5,6-dimethoxy-3-methyl-2-(4-methylbenzoyl)chromen-4-one | 1194403-33-2

• 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: 5,6-dimethoxy-3-methyl-2-(4-methylbenzoyl)chromen-4-one
• CAS: 1194403-33-2
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: NXZOAPCUYVPMLE-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  2-(4-methylbenzoyl)-5,6-dimethoxy-3-methylchroman 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以60%的产率得到5,6-dimethoxy-3-methyl-2-(4-methylbenzoyl)chromen-4-one
  参考文献：
  名称：

  Synthesis of substituted 2-aroyl-3-methylchromen-4-ones from isovanillin via 2-aroyl-3-methylchroman intermediates

  摘要：

  The synthesis of Substituted 2-aroyl-3-methylchromen-4-one from isovanillin is described. O-Allylphenol (2) prepared from isovanillin (1) was allowed to react with various alpha-bromoacetophenone (3) to produce 2-(2-allyl-3,4-dimethoxy)phenoxy-1-aroylethanones (4). The resultant 4 were treated with 2 equiv of potassium tert-butoxide to afford the substituted 2-aroyl-3-methylchromans (5) through an isomerization of an allylic double bond and a carbanion-olefin intramolecular 6-endo-trig cyclization reaction. Subsequently, resultant 5 were oxidized with DDQ to yield the title compound 6, in good over-all yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.043