methyl 5-(2,6-difluorophenyl)-2,2,4,4-tetramethyl-3,5-dioxopentanoate | 1345013-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-(2,6-difluorophenyl)-2,2,4,4-tetramethyl-3,5-dioxopentanoate
• CAS: 1345013-83-3
• 化学式: C₁₆H₁₈F₂O₄
• 分子量: 312.313
• InChiKey: SQNJGFJOSKGNAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl 5-(2,6-difluorophenyl)-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31%的产率得到methyl 5-(2,6-difluorophenyl)-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

文献信息

• 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.