4-Chloro-2-(1-hydroxy-3-phenylprop-2-ynyl)-6-nitrophenol | 1262020-30-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-Chloro-2-(1-hydroxy-3-phenylprop-2-ynyl)-6-nitrophenol
• CAS: 1262020-30-3
• 化学式: C₁₅H₁₀ClNO₄
• 分子量: 303.702
• InChiKey: QYRFZTZQQSOMGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Chloro-2-(1-hydroxy-3-phenylprop-2-ynyl)-6-nitrophenol 在 tricyclohexylphosphine-silver chloride 、 N,N-二异丙基乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 1.0h， 以79%的产率得到(Z)-2-benzylidene-5-chloro-7-nitro-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
• 作为产物：
  描述：

  5-氯-3-硝基水杨醛 、 苯乙炔 生成 4-Chloro-2-(1-hydroxy-3-phenylprop-2-ynyl)-6-nitrophenol
  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

• Ligand-promoted reaction on silver nanoparticles: phosphine-promoted, silver nanoparticle-catalyzed cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols
  作者：Min Yu、Mingdeng Lin、Chengyan Han、Li Zhu、Chao-Jun Li、Xiaoquan Yao

  DOI：10.1016/j.tetlet.2010.10.065

  日期：2010.12

  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.