(2S,3R)-2-(3,4-Dimethoxy-phenyl)-4-[(R)-(E)-indan-1-yliminomethyl]-7-methoxy-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester | 868258-27-9

• 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: (2S,3R)-2-(3,4-Dimethoxy-phenyl)-4-[(R)-(E)-indan-1-yliminomethyl]-7-methoxy-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester
• CAS: 868258-27-9
• 化学式: C₂₉H₂₉NO₆
• 分子量: 487.552
• InChiKey: GBZJVZVMQQPHAN-LSIHIPAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  75.58
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(3,4-Dimethoxy-phenyl)-4-[(R)-(E)-indan-1-yliminomethyl]-7-methoxy-2,3-dihydro-benzofuran-3-carboxylic acid methyl ester 在 盐酸 作用下， 反应 0.33h， 以1.34 g的产率得到2-(3,4-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
• 作为产物：
  描述：

  methyl 3-(3,4-dimethoxyphenyl)propiolate 在 1-di(2-(5-methylfuryl)phosphanyl)ferrocene 、 [RhCl(coe)2]2 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 反应 35.83h， 生成 (2S,3R)-2-(3,4-Dimethoxy-phenyl)-4-[(R)-(E)-indan-1-yliminomethyl]-7-methoxy-2,3-dihydro-benzofuran-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