1-(5-hydroxy-2-phenylbenzofuran-3-yl)ethanone | 1221190-19-7

• 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: 1-(5-hydroxy-2-phenylbenzofuran-3-yl)ethanone
• 英文别名: 1-(5-Hydroxy-2-phenyl-1-benzofuran-3-yl)ethanone；1-(5-hydroxy-2-phenyl-1-benzofuran-3-yl)ethanone
• CAS: 1221190-19-7
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: KGHUBLQAVVFXEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-hydroxyl-2-(methylthio)-3-acetylbenzofuran 、 苯硼酸 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以85%的产率得到1-(5-hydroxy-2-phenylbenzofuran-3-yl)ethanone
  参考文献：
  名称：

  Pd-Catalyzed C–S Activation for [3 + 3] Annulation of 2-(Methylthio)benzofuran-3-carboxylates and 2-Hydroxyphenylboronic Acids: Synthesis of Coumestan Derivatives

  摘要：

  Pd-catalytic C-S activation was successfully applied to initiate the cross-coupling of (2-methylthio-3-ester)benzofurans with 2-hydroxyphenylboronic acids and sequential intramolecular transesterification process under Liebeskind-Srogl conditions. Thus, a novel [3 + 3] annulation strategy for efficient synthesis of coumestan derivatives has been developed from readily available starting materials.

  DOI：

  10.1021/jo400984h

文献信息

• Thirupathaiah; Venkateshwar Rao; Ramanna, Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1521 - 1524
  作者：Thirupathaiah、Venkateshwar Rao、Ramanna

  DOI：——

  日期：——
• Efficient synthesis of 3-acyl-5-hydroxybenzofurans via copper(II) triflate-catalyzed cycloaddition of unactivated 1,4-benzoquinones with 1,3-dicarbonyl compounds
  作者：Srinivasa Reddy Mothe、Dewi Susanti、Philip Wai Hong Chan

  DOI：10.1016/j.tetlet.2010.02.066

  日期：2010.4

  A method to prepare a variety of substituted 3-acyl-5-hydroxybenzofurans efficiently that relies on copper(II) triflate-catalyzed cycloaddition of unactivated 1,4-benzoquinones with 1,3-dicarbonyl compounds is reported. The reaction was shown to be operationally straightforward and proceeds expediently under mild conditions to give the corresponding products in good to excellent yields (up to 95%) and with complete regioselectivity. (c) 2010 Elsevier Ltd. All rights reserved.