4-hydroxy-3-(2-chlorophenyl)coumarin | 30014-86-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4-hydroxy-3-(2-chlorophenyl)coumarin
• 英文别名: 3-(2-chloro-phenyl)-4-hydroxy-chromen-2-one；3-(2-Chlorophenyl)-4-hydroxychromen-2-one
• CAS: 30014-86-9
• 化学式: C₁₅H₉ClO₃
• 分子量: 272.688
• InChiKey: TTXSGJJPITZRHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 1-氯-2-碘苯 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以23%的产率得到4-hydroxy-3-(2-chlorophenyl)coumarin
  参考文献：
  名称：

  A different route to 3-aryl-4-hydroxycoumarins

  摘要：

  We herein report the simple and direct arylation of 4-hydroxycoumarins by photoinduced reaction with aryl halides (iodobenzene, iodonaphthalene, 4-iodoanisole, 2-iodoanisole). Good yields of 3,4-disubstituted coumarins were obtained in these reactions (>60%). Extension of the procedure to the reaction with o-dihalobenzenes leads to the synthesis of ring closure products which bear a tetracyclic aromatic-condensed ring system, although in lower overall yields (approximate to 45%). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.013

文献信息

• A different route to 3-aryl-4-hydroxycoumarins
  作者：Sergio A. Rodríguez、Maria T. Baumgartner

  DOI：10.1016/j.tetlet.2010.08.013

  日期：2010.10

  We herein report the simple and direct arylation of 4-hydroxycoumarins by photoinduced reaction with aryl halides (iodobenzene, iodonaphthalene, 4-iodoanisole, 2-iodoanisole). Good yields of 3,4-disubstituted coumarins were obtained in these reactions (>60%). Extension of the procedure to the reaction with o-dihalobenzenes leads to the synthesis of ring closure products which bear a tetracyclic aromatic-condensed ring system, although in lower overall yields (approximate to 45%). (C) 2010 Elsevier Ltd. All rights reserved.