(E)-2-(4-(4-methoxystyryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1169942-90-8

• 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: (E)-2-(4-(4-methoxystyryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[4-[(E)-2-(4-methoxyphenyl)ethenyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1169942-90-8
• 化学式: C₂₁H₂₅BO₃
• 分子量: 336.239
• InChiKey: OMXDZANFIQFIPA-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-(4-methoxystyryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 四(三苯基膦)钯 、 palladium on activated charcoal 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 16.17h， 生成 4'-(4-methoxyphenethyl)-[1,1'-biphenyl]-4-carbaldehyde
  参考文献：
  名称：

  Olefin cross-metathesis/Suzuki–Miyaura reactions on vinylphenylboronic acid pinacol esters

  摘要：

  A series of alkenyl phenylboronic acid pinacol esters has been synthesized via an olefin cross-metathesis reaction of vinylphenylboronic acid pinacol ester derivatives. After catalytic hydrogenation, the resulting boronates were coupled via a microwave-mediated Suzuki-Miyaura reaction to afford a library of biarylethyl aryl and biarylethyl cycloalkyl derivatives. A complementary reaction sequence involved an initial Suzuki-Miyaura coupling. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.081
• 作为产物：
  描述：

  4-乙烯苯硼酸频那醇酯 在 bis(triphenylphosphine)nickel(II) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 19.08h， 生成 (E)-2-(4-(4-methoxystyryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  中断的Pummerer /镍催化交叉偶联序列

  摘要：

  已经开发了一种中断的Pummerer /镍催化的交叉偶联策略，并将其用于苯乙烯的精制。操作简单的方法可以作为一个锅法进行，涉及直接形成稳定的烯基sulf盐中间体，利用市售的亚砜，催化剂和配体，在环境温度下操作，可容纳sp‐，sp 2‐，和sp 3杂交的有机锌偶联伙伴，并通过两个步骤以高收率提供官能化的苯乙烯产品。中断的Pummerer /环化方法也已用于获得碳和杂环烯基sulf盐进行交叉偶联。

  DOI：

  10.1002/anie.201805396

文献信息

• Convenient methods for preparing π-conjugated linkers as building blocks for modular chemistry
  作者：Jiří Kulhánek、Filip Bureš、Miroslav Ludwig

  DOI：10.3762/bjoc.5.11

  日期：——

  and optimized procedures for preparing extended pi-conjugated linkers are described. Either unsubstituted or 4-donor substituted pi-linkers bearing a styryl, biphenyl, phenylethenylphenyl, and phenylethynylphenyl pi-conjugated backbone are functionalized with boronic pinacol esters as well as with terminal acetylene moieties allowing their further use as building blocks in Suzuki-Miyaura or Sonogashira

  描述了用于制备扩展π共轭接头的简单、直接和优化的程序。带有苯乙烯基、联苯、苯基乙烯基苯基和苯基乙炔基苯基π-共轭主链的未取代或4-供体取代的π-连接体用硼频哪醇酯以及末端乙炔部分进行功能化，允许它们进一步用作Suzuki-Miyaura或Sonogashira中的结构单元偶联反应。
• One-Step Preparation of Functionalized (<i>E</i>)-Vinylsilanes from Aldehydes
  作者：Diane S. W. Lim、Edward A. Anderson

  DOI：10.1021/ol201833u

  日期：2011.9.16

  Functionalized (E)-vinylsilanes have been prepared in one step from a wide range of aldehydes, via a chromium(II)-mediated olefination with novel dihalomethylsilane reagents, in moderate to excellent yields and with excellent stereoselectivity.

  官能化的（E）-乙烯基硅烷一步一步地由各种醛类制备，通过铬（II）介导的新型二卤代甲基硅烷试剂的烯化反应，以中等至极好的收率和极好的立体选择性而制得。
• Novel Carbazole‐Based<i>N</i>‐Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd‐Catalyzed Coupling Processes
  作者：Tejpalsingh Ramsingh Girase、Anant R. Kapdi

  DOI：10.1002/asia.201900419

  日期：2019.8

  A series of new carbazole‐based N‐heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole‐based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol

  一系列新的咔唑基氮杂环卡宾（NHC）配体已通过简单且容易的合成路线进行合成，随后用于基于Pd /咔唑的NHC催化体系中，发现该化合物可有效催化Heck反应，以高收率提供取代的二苯乙烯衍生物。合成了几种具有生物活性的对苯二酚，包括萜烯，松油基乙烯基，三甲氧基白藜芦醇和白藜芦醇，而且三甲氧基白藜芦醇的放大倍数也达到了10 mmol。通过一锅法进行双串联化学选择性Heck反应，然后进行Miyaura硼化，可以扩展合成的应用范围，从而可以一步一步获得合成上有用的二苯乙烯基硼酸酯。相似地，
• Controlling Reactivity and Selectivity in the Mizoroki–Heck Reaction: High Throughput Evaluation of 1,5-Diaza-3,7-diphosphacyclooctane Ligands
  作者：Eric S. Isbrandt、Devon E. Chapple、Nguyen Thien Phuc Tu、Victoria Dimakos、Anne Marie M. Beardall、Paul D. Boyle、Christopher N. Rowley、Johanna M. Blacquiere、Stephen G. Newman

  DOI：10.1021/jacs.3c14612

  日期：2024.2.28

  We report a high throughput evaluation of the Mizoroki–Heck reaction of diverse olefin coupling partners. Comparison of different ligands revealed the 1,5-diaza-3,7-diphosphacyclooctane (P2N2) scaffold to be more broadly applicable than common “gold standard” ligands, demonstrating that this family of readily accessible diphosphines has unrecognized potential in organic synthesis. In particular, two

  我们报告了对不同烯烃偶联伙伴的 Mizoroki-Heck 反应的高通量评估。不同配体的比较表明，1,5-二氮杂-3,7-二磷环辛烷 (P 2 N 2 ) 支架比常见的“金标准”配体具有更广泛的适用性，表明这一易于获得的二膦家族在有机领域具有未被认识到的潜力。合成。特别是，鉴定出两个结构相关的P 2 N 2配体能够实现苯乙烯的区域发散芳基化。通过简单地将磷取代基从苯基改为叔丁基，可以以高区域异构比获得直链和支链 Mizoroki-Heck 产物。进行了实验和计算机制研究以进一步探讨选择性的起源，这表明两种配体以类似的方式与金属配位，但磷取代基的刚性定位迫使与引入的烯烃以 π-π 相互作用接触（对于P-Ph 配体）或空间冲突（对于 P -t Bu 配体），决定了区域控制。
• Alkyne Semihydrogenation with a Well-Defined Nonclassical Co–H₂ Catalyst: A H₂ Spin on Isomerization and <i>E</i>-Selectivity
  作者：Kenan Tokmic、Alison R. Fout

  DOI：10.1021/jacs.6b08128

  日期：2016.10.19

  The reactivity of a co(I)-H-2 complex was extended toward the semihydrogenation of internal alkynes. Under ambient temperatures and moderate pressures of H-2, a broad scope of alkynes were semihydrogenated using a Co-I-N-2 precatalyst, resulting in the formation of trans-alkene products. Furthermore, mechanistic studies using H-1, H-2, and parahydrogen induced polarization (PHIP) transfer NMR spectroscopy revealed cis -hydrogenation of the alkyne occurs first. The Co-mediated alkene isomerization afforded the E-selective products from a broad group of alkynes with good yields and E/Z selectivity.