ethyl (E)-3-(4-vinylphenyl)acrylate | 1174761-22-8

• 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
• 英文名称: ethyl (E)-3-(4-vinylphenyl)acrylate
• 英文别名: (E)-ethyl 3-(4-vinylphenyl)acrylate；ethyl (2E)-3-(p-vinylphenyl)prop-2-enoate；ethyl (E)-3-(4-ethenylphenyl)prop-2-enoate
• CAS: 1174761-22-8
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: YCIREPNGPQKUAQ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(4-vinylphenyl)acrylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 生成 (E)-3-(4-vinylphenyl)prop-2-en-1-ol
  参考文献：
  名称：

  烯丙醇的催化对映选择性二溴化

  摘要：

  已经开发了一种新的二溴化反应，涉及将二溴丙二酸作为溴源和溴化钛物种作为溴源的组合。酒石酸衍生的二醇通过明显的配体加速实现了对映选择性催化。

  DOI：

  10.1021/ja4083182
• 作为产物：
  描述：

  对溴苯甲醛 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 mineral oil 为溶剂， 反应 28.0h， 生成 ethyl (E)-3-(4-vinylphenyl)acrylate
  参考文献：
  名称：

  Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres

  摘要：

  A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-Toll as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include alpha-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.

  DOI：

  10.1021/acs.orglett.8b03794

文献信息

• Ruthenium-Catalyzed, One-Pot Alcohol Oxidation-Wittig Reaction Producing α,β-Unsaturated Esters
  作者：Eun Young Lee、Youngkwon Kim、Jae Sung Lee、Jaiwook Park

  DOI：10.1002/ejoc.200900274

  日期：2009.6

  By a one-pot process, α,β-unsaturated esters were synthesized in high yield through the Ru-catalyzed oxidation of primary alcohols and the coupling of the resulting aldehydes and stabilized Wittig reagents. The ruthenium catalyst is composed of ruthenium nanoparticles embedded in aluminum oxyhydroxide and can be recovered simply by filtration or decantation.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  通过一锅法，通过 Ru 催化的伯醇氧化以及生成的醛和稳定的 Wittig 试剂的偶联，以高收率合成了 α,β-不饱和酯。钌催化剂由嵌入羟基氧化铝中的钌纳米颗粒组成，可以简单地通过过滤或倾析回收。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• A novel mode of access to polyfunctional organotin compounds and their reactivity in Stille cross-coupling reaction
  作者：Sandrine Lamandé-Langle、Mohamed Abarbri、Jérôme Thibonnet、Alain Duchêne

  DOI：10.1016/j.jorganchem.2009.03.030

  日期：2009.7

  Mono-, di-, tri- and tetra-functional organotin compounds were easily prepared in a sonicated Barbier reaction using ultrasound technology via coupling reaction of organo halides with tin halides (Bu3SnCl, Bu2SnCl2, BuSnCl3, SnCl4) mediated by magnesium metal. The di- and tri- functional organotin compounds were tested in a Stille cross-coupling reaction in order to ascertain how many groups were transferred. (C) 2009 Elsevier B.V. All rights reserved.
• Catalytic <i>Geminal</i> Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres
  作者：Felix Scheidt、Jessica Neufeld、Michael Schäfer、Christian Thiehoff、Ryan Gilmour

  DOI：10.1021/acs.orglett.8b03794

  日期：2018.12.21

  A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-Toll as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include alpha-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.
• Catalytic Enantioselective Dibromination of Allylic Alcohols
  作者：Dennis X. Hu、Grant M. Shibuya、Noah Z. Burns

  DOI：10.1021/ja4083182

  日期：2013.9.4

  A new dibromination reaction involving the combination of dibromomalonate as the bromonium source and a titanium bromide species as the bromide source has been developed. Enantioselective catalysis has been achieved through apparent ligand acceleration by a tartaric acid-derived diol.

  已经开发了一种新的二溴化反应，涉及将二溴丙二酸作为溴源和溴化钛物种作为溴源的组合。酒石酸衍生的二醇通过明显的配体加速实现了对映选择性催化。