1-[4-(1-heptynyl)phenyl]ethanone | 627885-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(1-heptynyl)phenyl]ethanone
• 英文别名: 4-(hept-1-ynyl)acetophenone；1-[4-(hept-1-ynyl)phenyl]ethanone；4-(1-heptynyl)acetophenone；1-(4-acetylphenyl)-1-heptyne；Ethanone, 1-[4-(1-heptynyl)phenyl]-；1-(4-hept-1-ynylphenyl)ethanone
• CAS: 627885-32-9
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: AQNVIORUKQGPCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  336.5±25.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-heptynyldimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 potassium trimethylsilonate 、 水 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 3.17h， 生成 1-[4-(1-heptynyl)phenyl]ethanone
  参考文献：
  名称：

  Cross-Coupling of Alkynylsilanols with Aryl Halides Promoted by Potassium Trimethylsilanolate

  摘要：

  The palladium-catalyzed cross-coupling of aliphatic alkynylsilanols with aryl iodides has been demonstrated with potassium trimethylsilanolate as the coupling promoter and copper(I) iodide as a cocatalyst. The cross-coupling proceeds at room temperature in good to excellent yield with a range of aryl iodides. A comparison of the reactivity of alkynylsilanols, trimethylsilylalkynes, and terminal alkynes under fluoride and fluoride-free conditions was per-formed to elucidate the role of silicon in the Sonogashira reaction.

  DOI：

  10.1021/jo0351771

文献信息

• Palladium-Catalyzed Decarboxylative<i>sp</i>-<i>sp</i>²Cross-Coupling Reactions of Aryl and Vinyl Halides and Triflates with α,β-Ynoic Acids using Silver Oxide
  作者：Hyunseok Kim、Phil Ho Lee

  DOI：10.1002/adsc.200900502

  日期：2009.11

  Palladium-catalyzed decarboxylative sp-sp2 cross-coupling reactions of aryl and vinyl halides and triflates with α,β-ynoic acids using silver oxide have been developed. A variety of α,β-ynoic acids were readily decarboxylated in the presence of silver oxide and then, generated in situ, silver acetylides were coupled with electrophiles in the presence of a palladium(0) catalyst under neutral conditions

  已经开发了使用氧化银的芳族卤化物和乙烯基卤化物以及三氟甲磺酸与钯，α-炔酸的钯催化的脱羧sp-sp 2交叉偶联反应。多种α，β炔酸在氧化银的存在下，容易地脱羧，然后，生成的原位，银乙炔化物加上在中性条件下在钯（0）催化剂的存在下亲电子，产生对称或不对称的二芳基乙炔，芳基烷基乙炔和芳基乙烯基乙炔，收率良好至优异。
• Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides
  作者：Jeongju Moon、Mihee Jang、Sunwoo Lee

  DOI：10.1021/jo802290r

  日期：2009.2.6

  2-Octynoic acid and phenylpropiolic acid were employed for the palladium-catalyzed decarboxylative coupling reaction and with a variety of aryl halides. The former needed 1,4-bis(diphenylphosphino)butane (dppb) as a ligand and the latter tri-tert-butylphosphine (PtBu3), and both required 2 equiv of tetra-n-butylammonium fluoride (TBAF) for full conversion. These reactions showed high reactivities and

  2-辛酸和苯丙酸用于钯催化的脱羧偶联反应以及各种芳基卤化物。前者需要1,4-双（二苯基膦基）丁烷（DPPB）作为配体，而后者三-叔丁基膦（P吨卜3），并且两个需要2当量的四- ñ全丁基氟化铵（TBAF）转换。这些反应显示出高反应性和对官能团如乙烯基，酯，醚，酮和胺的耐受性。
• Sonogashira Cross-Coupling Using Carbon Aerogel Doped with Palladium Nanoparticles; A Recoverable and Reusable Catalyst
  作者：Sandro Cacchi、Adelina Vallribera、Roger Soler、Giancarlo Fabrizi、Giovanni Forte、Laura Martín、Sandra Martínez、Elies Molins、Marcial Moreno-Mañas、Francesco Petrucci、Anna Roig、Rosa Sebastián

  DOI：10.1055/s-2007-983888

  日期：2007.10

  The Sonogashira cross coupling of aryl iodides with terminal alkynes has been carried out in the presence of carbon aerogels doped with metallic palladium nanoparticles. Coupling products have been isolated in excellent yields and the catalyst system can be easily recovered in the presence of air without any particular precautions and reused several times.

  在掺杂金属钯纳米粒子的碳气凝胶存在下，进行了芳基碘与末端炔烃的Sonogashira交叉偶联反应。偶联产物以优异的产率被分离出来，催化体系可以在空气中轻松回收，无需特别预防措施，并可多次重复使用。
• CuI/PPh₃/PEG–Water: An Efficient Catalytic System for Cross-Coupling Reaction of Aryl Iodides and Alkynes
  作者：Gong Chen、Jianwei Xie、Jiang Weng、Xinhai Zhu、Zhanchao Zheng、Jiwen Cai、Yiqian Wan

  DOI：10.1080/00397911.2010.517363

  日期：2011.11.1

  Abstract An efficient protocol for the copper-catalyzed Sonogashira coupling of aryl iodides with terminal acetylenes in water–polyethylene glycol has been established. Both electron-rich and electron-deficient aryl iodides were arylalkynated under microwave heating or reflux in oil bath to afford good to excellent yields.

  摘要 建立了一种在水-聚乙二醇中铜催化芳基碘与末端乙炔的 Sonogashira 偶联的有效方案。在微波加热或油浴回流下，富电子和缺电子芳基碘化物均被芳基炔化，以提供良好至极好的产率。
• Sonogashira Cross-Coupling of Arenediazonium Salts
  作者：Giancarlo Fabrizi、Antonella Goggiamani、Alessio Sferrazza、Sandro Cacchi

  DOI：10.1002/anie.201000472

  日期：2010.6.1

  Star‐crossed lovers: The domino iododediazoniation/Sonogashira cross‐coupling of terminal alkynes with arenediazonium salts has been developed. The arenediazonium salt synthesis/iododediazoniation/Sonogashira cross‐coupling sequence can also be performed as a one‐pot process, omitting the isolation of the arenediazonium salt.

  跨星恋人：已开发出末端炔烃与槟榔重氮盐的多米诺胺碘去重氮/ Sonogashira交叉偶联。槟榔碱盐的合成/碘去重氮离子化/ Sonogashira交叉偶联序列也可以作为一锅法进行，省去了槟榔碱盐的分离。