(Z)-2-benzylidene-2,3-dihydrobenzofuran-3-ol | 1008105-79-0

• 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-benzylidene-2,3-dihydrobenzofuran-3-ol
• 英文别名: (2Z)-2-benzylidene-3H-1-benzofuran-3-ol
• CAS: 1008105-79-0
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: FTZSRGNLHPVEHB-UVTDQMKNSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  388.4±41.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (Z)-2-benzylidene-2,3-dihydrobenzofuran-3-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到aurone
  参考文献：
  名称：

  通过Au I催化的环化反应快速，多功能地合成金酮

  摘要：

  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。

  DOI：

  10.1021/jo702197b
• 作为产物：
  描述：

  2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol 在 苯乙烯 、 rhodium(II) pivalate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 (Z)-2-benzylidene-2,3-dihydrobenzofuran-3-ol
  参考文献：
  名称：

  双重催化：质子/金属催化串联苯并呋喃环化/碳转移反应

  摘要：

  已经开发了用于合成各种苯并呋喃基取代的环丙烷和环庚烯的有效的质子/金属催化的串联苯并呋喃环化/卡宾转移反应。建议该反应通过两个关键中间体进行，即邻醌甲基化物（o- QM）和苯并呋喃基卡宾。基于DFT的计算研究表明，反应物通过的脱水启动ø - HBA通过布朗斯台德酸介导的质子穿梭过渡状态，在形成关键中间体Ò -QM。

  DOI：

  10.1021/acs.orglett.6b00260

文献信息

• Copper-Catalyzed Dehydrative Cyclization of 1-(2-Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2-Phosphorylmethylbenzofurans
  作者：Ming Zhang、Jianlin Yang、Qing Xu、Chao Dong、Li-Biao Han、Ruwei Shen

  DOI：10.1002/adsc.201701368

  日期：2018.1.17

  A tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)PF6]‐catalyzed dehydrative reaction of 1‐(2‐hydroxyphenyl)propargyl alcohols with diarylphosphine oxides has been developed to provide an efficient synthesis of phosphorylated benzofurans in good to high yields. In the presence of a catalytic amount of an organic base, a variety of H‐phosphonates and H‐phosphinates can also be employed

  已开发了由四（乙腈）铜（I）六氟磷酸盐[Cu（MeCN）PF 6 ]催化的1-（2-羟苯基）炔丙醇与二芳基膦氧化物的脱水反应，以提供从高到高的磷酸化苯并呋喃的高效合成产量。在催化量的有机碱存在下，各种H-膦酸酯和H-次膦酸酯也可以用作良好的底物，以中等收率生产相应的产品。自从形成新的C（sp 3）-P键和苯并呋喃骨架都可以使用廉价的铜催化剂实现，而水是唯一的副产物。还证明了该产品的一些合成转化。
• One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst
  作者：Min Yu、Guangxiang Liu、Chengyan Han、Li Zhu、Xiaoquan Yao

  DOI：10.2174/1570178614666171110150853

  日期：2017.12.11

  Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation

  通过以联吡啶为配体的铜纳米粒子（Cu NPs）催化的2-（1-羟基丙-2-炔基）苯酚的氧化环化串联反应合成了金酮。在反应中，氧气起绿色和中度氧化剂的作用，以达到最佳效果。Cu NP被联吡啶配体和水双重激活，对氧的氧化和环化反应显示出高效的催化活性，从而生成金酮和类黄酮。
• 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.
• 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-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.