2-(2-bromo-4,5-dimethoxyphenyl)-4-formyl-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid methyl ester | 868258-17-7

• 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-4,5-dimethoxyphenyl)-4-formyl-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid methyl ester
• CAS: 868258-17-7
• 化学式: C₂₀H₁₉BrO₇
• 分子量: 451.271
• InChiKey: WTCCUGMAAWGXRA-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-4,5-dimethoxyphenyl)-4-formyl-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid methyl ester 、 2,4-二硝基苯肼 在 硫酸 作用下， 以 乙醇 为溶剂， 以59%的产率得到2-(2-bromo-4,5-dimethoxyphenyl)-4-[(2,4-dinitrophenyl)hydrazonomethyl]-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via Catalytic C−H Bond Activation

  摘要：

  The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C-H bond functionalization and represents the first application of this C-H activation method to natural product synthesis. Furthermore, a challenging deprotection of a late-stage permethylated lithospermic acid was achieved.

  DOI：

  10.1021/ja052680h
• 作为产物：
  描述：

  3-(3,4-dimethoxyphenyl)-3-[5-(indan-1-yliminomethyl)-2-methoxyphenoxy]acrylic acid methyl ester 在 盐酸 、 1-di(2-(5-methylfuryl)phosphanyl)ferrocene 、 [RhCl(coe)2]2 、 溴 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 20.66h， 生成 2-(2-bromo-4,5-dimethoxyphenyl)-4-formyl-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via Catalytic C−H Bond Activation

  摘要：

  The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C-H bond functionalization and represents the first application of this C-H activation method to natural product synthesis. Furthermore, a challenging deprotection of a late-stage permethylated lithospermic acid was achieved.

  DOI：

  10.1021/ja052680h