3-(3-nitrophenyl)-1-phenylprop-2-yn-1-one | 129972-90-3

• 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: 3-(3-nitrophenyl)-1-phenylprop-2-yn-1-one
• 英文别名: 3-(3-nitrophenyl)-1-phenylpropynone；3-(3-Nitrophenyl)-1-phenyl-2-propyn-1-one
• CAS: 129972-90-3
• 化学式: C₁₅H₉NO₃
• 分子量: 251.241
• InChiKey: PPFBVVKWYQVYKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-nitrophenyl)-1-phenylprop-2-yn-1-one 在 氢氧化钾 、 水 作用下， 以 乙醚 为溶剂， 以80%的产率得到3-硝基苯乙炔
  参考文献：
  名称：

  A method for the preparation of terminal acetylenes

  摘要：

  A new pathway is proposed for the preparation of terminal acetylenes entailing the condensation of acid chlorides with phenylacetylene, isomerization of the acetylenic ketones with displacement of the oxo group and triple bond in the ketoacetylenic fragment, and subsequent alkaline cleavage of the isomerized ketones.

  DOI：

  10.1007/bf00958856
• 作为产物：
  描述：

  间硝基苯甲酰氯 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 三乙胺 、 copper(l) chloride 、 三氯氧磷 作用下， 以 甲苯 、 苯 为溶剂， 反应 8.0h， 生成 3-(3-nitrophenyl)-1-phenylprop-2-yn-1-one
  参考文献：
  名称：

  Isomerization of ?-acetylenic ketones

  摘要：

  A method is suggested for isomerization of alpha-acetylenic ketones with migration of the oxo group from position 1 to position 3 and of the triple bond from position 2 to position 1 of the ketoacetylenic fragment; it consists of addition of Et2NH at the triple bond of the ketone, conversion of the adduct to the imminium salt with POCl3, followed by alkaline hydrolysis. The isomerization is achieved in one preparative stage without isolation of intermediate compounds.

  DOI：

  10.1007/bf00958259

文献信息

• Palladium-Catalyzed Cross-Coupling of Electron-Poor Terminal Alkynes with Arylboronic Acids under Ligand-Free and Aerobic Conditions
  作者：Ming-Bo Zhou、Wen-Ting Wei、Ye-Xiang Xie、Yong Lei、Jin-Heng Li

  DOI：10.1021/jo101063p

  日期：2010.8.20

  Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)2 and Ag2O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding internal alkynes in moderate to good yields. Moreover, this methodology was applied to the synthesis

  已经描述了末端炔与芳基硼酸的钯催化的交叉偶联反应。在Pd（OAc）2和Ag 2 O的存在下，包括电子贫乏的末端炔在内的各种末端炔与许多硼酸的反应顺利进行，从而以中等至良好的收率提供了相应的内部炔。而且，该方法学被用于1 H-异苯并二酮和二炔的合成。值得注意的是，反应在无配体和相对较低的负载Pd条件下进行，反应的最大TON（转化数）高达720,000。
• One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling–intramolecular cyclization
  作者：Narasimha Swamy Thirukovela、Ramesh Balaboina、Vinayak Botla、Ravinder Vadde、Sreekantha Babu Jonnalagadda、Chandra Sekhar Vasam

  DOI：10.1039/c9cy01335k

  日期：——

  Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone–amine cyclization under PTC conditions was described. The results of controlled

  在环境友好的PEG-400 / H 2中原位生成的Pd-纳米颗粒（PdNPs）在区域选择性一锅合成3,5-di和3,4,5-三取代的吡唑和3,5-二取代的异恶唑的催化剂效力描述了一种O介质，它涉及（i）在PTC条件下无Cu的酰基-Sonogashira偶联（ASC）和（ii）分子内的ynone-amine环化。受控实验的结果支持两个连续的催化循环（ASC /环化）的操作，并通过一锅法通过与炔酮结合的钯实现互补/相反的区域选择性。而且，就地一锅法反应序列的第一个催化循环后回收的PdNPs已连续五次再次使用。此外，在进行上述研究之前，某些常见的Pd-N-杂环卡宾（Pd-NHC）配合物在水和有机物中催化相同的一锅两步反应顺序（无铜ASC /环化）的功效还优化了溶剂。还可以从水中的Pd-NHC上方原位生成PdNP，但由于它们的尺寸较大，因此无法重复使用。
• Chemistry of 1,3-diarylpropynones in superacids
  作者：A. V. Vasilyev、S. Walspurger、M. Haouas、J. Sommer、P. Pale、A. P. Rudenko

  DOI：10.1039/b412323a

  日期：——

  In superacids with H0 = −14 to −20, it has been found that 1,3-diarylpropynones ArCCCOAr′ are either protonated on oxygen of carbonyl groups with the formation of stable ions ArCCC(O+H)Ar′ or undergo further transformations when the highly conjugated system is electron-rich enough. In the latter case, 3-arylindenones are produced very rapidly and with high efficiency (up to 95% yield in less than 30 min). The influence of the substituents Ar, Ar′ and of the reaction conditions on the behavior of 1,3-diarylpropynones and on the intramolecular cyclisation have been studied. From the collected data, a mechanism has been proposed involving vinyl cations ArC+=CHCOAr′ and/or dications ArC+=CHC(O+H)Ar′.

  在pH值为−14至−20的超酸中，发现1,3-二芳基丙炔酮ArCCCOAr′可以通过羰基氧的质子化形成稳定的离子ArCCC(O+H)Ar′，或者当高度共轭体系的电子丰富时发生进一步转化。在后者的情况下，3-芳基茚酮非常迅速且高效地生成（在不到30分钟内产率可达95%）。对取代基Ar、Ar′和反应条件对1,3-二芳基丙炔酮行为以及分子内环化的影响进行了研究。根据收集的数据，提出了一种机制，涉及乙烯基阳离子ArC+=CHCOAr′和/或二阳离子ArC+=CHC(O+H)Ar′。
• (Benzoyliodomethyl)triphenylphosphonium Iodide: A Convenient Reagent for Direct Synthesis of Arylethynyl Phenyl Ketones by Chain Extension of Aldehydes
  作者：Manoutcher Iman、Pascal Bouyssou、Jacques Chenault

  DOI：10.1055/s-1990-26964

  日期：——

  Reaction between (benzoyliodomethyl)triphenylphosphonium iodide, potassium carbonate and various aromatic aldehydes in a liquid-solid two-phase system, gives arylethynyl phenyl ketones in good yield.

  在液固两相体系中，(苯甲酰碘甲基)三苯基碘化鏻、碳酸钾和各种芳香醛发生反应，生成芳炔基苯基酮，收率很高。
• SHVARTSBERG, M. S.;FEDENOK, L. G., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2094-2098
  作者：SHVARTSBERG, M. S.、FEDENOK, L. G.

  DOI：——

  日期：——