4-(1-hept-1-ynyl)benzonitrile | 64146-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(1-hept-1-ynyl)benzonitrile
• 英文别名: 4-(1-heptynyl)benzonitrile；1-p-Cyanphenyl-1-heptyn；4-Hept-1-ynylbenzonitrile
• CAS: 64146-59-4
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: PEUYCIGQJDMKOG-UHFFFAOYSA-N

物化性质

• 沸点：
  325.0±25.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.8
• 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 4-(1-hept-1-ynyl)benzonitrile
  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

• A copper-free Sonogashira reaction using nickel ferrite as catalyst in water
  作者：Firouz Matloubi Moghaddam、Ghazal Tavakoli、Hamid Reza Rezvani

  DOI：10.1016/j.catcom.2014.11.018

  日期：2015.2

  The Sonogashira reaction using nickel ferrite nanoparticles as catalyst and under copper-free conditions was investigated in water as a green solvent. Various types of aryl and alkyl halides were successfully coupled with phenyl acetylene under the optimized reaction conditions with very good to excellent yields at a short time. The catalyst is easily recoverable and can be reused for several runs

  以水为绿色溶剂，研究了使用镍铁氧体纳米粒子作为催化剂并在无铜条件下进行的Sonogashira反应。在优化的反应条件下，各种类型的芳基卤化物和烷基卤化物成功地与苯基乙炔偶联，并且在短时间内具有非常好至极好的收率。该催化剂易于回收，并且可以以良好的周转率重复使用数次。
• Versatile palladium-catalyzed arylation of organomanganese chlorides by aryl bromides
  作者：Eric Riguet、Mouâd Alami、Gérard Cahiez

  DOI：10.1016/s0022-328x(00)00891-3

  日期：2001.4

  In THF, a palladium-catalyzed cross-coupling reaction of organomanganese reagents with various aryl bromides including unreactive deactivated or hindered aryl bromides was performed successfully in the presence of a new catalytic system 1% PdCl2(dppp)-four equivalents DME. The scope of the reaction is very broad since many functional groups are tolerated, moreover, even hindered O,O ' -di- or trisubstituted diaryls were obtained in E;igh yields. It is interesting to note that hindered aryl bromides are more reactive than the corresponding aryl iodides. Alkyl, alkenyl and alkynylmanganese chlorides also react under similar conditions. (C) 2001 Elsevier Science B.V. All rights reserved.
• Rates and regioselectivities of the palladium-catalyzed ethynylation of substituted bromo- and dibromobenzenes
  作者：Rina Singh、George Just

  DOI：10.1021/jo00279a040

  日期：1989.9
• A general synthesis of terminal and internal arylalkynes by the palladium-catalyzed reaction of alkynylzinc reagents with aryl halides
  作者：Anthony O. King、Eiichi Negishi、Frank J. Villani、Augustine Silveira

  DOI：10.1021/jo00396a046

  日期：1978.1
• Cross-Coupling of Alkynylsilanols with Aryl Halides Promoted by Potassium Trimethylsilanolate
  作者：Scott E. Denmark、Steven A. Tymonko

  DOI：10.1021/jo0351771

  日期：2003.11.1

  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.