3-phenyl-1-(2-(2-phenylethynyl)phenyl)prop-2-yn-1-one | 43074-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-phenyl-1-(2-(2-phenylethynyl)phenyl)prop-2-yn-1-one
• 英文别名: 3-Phenyl-1-[2-(2-phenylethynyl)phenyl]prop-2-yn-1-one；3-phenyl-1-[2-(2-phenylethynyl)phenyl]prop-2-yn-1-one
• CAS: 43074-42-6
• 化学式: C₂₃H₁₄O
• 分子量: 306.364
• InChiKey: VYSYIDIITCKJAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(2-(2-phenylethynyl)phenyl)prop-2-yn-1-one 在 三苯基膦氯金 、 水 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.8h， 以75%的产率得到(4-hydroxy-2-phenylnaphthalen-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Gold-Catalyzed Hydrative Carbocyclization of 1,5- and 1,6-Diyn-3-ones via an Oxygen Transfer Process

  摘要：

  This study reports new hydrative carbocyclizations of 1,5- and 1,6-diyn-3-ones catalyzed by PPh3AuOTf, involving a pi-alkyne-assisted oxygen transfer in the reaction mechanisms. Treatment of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes with PPh3AuOTf (5 mol %) in wet 1,4-dioxane (23 degrees C, 10 min) led to hydrative aromatization to give 4-hydroxyl-1-naphthyl ketones efficiently. This approach is also extendible to the hydrative cyclization of acyclic 1,5-diyn-3-ones, which afforded 4-cyclopentenonyl ketones in reasonable yields. On the basis of this oxygen-labeling study, we propose a plausible mechanism involving an alkyne-assisted oxygen transfer to generate key oxonium and gold-enolate intermediates.

  DOI：

  10.1021/jo801753g
• 作为产物：
  描述：

  2-苯基乙炔基苯甲醛 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 16.17h， 生成 3-phenyl-1-(2-(2-phenylethynyl)phenyl)prop-2-yn-1-one
  参考文献：
  名称：

  银（I）催化的新型级联环化反应：将异戊烯并入异戊二烯。

  摘要：

  炔酮与醇的银（I）催化反应代表了合成1-烯基异色酮的通用工具。该反应最有可能通过形成苯并吡啶阳离子来进行，该苯并吡啶阳离子随后经受醇的亲核攻击以得到环合产物。

  DOI：

  10.1021/jo051524q

文献信息

• Brønsted/Lewis Acid-Promoted Site-Selective Intramolecular Cycloisomerizations of Aryl-Fused 1,6-Diyn-3-ones for Diversity-Oriented Synthesis of Benzo-Fused Fluorenes and Fluorenones and Naphthyl Ketones
  作者：Mou Mandal、Shanmugam Sakthivel、Rengarajan Balamurugan

  DOI：10.1021/acs.joc.0c02131

  日期：2021.1.1

  intramolecular cyclization of aryl-fused 1,6-diyn-3-ones. Synthesis of benzo[a]fluorenes and naphthyl ketones has been achieved selectively using TfOH and AgBF4, respectively, via in situ-formed acetals. Aryl-fused 1,6-diyn-3-ones undergo triflic acid-mediated intramolecular cyclization, leading to benzo[b]fluorenone derivatives via a radical intermediate as supported by EPR studies. Kinetic studies

  本文中，通过芳基稠合的1，6-二炔-3-酮的位点选择性分子内环化，已经证明了一种容易的以多样性为导向的方法来接近官能化的苯并[ a ]芴，苯并[ b ]芴酮和萘基酮。分别使用TfOH和AgBF 4分别通过原位形成的缩醛选择性地完成了苯并[ a ]芴和萘基酮的合成。芳基稠合的1,6-二炔-3-酮经历三氟甲磺酸-介导的分子内环化，从而导致苯并[ b ]芴酮衍生物通过EPR研究支持的基本中间体。还通过紫外可见光谱分析对这些转变进行了动力学研究，以阐明反应概况。
• Sequential [3+2] Cycloaddition/Air Oxidation Reactions: Triazoloyl Ion Assisted Oxidative Cleavage of Alkynes
  作者：Thanasekaran Ponpandian、Shanmugam Muthusubramanian、Sridharan Rajagopal

  DOI：10.1002/ejoc.201300441

  日期：2013.7

  Upon treatment with sodium azide in DMF, bisalkynes undergo chemoselective [3+2] cycloaddition followed by oxidative cleavage of the other alkyne unit by atmospheric oxygen. The neighboring triazoloyl ion is found to assist the cleavage process ultimately to deliver an acid and an aldehyde.

  在 DMF 中用叠氮化钠处理后，双炔烃发生化学选择性 [3+2] 环加成反应，然后被大气氧氧化裂解另一个炔烃单元。发现相邻的三唑酰基离子有助于裂解过程，最终传递酸和醛。
• <i>N</i>-Iodosuccinimide-Promoted Rapid Access to Indeno[1,2-<i>c</i>]pyrroles<i>via</i>[3+2] Annulation of Enamine-alkynes
  作者：Jampani Santhi、Beeraiah Baire

  DOI：10.1002/adsc.201600711

  日期：2016.12.7

  (NIS)‐promoted, cascade strategy for the efficient synthesis of biologically important indeno[1,2‐c]pyrroles via a [3+2] annulation process of enamine‐alkynes. This methodology had shown a very broad scope for diversely functionalized enamines and alkynes. We have also developed a one‐pot, multicomponent strategy for the direct synthesis of indeno‐pyrroles from diynones via enamine‐alkynes. Control experiments

  我们已经开发了一种无金属，N-碘代琥珀酰亚胺（NIS）促进的级联策略，用于通过烯胺炔烃的[3 + 2]环合法有效合成重要的生物学上重要的茚并[1,2- c ]吡咯。该方法学显示了功能多样的烯胺和炔烃的广泛应用范围。我们还开发了一种单锅多组分策略，可通过烯胺炔烃直接从二酮中合成茚并吡咯。对照实验支持NIS通过离子机制而非自由基途径作为亲电子活化剂的参与。
• Gold-catalyzed cyclization of 1,6-diynyl dithioacetals via 1,7-carbene transfer and aromatic C–H functionalization
  作者：Wei Xu、Ming Chen、Ning Sun、Yuanhong Liu

  DOI：10.1039/c6cc05302e

  日期：——

  A gold-catalyzed cyclization of 1,6-diynyl dithioacetals has been developed, which provides an attractive route to diverse-substituted benzo[a]fluorene derivatives. The reaction is initiated through 1,2-sulfur migration of propargyl dithioacetal moiety to...

  已经开发了金催化的1，6-二炔基二硫缩醛的环化，这为各种取代的苯并[a]芴衍生物提供了诱人的途径。该反应是通过炔丙基二硫缩醛部分的1,2-硫迁移至...
• Intramolecular [4 + 2] Cycloaddition Reactions of Diarylacetylenes:  Synthesis of Benzo[<i>b</i>]fluorene Derivatives via Cyclic Allenes
  作者：David Rodríguez、Armando Navarro、Luis Castedo、Domingo Domínguez、Carlos Saá

  DOI：10.1021/ol991391t

  日期：2000.6.1

  intramolecular [4 + 2] cycloaddition to give benzo[b]fluorene derivatives in good yields. The hybridization of the tether connecting the reacting alkynes has a pronounced effect on the course of the reaction. Theoretical calculations and isotopic labeling studies support a mechanism which involves the generation of a cyclic allene intermediate that evolves to the final benzo[b]fluorene.

  2-丙烯基二芳基乙炔经过分子内[4 + 2]热环加成反应，以高收率得到苯并[b]芴衍生物。连接反应的炔烃的系链的杂交对反应过程具有显着影响。理论计算和同位素标记研究支持了一种机制，该机制涉及生成环状丙二烯中间体，该中间体发展为最终的苯并[b]芴。