2-丙烯酸3-(3-氰基苯基)-丁酯 | 921212-90-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 2-丙烯酸3-(3-氰基苯基)-丁酯
• 英文名称: butyl 3-(3-cyanophenyl)acrylate
• 英文别名: Butyl 3-(3-cyanophenyl)prop-2-enoate
• CAS: 921212-90-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: KTRGOANMGFPEJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 3-氯苯腈 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以65%的产率得到2-丙烯酸3-(3-氰基苯基)-丁酯
  参考文献：
  名称：

  Palladium nanoparticles supported on modified crosslinked polyacrylamide containing phosphinite ligand: A novel and efficient heterogeneous catalyst for carbon–carbon cross-coupling reactions

  摘要：

  A novel palladium catalyst based on modified crosslinked polyacrylamide containing phosphinite ligand was synthesized and characterized. It exhibits excellent activity and stability in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions with different aryl halides including inactive aryl chlorides. Short reaction times with good to excellent yields of the desired products express the effectiveness of this catalyst in these reactions. Transmission electron microscopy (TEM) shows that palladium particles are well-dispersed and of typical diameter of 18-30 nm. The X-ray powder diffraction (XRD) pattern of the Pd catalyst is consistent with the metallic Pd(0). The turnover number (TON) of this catalyst reaches up to 9.5 x 10(4) for these C-C bond forming reactions. Elemental analysis of Pd by ICP-OES and hot filtration test shows low leaching of the metal into solution from the supported catalyst which confirms the full heterogeneous character of the catalytically active species. The catalyst can be used many times in repeating cycles without considerable loss in its activity. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.02.025

文献信息

• Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects
  作者：David Obermayer、Bernhard Gutmann、C. Oliver Kappe

  DOI：10.1002/anie.200904185

  日期：2009.10.19

  Running oil‐bath chemistry in a microwave! Using reaction vials made out of strongly microwave‐absorbing silicon carbide (SiC) in a microwave reactor simulates experiments conducted in an autoclave with conductive heating because of the efficient shielding of the electromagnetic field by the SiC vial. This technology makes it possible to study the significance of microwave effects.

  在微波炉中运行油浴化学反应！在微波反应器中使用由强烈吸收微波的碳化硅（SiC）制成的反应瓶，可以模拟在高压釜中进行传导加热的实验，因为SiC瓶可以有效屏蔽电磁场。这项技术使研究微波效应的重要性成为可能。
• Heterogeneous Versus Homogeneous Palladium Catalysts for Ligandless Mizoroki-Heck Reactions: A Comparison of Batch/Microwave and Continuous-Flow Processing
  作者：Toma N. Glasnov、Silvia Findenig、C. Oliver Kappe

  DOI：10.1002/chem.200802200

  日期：2009.1.12

  transformations in continuous‐flow mode. As a suitable ligandless catalyst system for the Mizoroki–Heck couplings both heterogeneous and homogeneous Pd catalysts (Pd/C and Pd acetate) were considered. In batch mode, full conversion with excellent selectivity for coupling was achieved applying high‐temperature microwave conditions with Pd levels as low as 10−3 mol %. In continuous‐flow mode with Pd/C as a catalyst

  研究了芳基碘化物和溴化物与丙烯酸丁酯的Mizoroki-Heck偶联作为模型系统，以连续流动模式进行过渡金属催化的转化。作为适用于Mizoroki-Heck偶联的无配体催化剂体系，非均相和均相Pd催化剂（Pd / C和乙酸Pd）均被考虑。在间歇模式下，在Pd含量低至10 -3的高温微波条件下，可实现具有出色耦合选择性的全转化 摩尔％。在以Pd / C为催化剂的连续流模式下，由于这些Mizoroki-Heck偶联通过涉及可溶性Pd胶体/纳米粒子的均相机理而进行，因此观察到了从非均相催化剂中大量Pd的浸出。通过使用低含量的乙酸钯作为均相钯预催化剂，在高温/高压流反应器中成功进行了连续流式Mizoroki-Heck转化。对于芳基碘化物和溴化物，都可以得到肉桂酸酯的高分离产物收率。讨论了涉及Pd催化的Mizoroki-Heck反应的机理问题。
• Continuous Flow Ligand-Free Heck Reactions Using Monolithic Pd [0] Nanoparticles
  作者：Nikzad Nikbin、Mark Ladlow、Steven V. Ley

  DOI：10.1021/op7000436

  日期：2007.5.1

  An automated reactor has been developed for performing ligand-free Heck reactions in continuous flow mode. The reactor utilises a monolithic reactor cartridge derivatised with Pd(0) nanoparticles in-line with a scavenging cartridge containing Quadrapure-TU to efficiently capture palladium residues and thereby afford Heck products directly in high purity.
• Ligand-Free Palladium Catalytic System Supported by CNT and its Application to the Mizoroki Heck Reactions
  作者：Young-Shin Jo、Ja-Young Kim、Il-Kwon Oh、Hyun-Chul Choi、Sun-Woo Lee

  DOI：10.5012/bkcs.2010.31.6.1735

  日期：2010.6.20
• Palladium nanoparticles supported on modified crosslinked polyacrylamide containing phosphinite ligand: A novel and efficient heterogeneous catalyst for carbon–carbon cross-coupling reactions
  作者：Bahman Tamami、Soheila Ghasemi

  DOI：10.1016/j.molcata.2010.02.025

  日期：2010.5.1

  A novel palladium catalyst based on modified crosslinked polyacrylamide containing phosphinite ligand was synthesized and characterized. It exhibits excellent activity and stability in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions with different aryl halides including inactive aryl chlorides. Short reaction times with good to excellent yields of the desired products express the effectiveness of this catalyst in these reactions. Transmission electron microscopy (TEM) shows that palladium particles are well-dispersed and of typical diameter of 18-30 nm. The X-ray powder diffraction (XRD) pattern of the Pd catalyst is consistent with the metallic Pd(0). The turnover number (TON) of this catalyst reaches up to 9.5 x 10(4) for these C-C bond forming reactions. Elemental analysis of Pd by ICP-OES and hot filtration test shows low leaching of the metal into solution from the supported catalyst which confirms the full heterogeneous character of the catalytically active species. The catalyst can be used many times in repeating cycles without considerable loss in its activity. (C) 2010 Elsevier B.V. All rights reserved.