4-(3-phenylpropioloyl)benzonitrile | 100752-58-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-(3-phenylpropioloyl)benzonitrile
• 英文别名: 1-(4-cyanophenyl)-3-phenylprop-2-yn-1-one；Benzonitrile, 4-(1-oxo-3-phenyl-2-propynyl)-；4-(3-phenylprop-2-ynoyl)benzonitrile
• CAS: 100752-58-7
• 化学式: C₁₆H₉NO
• 分子量: 231.254
• InChiKey: FPMZWZIBRYEEGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-phenylpropioloyl)benzonitrile 在 三(五氟苯基)硼烷 、 苯硅烷 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以50%的产率得到4-(3-phenylprop-2-ynyl)benzonitrile
  参考文献：
  名称：

  有机硼烷催化氢化物转移的炔酮选择性 1,2-还原：苄基炔烃的合成

  摘要：

  苄基炔烃是有机合成中重要的有机结构单元。我们在此报告 B(C 6 F 5 ) 3- 催化位点选择性 1,2- 还原现成的炔酮以获得苄基炔烃衍生物。在所开发的条件下，一系列炔酮底物以良好至优异的产率转化为相应的苄基炔烃产物。这种转化具有许多优点，包括不含过渡金属、反应条件温和、催化剂负载量低（5 mol%）、产率高（高达 99%）、底物范围广和官能团耐受性。此外，该方法的实用性通过仅一步操作即可将苄基炔烃产物多种转化为其他有用的化合物来证明。该协议为苄基炔烃的合成提供了一种方便的方法。

  DOI：

  10.1016/j.tetlet.2022.153645
• 作为产物：
  描述：

  对氰基苯甲酸 在 N-甲基吗啉 、 palladium diacetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.0h， 生成 4-(3-phenylpropioloyl)benzonitrile
  参考文献：
  名称：

  Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of “Super-Active Esters”

  摘要：

  A neat palladium-catalyzed alkynylation reaction was developed with "super-active ester" as the carbonyl electrophile, which provides a dean-and efficient synthetic protocol for a broad array Of ynone compounds under CO-, Cu-,, ligand-, and base-free conditions. The superior activity of triazine ester was rationalized by the strong electron;withdrawing ability and the unique affinity of triazine On palladium. A mechanistic experiment clearly demonstrated that the N-Pd coordination of triazine plays a crucial role for the highly efficient C-O activation.

  DOI：

  10.1021/acs.orglett.5b01466

文献信息

• Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
  作者：Mengting Meng、Guofang Wang、Liangfeng Yang、Kai Cheng、Chenze Qi

  DOI：10.1002/adsc.201701469

  日期：2018.3.20

  Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α‐keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones

  壬烷由于其多功能性而成为杂环衍生物的各种有机合成中的重要组成部分，而黄酮是具有广泛生物活性的重要一类天然产物。我们描述了芳基丙酸与α-酮酸的催化双脱羧炔基化反应。以Ag（I）/过硫酸盐为催化体系，可以容易地获得带有各种取代基的有价值的炔酮。邻位羟基取代基的引入α-酮酸的位点使该策略进一步适用于通过异环戊烷以类似的银催化体系以中等到良好的收率构建黄酮衍生物。反应在相对温和的反应条件下进行，并能耐受多种官能团。对照实验表明，两个反应均经历自由基过程。
• Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
  作者：Karoline T. Neumann、Simon R. Laursen、Anders T. Lindhardt、Benny Bang-Andersen、Troels Skrydstrup

  DOI：10.1021/ol5007289

  日期：2014.4.18

  A general procedure for the palladium-catalyzed carbonylative Sonogashira coupling of aryl bromides is reported, using near stoichiometric amounts of carbon monoxide. The method allows a broad substrate scope in moderate to excellent yields. The formed alkynone motive serves as a platform for synthesis of various heterocyclic structures, including pyrimidines. Furthermore, the presented strategy allows

  据报道，使用接近化学计量的一氧化碳，钯催化芳基溴化物的羰基化Sonogashira偶联反应的一般程序。该方法允许以中等至优异的产率在宽范围的基材上使用。形成的炔酮动机用作合成各种杂环结构（包括嘧啶）的平台。此外，提出的策略允许有效的13 C标记。
• Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1<i>H</i>-pyridines by Michael addition–cyclocondensation sequences
  作者：Natascha Breuer、Irina Gruber、Christoph Janiak、Thomas J J Müller

  DOI：10.3762/bjoc.15.262

  日期：——

  Starting from substituted alkynones, α-pyrones and/or 1H-pyridines were generated in a Michael addition–cyclocondensation with ethyl cyanoacetate. The peculiar product formation depends on the reaction conditions as well as on the electronic substitution pattern of the alkynone. While electron-donating groups furnish α-pyrones as main products, electron-withdrawing groups predominantly give the corresponding 1H-pyridines. Both heterocycle classes fluoresce in solution and in the solid state. In particular, dimethylamino-substituted α-pyrones, as donor–acceptor systems, display remarkable photophysical properties, such as strongly red-shifted absorption and emission maxima with daylight fluorescence and fluorescence quantum yields up to 99% in solution and around 11% in the solid state, as well as pronounced emission solvatochromism. Also a donor-substituted α-pyrone shows pronounced aggregation-induced emission enhancement.

  从取代炔酮出发，通过乙基氰乙酸酯的Michael加成-环缩合反应生成α-吡喃酮和/或1H-吡啶。独特的产物形成取决于反应条件以及炔酮的电子取代模式。虽然电子给予基团提供α-吡喃酮作为主要产物，但电子提取基团主要给出相应的1H-吡啶。这两类杂环在溶液和固态中均发出荧光。特别是二甲氨基取代的α-吡喃酮作为给体-受体系统，显示出显著的光物理性质，如强烈的红移吸收和发射最大值，具有日光荧光和溶液中高达99%的荧光量子产率，固态中约为11%，以及明显的发射溶剂致色变。此外，给体取代的α-吡喃酮显示出明显的聚集诱导发射增强。
• Synthesis of Trisubstituted Isoxazoles by Palladium(II)-Catalyzed Cascade Cyclization–Alkenylation of 2-Alkyn-1-one <i>O</i>-Methyl Oximes
  作者：Zhigang She、Dongyue Niu、Lei Chen、Maria A. Gunawan、Xhesika Shanja、William H. Hersh、Yu Chen

  DOI：10.1021/jo300090k

  日期：2012.4.6

  palladium-catalyzed, cascade 5-endo-dig cyclization–alkenylation synthesis of isoxazoles has been developed. The addition of 1 equiv of n-Bu4NBr significantly increases the yield of the desired 4-alkenyl-3,4,5-trisubstituted isoxazoles. A variety of trisubstituted isoxazoles are prepared in moderate to excellent yields. One example of the synthesis of a naphthoisoxazole is reported by a cascade cyclization–alkenylation-Heck

  已经开发了钯催化的异恶唑的级联5-内挖式环化-烯基化合成。加入1当量的n -Bu 4 NBr显着增加了所需的4-烯基-3,4,5-三取代异恶唑的产率。以中等至优异的产率制备了多种三取代的异恶唑。通过级联环化-烯基化-Heck反应报道了萘异恶唑合成的一个例子。
• Copper-Catalyzed CC Bond Formation through CH Functionalization: Synthesis of Multisubstituted Indoles from<i>N</i>-Aryl Enaminones
  作者：Roberta Bernini、Giancarlo Fabrizi、Alessio Sferrazza、Sandro Cacchi

  DOI：10.1002/anie.200902440

  日期：2009.10.12

  A variety of functionalities, including the whole range of halogen substituents, are tolerated in the title reaction, an intramolecular approach for the construction of a multisubstituted indole skeleton from readily available enaminones (see scheme; phen=1,10‐phenanthroline). The indole products are also prepared directly in high yield from α,β‐ynones and primary amines.

  标题反应具有多种功能，包括卤素取代基的整个范围，这是一种分子内方法，可从容易获得的烯胺酮中构建多取代的吲哚骨架（参见方案； phen = 1,10-phenothroline）。吲哚产物还可以直接由α，β-炔酮和伯胺直接制备得到。