(Z)-5-bromo-2-(4-methoxybenzylidene)benzofuran-3(2H)-one | 1097144-86-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-5-bromo-2-(4-methoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: (2Z)-5-bromo-2-[(4-methoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 1097144-86-9
• 化学式: C₁₆H₁₁BrO₃
• 分子量: 331.166
• InChiKey: XKJSSWKYGXXJBE-NVNXTCNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(Z)-5-bromo-2-(4-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol	1321849-10-8	C16H13BrO3	333.181

反应信息

• 作为产物：
  描述：

  4-乙炔基苯甲醚 在 manganese(IV) oxide 、 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， 生成 (Z)-5-bromo-2-(4-methoxybenzylidene)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

文献信息

• A novel cyclization/oxidation strategy for a two-step synthesis of ( Z )-aurone
  作者：Siyuan Li、Feng Jin、Mayavan Viji、Hyeju Jo、Jaeuk Sim、Hak Sung Kim、Heesoon Lee、Jae-Kyung Jung

  DOI：10.1016/j.tetlet.2017.02.074

  日期：2017.4

  An efficient and facile two-step strategy for the synthesis of (Z)-aurone from arylacetylenes and salicyladehydes, via silver(I) nitrate mediated cyclization/oxidation in the presence of potassium carbonate has been developed. The key feature of our method was delicate cascade reaction, to provide the corresponding (Z)-aurone in high yield and good regio- and stereo selectivity.

  已开发了一种有效且简便的两步策略，可在碳酸钾存在下，通过硝酸银（I）介导的环化/氧化作用，由芳基乙炔和水杨醛合成（Z）-金酮。我们方法的关键特征是精细的级联反应，以高收率和良好的区域和立体选择性提供相应的（Z）-aurone。