(Z)-2-(4-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol | 1008105-84-7

• 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)-2-(4-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol
• 英文别名: (2Z)-2-[(4-methoxyphenyl)methylidene]-3H-1-benzofuran-3-ol
• CAS: 1008105-84-7
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: BLWISEIFCVDPCD-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol 在 manganese(IV) oxide 作用下， 以 甲苯 为溶剂， 生成 (Z)-4'-methoxyaurone
  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：

  (Z)-4'-methoxyaurone 在 sodium tetrahydroborate 、 水 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 (Z)-2-(4-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol
  参考文献：
  名称：

  A straightforward conversion of aurones to 2-benzoylbenzofurans: transformation of one class of natural products into another

  摘要：

  The naturally occurring aurones (2-benzylidene-3(2H)-benzofuran-3-ones) can be easily converted to another class of natural products 2-benzoylbenzo[b]furans, via an effective reduction, acid-mediated rearrangement, and oxidation cascade. This easy conversion was conducted without purification of intermediates. This straightforward conversion may be considered as a possible biosynthesis pathway of 2-benzoylbenzo[b]furans in plants. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.011

文献信息

• Versatile and Expeditious Synthesis of Aurones via Au^I-Catalyzed Cyclization
  作者：Hassina Harkat、Aurélien Blanc、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo702197b

  日期：2008.2.1

  Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3‘,4‘-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4‘-chloroaurone)

  可以以三步程序方便地形成Aurones，包括金I催化的2-（1-羟基丙-2-炔基）苯酚的环化反应，这是高度区域选择性和立体选择性的关键步骤。从取代的水杨醛开始可以得到各种各样的衍生物。实现了天然4,6,3'，4'-四甲氧基金龙的合成和两种天然产物（dalmaisione D和4'-氯金龙）的结构修饰。
• 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.
• 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
  作者：Mingdeng Lin、Min Yu、Chengyan Han、Chao-Jun Li、Xiaoquan Yao

  DOI：10.1080/00397911.2010.517613

  日期：2011.11.1

  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.
• A straightforward conversion of aurones to 2-benzoylbenzofurans: transformation of one class of natural products into another
  作者：Samir Yahiaoui、Marine Peuchmaur、Ahcène Boumendjel

  DOI：10.1016/j.tet.2011.08.011

  日期：2011.10

  The naturally occurring aurones (2-benzylidene-3(2H)-benzofuran-3-ones) can be easily converted to another class of natural products 2-benzoylbenzo[b]furans, via an effective reduction, acid-mediated rearrangement, and oxidation cascade. This easy conversion was conducted without purification of intermediates. This straightforward conversion may be considered as a possible biosynthesis pathway of 2-benzoylbenzo[b]furans in plants. (C) 2011 Elsevier Ltd. All rights reserved.