(E)-2-benzylidene-2,3-dihydrobenzofuran-3-ol | 1147869-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (E)-2-benzylidene-2,3-dihydrobenzofuran-3-ol
• 英文别名: (2E)-2-benzylidene-3H-1-benzofuran-3-ol
• CAS: 1147869-68-8
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: FTZSRGNLHPVEHB-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol 在 silver fluoride 、 N,N-二异丙基乙胺 、 三环己基膦 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以81%的产率得到(E)-2-benzylidene-2,3-dihydrobenzofuran-3-ol
  参考文献：
  名称：

  Water-Promoted, Silver–Phosphine Complex–Catalyzed Stereoselective Cyclization of 2-(1-Hydroxy-3-arylprop-2-ynyl)phenols Leading to a Highly Efficient Approach to Aurones

  摘要：

  Silver-phosphine complexes can be utilized as highly efficient catalysts for the cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols (1) to give product 2, key intermediates to synthesize aurones (4), with good yields and stereoselectivities in water-toluene mixed solvent. With fluoride as the counteranion, complete E- or Z-stereoselectivities were achieved at high temperature or room temperature, respectively. Furthermore, after removing water from the reaction mixtures, the toluene solution containing crude products 2 can be treated by MnO2 directly without further purification, to give aurones 4 in good yields.

  DOI：

  10.1080/00397911.2010.517613

文献信息

• Water-Triggered, Counter-Anion-Controlled, and Silver−Phosphines Complex-Catalyzed Stereoselective Cascade Alkynylation/Cyclization of Terminal Alkynes with Salicylaldehydes
  作者：Min Yu、Rachid Skouta、Lei Zhou、Huan-feng Jiang、Xiaoquan Yao、Chao-Jun Li

  DOI：10.1021/jo900079u

  日期：2009.5.1

  A highly efficient alkynylation-cyclization of terminal alkynes with salicylaldehydes leading to substituted 2,3-dihydrobenzofuran-3-ol derivatives was developed by using Cy3P-silver complex as catalyst in water. Counter anions in the silver complex proved to be the key factor to Z/E stereoselectivity control. Aurones can also be obtained effectively from the cascade reaction followed by oxidation without further purification.