(Z)-(1-phenoxyethene-1,2-diyl)dibenzene | 1219621-30-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-(1-phenoxyethene-1,2-diyl)dibenzene
• 英文别名: [(Z)-1,2-diphenylethenoxy]benzene
• CAS: 1219621-30-3
• 化学式: C₂₀H₁₆O
• 分子量: 272.346
• InChiKey: ZFWCGZNIXVNQCH-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯基乙炔 、 苯酚 在 zinc(II) acetylacetonate 、 C₂₆H₂₂AuClN₄ 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以97%的产率得到(Z)-(1-phenoxyethene-1,2-diyl)dibenzene
  参考文献：
  名称：

  具有卡宾-联吡啶配体的杂双金属催化支架的构建：金-锌双金属催化 O-亲核试剂与非活化炔烃的分子间加成

  摘要：

  制备了在 C5 位具有 2,2'-联吡啶部分的咪唑并[1,5 - a ]吡啶-3-亚基配体的金 (I) 配合物作为构建异质双金属协同催化剂的模板。原位生成的金-锌双金属体系使O亲核试剂（如羧酸和酚类）向未活化的内部炔烃发生分子间亲核反加成。DFT 计算支持提出的阳离子金原子和锌盐位点分别用于活化炔烃和羧酸的协同作用。

  DOI：

  10.1021/acscatal.2c01701

文献信息

• Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes
  作者：Marcia E Richard、Daniel V Fraccica、Kevin J Garcia、Erica J Miller、Rosa M Ciccarelli、Erin C Holahan、Victoria L Resh、Aakash Shah、Peter M Findeis、Robert A Stockland Jr.

  DOI：10.3762/bjoc.9.235

  日期：——

  A range of arylgold compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos or IPr/SIPr. Phenols bearing either electron-withdrawing or electron-donating groups were efficiently added using these catalysts. No silver salts, acids, or solvents were needed for the catalysis, and either microwave or conventional heating afforded moderate to excellent yields of the vinyl ethers.

  一系列芳基金属化合物已被合成并作为单组分催化剂用于未活化内部炔烃的水杂氧化反应。在这项工作中，对含有卡宾和膦配体的化合物进行了筛选，效率最高的催化剂包括JohnPhos或IPr/SIPr。使用这些催化剂可以高效地添加带有电子吸引或电子给予基团的酚。对乙烯醚的产率中等至优良，无需银盐、酸或溶剂进行催化，可以采用微波或传统加热。
• Gold-Catalyzed Intermolecular Hydrophenoxylation of Unactivated Internal Alkynes
  作者：Malleswara Rao Kuram、M. Bhanuchandra、Akhila K. Sahoo

  DOI：10.1021/jo1000143

  日期：2010.4.2

  A general and simple strategy for the synthesis of functionally diverse arylvinyl ethers is reported through gold-catalyzed intermolecular addition of electronically and sterically substituted phenols with unactivated alkynes. Addition of phenols to unsymmetrical alkynes provides the corresponding mixture of regioisomers with appreciable selectivity. Multiple hydrophenoxylations of polyphenols with

  通过金催化的电子和空间取代的苯酚与未活化炔烃的分子间加成反应，已报道了合成功能多样的芳基乙烯基醚的一般和简单策略。将苯酚添加到不对称炔烃中可提供相应的区域异构体混合物，并具有明显的选择性。成功地证明了多酚与二苯乙炔的多次加氢苯氧基化。
• Hydrophenoxylation of Alkynes by Cooperative Gold Catalysis
  作者：Yoshihiro Oonishi、Adrián Gómez-Suárez、Anthony R. Martin、Steven P. Nolan

  DOI：10.1002/anie.201304182

  日期：2013.9.9

  Double impact: The title method gives aryl vinyl ethers in high yields, short reaction times, Z‐stereospecificity, and good regioselectivities. Insights into the reaction mechanism highlight the role of [Au(NHC)}2(μ‐OH)][BF4] (NHC=N‐heterocyclic carbene) as both a Lewis acid, [Au(NHC)][BF4], and a Brønsted base, [Au(NHC)(OH)], thereby generating a synergistic effect between the two gold moieties.

  双重影响：标题方法可提供高收率，较短的反应时间，Z-立体特异性和良好的区域选择性的芳基乙烯基醚。对反应机理的洞察力突出了[Au（NHC）} 2（μ-OH）] [BF 4 ]（NHC = N-杂环卡宾）作为路易斯酸[Au（NHC）] [BF 4 ]和布朗斯台德碱[Au（NHC）（OH）]，从而在两个金基团之间产生协同效应。
• Hydrophenoxylation of internal alkynes catalysed with a heterobimetallic Cu-NHC/Au-NHC system
  作者：Faïma Lazreg、Stefano Guidone、Alberto Gómez-Herrera、Fady Nahra、Catherine S. J. Cazin

  DOI：10.1039/c6dt04513h

  日期：——

  A dual catalytic process based on a heterobimetallic system, consisting of Cu-NHC and Au-NHC complexes, was shown to be highly active and selective for the hydrophenoxylation of internal alkynes.

  基于铜-NHC和金-NHC配合物的异双金属体系的双催化过程被证明对内部炔烃的水杂苯氧基化具有高活性和选择性。
• Construction of Heterobimetallic Catalytic Scaffold with a Carbene-Bipyridine Ligand: Gold–Zinc Two-Metal Catalysis for Intermolecular Addition of <i>O</i>-Nucleophiles to Nonactivated Alkynes
  作者：Vishal Kumar Rawat、Kosuke Higashida、Masaya Sawamura

  DOI：10.1021/acscatal.2c01701

  日期：2022.7.15

  A gold(I) complex bearing an imidazo[1,5-a]pyridin-3-ylidene ligand with a 2,2′-bipyridine moiety at the C5 position was prepared as a template for constructing heterobimetallic cooperative catalysts. In situ generated gold–zinc bimetallic systems enabled intermolecular nucleophilic anti-addition of O-nucleophiles such as carboxylic acids and phenols toward nonactivated internal alkynes. DFT calculations

  制备了在 C5 位具有 2,2'-联吡啶部分的咪唑并[1,5 - a ]吡啶-3-亚基配体的金 (I) 配合物作为构建异质双金属协同催化剂的模板。原位生成的金-锌双金属体系使O亲核试剂（如羧酸和酚类）向未活化的内部炔烃发生分子间亲核反加成。DFT 计算支持提出的阳离子金原子和锌盐位点分别用于活化炔烃和羧酸的协同作用。