(Z)-5-bromo-2-(4-methylbenzylidene)-2,3-dihydrobenzofuran-3-ol | 1262020-41-6

• 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: (Z)-5-bromo-2-(4-methylbenzylidene)-2,3-dihydrobenzofuran-3-ol
• 英文别名: (2Z)-5-bromo-2-[(4-methylphenyl)methylidene]-3H-1-benzofuran-3-ol
• CAS: 1262020-41-6
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: FRRYUVYURMADHA-NVNXTCNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-bromo-2-(4-methylbenzylidene)-2,3-dihydrobenzofuran-3-ol 在 manganese(IV) oxide 作用下， 以 甲苯 为溶剂， 生成 (Z)-5-bromo-2-(4-methylbenzylidene)benzofuran-3(2H)-one
  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
• 作为产物：
  描述：

  4-Bromo-2-[1-hydroxy-3-(4-methylphenyl)prop-2-ynyl]phenol 在 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 水 、 甲苯 为溶剂， 反应 1.5h， 以85%的产率得到(Z)-5-bromo-2-(4-methylbenzylidene)-2,3-dihydrobenzofuran-3-ol
  参考文献：
  名称：

  Ligand-promoted reaction on silver nanoparticles: phosphine-promoted, silver nanoparticle-catalyzed cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols

  摘要：

  A highly efficient annulation of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols leading to the key intermediates to synthesize aurones was catalyzed by silver nanoparticles/carbon black-supported silver nanoparticles. In the presence of phosphine ligand, both the catalysts show excellent catalytic activities in the reaction and give the products with good yields as well as excellent regio- and stereo-selectivities in a water-toluene mixed solvent. Furthermore, the catalysts can be recovered and recycled effectively several times. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.065

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.