2-(E-2-bromo-1-ethenyl)-3,4,5-trimethoxybenzene | 312600-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(E-2-bromo-1-ethenyl)-3,4,5-trimethoxybenzene
• 英文别名: (E)-1-(2-bromovinyl)-3,4,5-trimethoxybenzene；(E)-5-(2-bromovinyl)-1,2,3-trimethoxybenzene；5-[(E)-2-bromovinyl]-1,2,3-trimethoxybenzene；(E)-β-bromo-3,4,5-trimethoxystyrene；(E)-3,4,5-trimethoxy-β-bromostyrene；5-(2-Bromoethenyl)-1,2,3-trimethoxybenzene；5-[(E)-2-bromoethenyl]-1,2,3-trimethoxybenzene
• CAS: 312600-72-9
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 273.126
• InChiKey: XLIQGJZAJWINPR-SNAWJCMRSA-N

物化性质

• 沸点：
  346.0±37.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-(E-2-bromo-1-ethenyl)-3,4,5-trimethoxybenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  Triazole-curcuminoids: A new class of derivatives for ‘tuning’ curcumin bioactivities?

  摘要：

  Curcumin is a unique blend of pharmacophores responsible for the pleiotropy of this natural pigment. In the present study we have replaced the 1,3-dicarbonyl moiety with a 1,2,3-triazole ring to furnish a new class of triazole-curcuminoids as a possible strategy to generate new compounds with different potency and selectivity compared to curcumin. We obtained a proof-of-principle library of 28 compounds tested for their cytotoxicity (SY-SY5Y and HeLa cells) and for their ability to inhibit NF-kappa B. Furthermore, we also generated 1,3-dicarbonyl curcuminoids of selected click compounds. Triazole-curcuminoids lost their ability to be Michael's acceptors, yet maintained some of the features of the parent compounds and disclosed new ones. In particular, we found that some compounds were able to inhibit NF-kappa B without showing cytotoxicity, while others, unlike curcumin, activated NF-kappa B signalling. This validates the hypothesis that click libraries can be used to investigate the biological activities of curcumin as well as generate analogs with selected features. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.044
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸 在 碘苯二乙酸 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 生成 2-(E-2-bromo-1-ethenyl)-3,4,5-trimethoxybenzene
  参考文献：
  名称：

  四氟吡啶硫化物与卤乙烯光催化交叉偶联合成β,γ-不饱和羰基化合物

  摘要：

  β,γ-不饱和羰基化合物是有机合成和药物化学中的通用结构单元。在此，我们报道了由四氟吡啶硫化物与卤乙烯合成β,γ-不饱和羰基化合物。这种交叉偶联反应利用了光催化和锌催化的优点，锌催化因其毒性较小、地球资源丰富且成本效益高而受到青睐。

  DOI：

  10.1021/acs.joc.3c01800

文献信息

• Illuminating <i>anti</i>-hydrozirconation: controlled geometric isomerization of an organometallic species
  作者：Theresa Hostmann、Tomáš Neveselý、Ryan Gilmour

  DOI：10.1039/d1sc02454j

  日期：——

  reaction product functions as an efficient in situ generated photocatalyst. Coupling of the E-vinyl zirconium species with an alkyne unit generates a conjugated diene: this has been leveraged as a selective energy transfer catalyst to enable E → Z isomerization of an organometallic species. Through an Umpolung metal–halogen exchange process (Cl, Br, I), synthetically useful vinyl halides can be generated

  据报道，实现芳基乙炔正式反加氢锆化的一般策略是将使用 Schwartz 试剂（Cp 2 ZrHCl）的顺式加氢金属化与随后在λ = 400 nm 处的光介导几何异构化相结合。所述的机理划定禁忌-thermodynamic异构化步骤指示次要反应产物用作高效的原位产生的光催化剂。所述的联接ë与炔烃单元-乙烯基锆物质生成的共轭二烯：这已被利用作为选择性能量转移催化剂以使È → ž有机金属物种的异构化。通过Umpolung金属 - 卤素交换过程（Cl、Br、I），可以生成合成有用的乙烯基卤化物（高达Z  :  E = 90 : 10）。这个支持平台提供了一种策略，可以从简单的芳基乙炔中获取两种几何形式的亲核和亲电烯烃片段。
• Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides
  作者：Weijie Yu、Long Chen、Jiasi Tao、Tao Wang、Junkai Fu

  DOI：10.1039/c9cc00768g

  日期：——

  A novel reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides has been realized via photoredox/nickel dual catalysis to produce vinyl arene derivatives bearing all-carbon quaternary centers with excellent E-selectivity. A stoichiometric metal reductant could be avoided by employing commercially available N,N,N′,N′-tetramethylethylenediamine (TMEDA) as the terminal reductant

  通过光氧化还原/镍双重催化已经实现了芳基乙烯基卤化物和未活化的叔烷基溴化物的新型还原性交叉偶联，以产生具有优异的E-选择性的带有全碳四元中心的乙烯基芳烃衍生物。可以通过使用市售的N，N，N '，N'-四甲基乙二胺（TMEDA）作为末端还原剂来避免化学计量的金属还原剂。
• Copper-mediated trifluoroethoxylation of vinyl bromides
  作者：Jianping Ding、Yi You、Zhiqiang Weng

  DOI：10.1016/j.tetlet.2016.03.023

  日期：2016.4

  Vinyl bromides were subjected to the trifluoroethoxylation reactions with copper reagent [(phen)2Cu][OCH2CF3] at 80 °C in DMF with the presence of NaOt-Bu to afford the trifluoroethyl vinyl ethers in good yields. A range of functional groups, such as cyano, nitro, alkoxy, trifluoromethyl, halide, and heterocyclic groups were well tolerated. This approach is also amenable to being performed out on gram

  在NaO t -Bu存在下，于80℃，在DMF中，使用铜试剂[[phen] 2 Cu] [OCH 2 CF 3 ]对乙烯基溴进行三氟乙氧基化反应，从而以良好的收率得到三氟乙基乙烯基醚。各种官能团，例如氰基，硝基，烷氧基，三氟甲基，卤化物和杂环基均具有良好的耐受性。该方法也适合于以克为单位执行。
• Palladium-Catalyzed Intermolecular Three-Component Coupling of Organic Halides with Alkynes and Alkenes: Efficient Synthesis of Oligoene Compounds
  作者：Kana Shibata、Tetsuya Satoh、Masahiro Miura

  DOI：10.1002/adsc.200700171

  日期：2007.10.8

  intermolecular three-component coupling of aryl or vinyl halides, diarylacetylenes, and monosubstituted alkenes effectively proceeds in the presence of palladium acetate, lithium chloride, and sodium bicarbonate as catalyst, promoter, and base, respectively, in aqueous DMF or DMSO to produce the corresponding 1,3-butadiene or 1,3,5-hexatriene derivatives. Use of dienyl bromides allows the coupling to afford

  芳基或乙烯基卤化物，二芳基乙炔和单取代烯烃的分子间三组分偶联在DMF或DMSO水溶液中分别存在乙酸钯，氯化锂和碳酸氢钠作为催化剂，促进剂和碱的情况下有效进行相应的1，3-丁二烯或1，3，5-己三烯衍生物。使用二烯基溴化物可使偶合反应得到1,3,5,7-辛酸酯。在当前的催化条件下，通过乙烯基溴和二芳基乙炔的1：2偶联而无需添加烯烃也可有效地形成富烯衍生物。
• Multicomponent and one-pot synthesis of trisubstituted pyridines through a Pd-catalyzed cross-coupling/cross-coupling/cycloaddition sequence
  作者：José Barluenga、Agustín Jiménez-Aquino、M. Alejandro Fernández、Fernando Aznar、Carlos Valdés

  DOI：10.1016/j.tet.2007.10.112

  日期：2008.1

  Trisubstituted pyridines are regioselectively synthesized through multicomponent and one-pot processes promoted by a bifunctional Pd-catalyst. The process involves formation of an enamine by Pd-catalyzed amination of an alkenyl bromide, formation of a 2-aza-1,3-butadiene by Pd-catalyzed cross-coupling of a trimethylsilylimine with an alkenyl bromide, and Lewis acid catalyzed cycloaddition between the

  三取代吡啶是通过双功能Pd催化剂促进的多组分和一锅法区域选择性合成的。该方法包括通过钯催化的烯基溴化物的胺化形成烯胺，通过钯催化的三甲基甲硅酰亚胺与烯基溴化物的交叉偶联形成2-氮杂-1,3-丁二烯，以及路易斯酸催化的之间的环加成反应。烯胺和氮杂二烯。