(E)-ethyl 3-(3-((tert-butyldimethylsilyl)oxy)phenyl)acrylate | 1015081-10-3

• 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: (E)-ethyl 3-(3-((tert-butyldimethylsilyl)oxy)phenyl)acrylate
• 英文别名: ethyl (E)-3-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-enoate
• CAS: 1015081-10-3
• 化学式: C₁₇H₂₆O₃Si
• 分子量: 306.477
• InChiKey: GYFFYZVQKOPTBB-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(3-((tert-butyldimethylsilyl)oxy)phenyl)acrylate 在 sulfated SnO₂ 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以98%的产率得到(E)-3-(3-羟基苯基)丙烯酸乙酯
  参考文献：
  名称：

  使用硫酸化 SnO2 作为固体催化剂对叔丁基二甲基甲硅烷基醚进行简便且高度选择性的脱保护

  摘要：

  摘要 已经描述了使用硫酸化 SnO2 作为有效固体催化剂在室温下对叔丁基二甲基甲硅烷基醚进行高选择性脱保护。

  DOI：

  10.1080/00397910701767056
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 3-(叔丁基二甲基硅氧基)苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.5h， 生成 (E)-ethyl 3-(3-((tert-butyldimethylsilyl)oxy)phenyl)acrylate
  参考文献：
  名称：

  Dialkylzinc-mediated allylic polyfluoroarylation reaction

  摘要：

  We present an allylic polyfluoroarylation reaction with broad substrate scope and excellent functional group tolerance, using organozinc reagents under mild conditions. A catalytic amount of triphenylphosphine oxide efficiently promotes iodine-zinc exchange reaction between polyfluoroaryl iodide and dimethylzinc, and the resulting phosphine oxide-activated polyfluoroarylzinc undergoes substitution reaction with allylic halides to afford the corresponding polyfluoroarylated products. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.107

文献信息

• Dual Ligand-Enabled Nondirected C−H Olefination of Arenes
  作者：Hao Chen、Philipp Wedi、Tim Meyer、Ghazal Tavakoli、Manuel van Gemmeren

  DOI：10.1002/anie.201712235

  日期：2018.2.23

  The application of the Pd‐catalyzed oxidative C−H olefination of arenes, also known as the Fujiwara–Moritani reaction, has traditionally been limited by the requirement for directing groups on the substrate or the need to use the arene in large excess, typically as a (co)solvent. Herein the development of a catalytic system is described that, through the combined action of two complementary ligands

  传统上，Pd催化芳烃的氧化CH H烯化反应（也称为Fujiwara-Moritani反应）的应用受到在基团上引导基团的要求或大量使用芳烃的需求的限制，通常是（共）溶剂。本文描述了一种催化系统的开发，该催化系统通过两个互补配体的共同作用，使得首次将无直接基团的芳烃用作限制试剂成为可能。反应在空间控制和电子控制的结合下进行，并且能够将这种强大的反应应用于有价值的芳烃，而这些芳烃不能过量利用。
• One-pot Wittig reaction for the synthesis of α,β-unsaturated esters using highly basic magnesium/lanthanum mixed oxide
  作者：M. Lakshmi Kantam、K.B. Shiva Kumar、V. Balasubramanyam、G.T. Venkanna、F. Figueras

  DOI：10.1016/j.molcata.2010.01.012

  日期：2010.4.14

  Highly basic Mg/La mixed oxide (Mg/La MO) is an effective heterogeneous base, at room temperature for the one-pot Wittig reaction involving aldehyde, a-halo esters and triphenylphosphine to afford alpha,beta-unsaturated esters in good yields with high E-stereoselectivity. Mg/La mixed oxide was recovered quantitatively by simple filtration and reused. The basic properties of Mg/La mixed oxide have been compared to those of nanocrystalline magnesium oxide using the microcalorimetric adsorption of CO2. and the reactivity for Wittig reactions. Mg/La mixed oxide is a stronger base than magnesium oxide (MgO) but shows a much smaller number of sites. Hammett correlations have been determined for both bases and show that the reaction is base mediated, with values of rho = 1.7 for Mg/La mixed oxide, and 1.1 for nanocrystalline magnesium oxide, and a compensation effect can then be observed. (C) 2010 Elsevier B.V. All rights reserved.
• Facile and Highly Selective Deprotection of <i>tert</i>‐Butyldimethyl Silyl Ethers using Sulfated SnO₂ as a Solid Catalyst
  作者：Mahesh H. Bhure、Indresh Kumar、Arun D. Natu、Chandrashekhar V. Rode

  DOI：10.1080/00397910701767056

  日期：2008.1.1

  Abstract Highly selective deprotection of tert‐butyldimethylsilyl ethers at room temperature has been described using sulfated SnO2 as an efficient solid catalyst.

  摘要 已经描述了使用硫酸化 SnO2 作为有效固体催化剂在室温下对叔丁基二甲基甲硅烷基醚进行高选择性脱保护。
• Dialkylzinc-mediated allylic polyfluoroarylation reaction
  作者：Daisuke Kurauchi、Keiichi Hirano、Hisano Kato、Tatsuo Saito、Kazunori Miyamoto、Masanobu Uchiyama

  DOI：10.1016/j.tet.2015.05.107

  日期：2015.9

  We present an allylic polyfluoroarylation reaction with broad substrate scope and excellent functional group tolerance, using organozinc reagents under mild conditions. A catalytic amount of triphenylphosphine oxide efficiently promotes iodine-zinc exchange reaction between polyfluoroaryl iodide and dimethylzinc, and the resulting phosphine oxide-activated polyfluoroarylzinc undergoes substitution reaction with allylic halides to afford the corresponding polyfluoroarylated products. (C) 2015 Elsevier Ltd. All rights reserved.