ethyl 2,6-dimethyl-4-oxochroman-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 2,6-dimethyl-4-oxochroman-2-carboxylate
• 英文别名: ethyl 2,6-dimethyl-4-oxo-3H-chromene-2-carboxylate
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: BOEZXTMQKKPYMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 6-methyl-4-oxochroman-2-carboxylate 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以86%的产率得到ethyl 2,6-dimethyl-4-oxochroman-2-carboxylate
  参考文献：
  名称：

  Unprecedented C-Methylation at the 2-Position of 2-Carboxy-4-Chromanones – A Case Study with the Corey–Chaykovsky Reagent

  摘要：

  An unprecedented C-methylation at the 2-position of 4-chromanone-2-carboxylates was achieved in good yield on treatment with dimethylsulfoxonium methylide. The reaction was performed with excellent chemo- as well as regioselectivity. It is the first synthetic report of alkylation at the 2-position of the chromanone framework through a very mild and simple approach. Such an uncommon behavioral pattern of the Corey-Chaykovsky reagent is justified by theoretical potential energy surface calculations.

  DOI：

  10.1055/s-0034-1379203