2-(2-allyl-3,4-dimethoxyphenoxy)-1-(p-tolyl)ethanone | 1194403-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-allyl-3,4-dimethoxyphenoxy)-1-(p-tolyl)ethanone
• CAS: 1194403-18-3
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: LFXHCJHRVVAPCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-allyl-3,4-dimethoxyphenoxy)-1-(p-tolyl)ethanone 在 potassium tert-butylate 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 以64%的产率得到trans-2-(4-methylbenzoyl)-5,6-dimethoxy-3-methylchroman
  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
• 作为产物：
  描述：

  3,4-二甲氧基-2-(2-丙烯基)苯酚 、 2-溴-4'-甲基苯乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以93%的产率得到2-(2-allyl-3,4-dimethoxyphenoxy)-1-(p-tolyl)ethanone
  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

文献信息

• Synthesis of substituted 2-aroyl-3-methylchromen-4-ones from isovanillin via 2-aroyl-3-methylchroman intermediates
  作者：Sie-Rong Li、Chung-Jung Shu、Liang-Yeu Chen、Hsing-Ming Chen、Po-Yuan Chen、Eng-Chi Wang

  DOI：10.1016/j.tet.2009.08.043

  日期：2009.10

  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.