2-(2-bromo-3,5-dimethoxyphenyl)-6-methoxybenzofuran | 936856-32-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(2-bromo-3,5-dimethoxyphenyl)-6-methoxybenzofuran
• 英文别名: 2-(2-Bromo-3,5-dimethoxyphenyl)-6-methoxy-1-benzofuran
• CAS: 936856-32-5
• 化学式: C₁₇H₁₅BrO₄
• 分子量: 363.208
• InChiKey: CFWAMSQLRIGVRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-3,5-dimethoxyphenyl)-6-methoxybenzofuran 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 正丁基锂 、 二苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Demethylmoracin I
  参考文献：
  名称：

  Nucleophilic Acylation of o-Quinone Methides:  An Umpolung Strategy for the Synthesis of α-Aryl Ketones and Benzofurans

  摘要：

  The synthesis of alpha-aryl ketones is accomplished by the direct nucleophilic acylation of o-quinone methide electrophiles. In this process, two reactive intermediates, carbonyl anions and o-quinone methides, are generated in one flask upon treatment of the corresponding thiazolium carbinols and silyl protected phenols with a soluble fluoride source. These intermediates then undergo productive addition reactions to afford the desired alpha-aryl ketone adducts. This new strategy has been applied to a short synthesis of the natural product demethylmoracin I.

  DOI：

  10.1021/ja068189n
• 作为产物：
  描述：

  tert-butyl(2-(chloromethyl)-5-methoxyphenoxy)dimethylsilane 在 Amberlyst 15 、 4 A molecular sieve 、 四甲基氟化铵 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-bromo-3,5-dimethoxyphenyl)-6-methoxybenzofuran
  参考文献：
  名称：

  Nucleophilic Acylation of o-Quinone Methides:  An Umpolung Strategy for the Synthesis of α-Aryl Ketones and Benzofurans

  摘要：

  The synthesis of alpha-aryl ketones is accomplished by the direct nucleophilic acylation of o-quinone methide electrophiles. In this process, two reactive intermediates, carbonyl anions and o-quinone methides, are generated in one flask upon treatment of the corresponding thiazolium carbinols and silyl protected phenols with a soluble fluoride source. These intermediates then undergo productive addition reactions to afford the desired alpha-aryl ketone adducts. This new strategy has been applied to a short synthesis of the natural product demethylmoracin I.

  DOI：

  10.1021/ja068189n