumann、Dirk Michalik、Haijun Jiao、Anke Spannenberg、Armin Börner、Peter Langer

  DOI：10.1016/j.tet.2011.08.065

  日期：2011.11

  Permethylated 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds were prepared and structurally characterized. 2,2,4,4-Tetramethyl-3,5-dioxoesters were prepared by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with acid chlorides and subsequent reaction with methyl iodide. 2,2,4,4,6,6-Hexa-substituted 3,5-dioxopimelates were prepared by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with methyl 3-chloro-3-oxopropanoate and subsequent methylation. The use of caesium carbonate as the base for the methylation proved to be important to achieve good yields. The conformation of the products was studied by experimental and theoretical methods (DFT calculations). (C) 2011 Elsevier Ltd. All rights reserved.