(6-chloro-2-oxo-2H-chromen-3-yl)acetic acid methyl ester | 1005328-56-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (6-chloro-2-oxo-2H-chromen-3-yl)acetic acid methyl ester
• 英文别名: Methyl 2-(6-chloro-2-oxochromen-3-yl)acetate
• CAS: 1005328-56-2
• 化学式: C₁₂H₉ClO₄
• 分子量: 252.654
• InChiKey: LQRHKZHWYCPFGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 一氧化碳 、 4-chloro-2-(1-hydroxyprop-2-ynyl)phenol 在 palladium(II) iodide potassium iodide 作用下， 25.0 ℃ 、9.12 MPa 条件下， 反应 15.0h， 以74%的产率得到(6-chloro-2-oxo-2H-chromen-3-yl)acetic acid methyl ester
  参考文献：
  名称：

  A Novel Palladium-Catalyzed Dicarbonylation Process Leading to Coumarins

  摘要：

  [GRAPHICS]A novel approach to coumarin derivatives has been developed starting from readily available 2-(1-hydroxyprop-2-ynyl)phenols, based on an unprecedented palladium-catalyzed dicarbonylation process. Reactions were carried out in the presence of catalytic amounts of PdI2 in conjunction with an excess of KI in MeOH as the solvent at room temperature and under 90 atm of CO to give 3-[(methoxycarbonyl)-methyl]coumarins in good to high isolated yields (62-87%).

  DOI：

  10.1021/jo702243m

文献信息

• A Novel Palladium-Catalyzed Dicarbonylation Process Leading to Coumarins
  作者：Bartolo Gabriele、Raffaella Mancuso、Giuseppe Salerno、Pierluigi Plastina

  DOI：10.1021/jo702243m

  日期：2008.1.1

  [GRAPHICS]A novel approach to coumarin derivatives has been developed starting from readily available 2-(1-hydroxyprop-2-ynyl)phenols, based on an unprecedented palladium-catalyzed dicarbonylation process. Reactions were carried out in the presence of catalytic amounts of PdI2 in conjunction with an excess of KI in MeOH as the solvent at room temperature and under 90 atm of CO to give 3-[(methoxycarbonyl)-methyl]coumarins in good to high isolated yields (62-87%).