ethyl (Z)-2-(4-methoxyphenyl)-3-phenylacrylate | 688773-63-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl (Z)-2-(4-methoxyphenyl)-3-phenylacrylate
• 英文别名: ethyl (Z)-2-(4-methoxyphenyl)-3-phenyl-2-propenoate；ethyl (Z)-2-(4-methoxyphenyl)-3-phenylprop-2-enoate
• CAS: 688773-63-9
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: DOVJOGGNLKELAC-LGMDPLHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙炔酸乙酯 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 12.0h， 生成 ethyl (Z)-2-(4-methoxyphenyl)-3-phenylacrylate
  参考文献：
  名称：

  Novel Stereoselective Synthesis of (Z)-α,β-Unsaturated Esters by Hydrostannylation-Stille Tandem Reaction of Alkynyl Esters with Aryl Iodides

  摘要：

  (Z)-α,β-不饱和酯可以在温和的条件下，通过炔基酯的氢化锡化反应，然后与芳基碘化物发生 Stille 交叉偶联反应，在一锅内立体选择性地合成，而且产量很高。

  DOI：

  10.3184/174751911x13192956847054

文献信息

• Novel Stereoselective Synthesis of (<i>Z</i>)-α,β-Unsaturated Esters by Hydrostannylation-Stille Tandem Reaction of Alkynyl Esters with Aryl Iodides
  作者：Jianying Li、Yan Yu、Mingzhu Cheng、Mingzhong Cai

  DOI：10.3184/174751911x13192956847054

  日期：2011.11

  ( Z)-α,β-Unsaturated esters can be stereoselectively synthesised in one pot under mild conditions and in good yields, by the hydrostannylation of alkynyl esters followed by Stille cross-coupling with aryl iodides.

  (Z)-α,β-不饱和酯可以在温和的条件下，通过炔基酯的氢化锡化反应，然后与芳基碘化物发生 Stille 交叉偶联反应，在一锅内立体选择性地合成，而且产量很高。
• Rhodium(I)-Catalyzed Defluorinative Coupling of Boronic Acids with Monofluoroalkenes
  作者：Yuwei Zong、Yihan Tang、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.2c02294

  日期：2022.9.9

  We herein describe a highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-β-monofluoroacrylates. In contrast to previous methods, the trisubstituted (Z)-alkene products were obtained in excellent dr with an inversion of double bond geometry. Experimental and computational studies established that Rh(I)-facilitated β-F elimination is favored over competing β-H elimination

  我们在此描述了硼酸与 ( E )-β-单氟丙烯酸酯的高选择性 Rh(I) 催化的脱氟偶联。与以前的方法相比，三取代的 ( Z )-烯烃产物以优异的 dr 获得，双键几何形状反转。实验和计算研究表明，Rh(I) 促进的 β-F 消除优于竞争性 β-H 消除和原脱金属。
• Palladium-Catalyzed Hydroarylation of Alkynes with Arenediazonium Salts
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Daniela Persiani

  DOI：10.1021/ol800266e

  日期：2008.4.1

  The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (2)-2-arylcinnamates stereo- and regioselectively.
• Palladium-Catalyzed Regio- and Stereoselective Hydrosilylation of Electron-Deficient Alkynes
  作者：Yuto Sumida、Tomoe Kato、Suguru Yoshida、Takamitsu Hosoya

  DOI：10.1021/ol300279c

  日期：2012.3.16

  Highly regio- and stereoselective hydrosilylation applicable to a broad range of electron-deficient alkynes has been established using palladium catalysis. The synthetic utility of the method has been demonstrated by further transformations of α-silylalkenes, particularly Hiyama coupling and stereoinverting iododesilylation followed by Suzuki–Miyaura coupling, which enables stereodivergent syntheses

  使用钯催化已经建立了适用于多种缺电子炔烃的高度区域选择性和立体选择性氢化硅烷化。该方法的合成效用已通过α-甲硅烷基烯烃的进一步转化，特别是Hiyama偶联和碘代甲硅烷基化的立体转化，再加上Suzuki-Miyaura偶联得以证明，这使得α-芳烯酸酯能够立体发散。