butyl (E)-4-bromocinnamate

• 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: butyl (E)-4-bromocinnamate
• 英文别名: (E)-butyl 3-(4-bromophenyl)acrylate；butyl (E)-3-(4-bromophenyl)acrylate；(E)-n-butyl 3-(4-bromophenyl)acrylate；butyl (E)-3-(4-bromophenyl)prop-2-enoate
• 化学式: C₁₃H₁₅BrO₂
• 分子量: 283.165
• InChiKey: PIQCRXRHGULAGW-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  丙烯酸丁酯 、 butyl (E)-4-bromocinnamate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以62%的产率得到1,4-di(2-n-butyloxycarbonyl-trans-vinyl)-benzene
  参考文献：
  名称：

  Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

  摘要：

  An efficient method was developed for the oxidative Heck reaction between arylboronic acids and olefins catalyzed by anionic palladium complexes of the type [CA](x)[PdCl4] (x = 1,2) and [CA](2)[Pd2Cl6] (CA= imidazolium or pyridinium cation). Molecular oxygen was employed as an environmentally benign oxidant to regenerate Pd(II) species during the reaction. The elaborated protocol could be applied to the coupling of different arylboronic acids with both electron-rich and electron-poor olefins. The catalyst system was further employed for the one-pot oxidative Heck reaction followed by the Heck coupling to build conjugated compounds in good yield.Mass spectrometry (ESI-MS) and UV-vis spectroscopy was used to identify palladium-containing complexes in the reactions. A plausible reaction mechanism of the oxidative Heck reaction was proposed. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.07.003
• 作为产物：
  描述：

  4-溴苯甲酰氯 在 三乙胺 、 palladium dichloride 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基乙酰胺 为溶剂， 反应 19.0h， 生成 butyl (E)-4-bromocinnamate
  参考文献：
  名称：

  N-酰基糖精通过化学选择性N-C裂解作为基于酰胺的酰化试剂：Pd催化的脱羰Heck反应

  摘要：

  通过使用N-酰基糖精作为偶联伙伴的化学选择性N-C活化，实现了钯催化的酰胺脱羰Heck反应。这些研究仅代表迄今为止报道的酰胺-Heck反应的第二个例子。各种各样的电子上不同的酰胺和烯烃偶合伙伴都适合这种转化。据报道，通过C–B​​r / N–C裂解进行正交位点选择性Heck交叉偶联和机理研究。该报告介绍了易于获得，稳定，便宜和良性的N-酰基糖精作为芳基转移试剂，以获取通用的芳基金属中间体。

  DOI：

  10.1021/acs.joc.6b02294

文献信息

• Continuous Flow Palladium(II)-Catalyzed Oxidative Heck Reactions with Arylboronic Acids
  作者：Luke R. Odell、Jonas Lindh、Tomas Gustafsson、Mats Larhed

  DOI：10.1002/ejoc.201000063

  日期：2010.4

  Palladium(II)-catalyzed oxidative Heck reactions were investigated under continuous flow conditions. Selective, fast and convenient protocols for the coupling of arylboronic acids with electron-rich and electron-poor olefins were developed by using a commercially available flow reactor.

  在连续流动条件下研究了钯 (II) 催化的氧化 Heck 反应。通过使用市售流动反应器开发了用于将芳基硼酸与富电子和缺电子烯烃偶联的选择性、快速和方便的方案。
• Rhodium(II)-Catalyzed Nondirected Oxidative Alkenylation of Arenes: Arene Loading at One Equivalent
  作者：Harit U. Vora、Anthony P. Silvestri、Casper J. Engelin、Jin-Quan Yu

  DOI：10.1002/anie.201310539

  日期：2014.3.3

  bimetallic RhII catalyst promoted the CH alkenylation of simple arenes at 1.0 equivalent without the use of a directing group. A phosphine ligand as well as cooperative reoxidation of RhII with Cu(TFA)2 and V2O5 proved essential in providing monoalkenylated products in good yields and selectivities, especially with di‐ and trisubstituted arenes.

  双金属的Rh II催化剂促进与c  H在1.0当量，而无需使用定向基团的简单的芳烃的烯基化。膦配体以及Rh II与Cu（TFA）2和V 2 O 5的协同再氧化被证明对于以高收率和选择性提供单烯基化产物至关重要，特别是对于二取代和三取代的芳烃。
• Pd-Catalyzed Efficient One-Pot Sequential Cross-Coupling Reactions of Aryl Dihalides
  作者：Xiaoming Zhang、Ailing Liu、Wanzhi Chen

  DOI：10.1021/ol801589p

  日期：2008.9.1

  The palladium complex containing N-heterocyclic carbene ligands catalyzes one-pot sequential Heck/Suzuki, Heck/Heck, and Heck/Sonogashira coupling reactions of aryl dihalides to afford unsymmetrically substituted arenes in excellent yields.

  含有N-杂环卡宾配体的钯配合物催化芳基二卤化物的一锅顺序Heck / Suzuki，Heck / Heck和Heck / Sonogashira偶联反应，从而以优异的产率提供不对称取代的芳烃。
• A practical method for heterogeneously-catalyzed Mizoroki–Heck reaction: Flow system with adjustment of microwave resonance as an energy source
  作者：Tomohiro Ichikawa、Masahiro Mizuno、Shun Ueda、Noriyuki Ohneda、Hiromichi Odajima、Yoshinari Sawama、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1016/j.tet.2018.02.044

  日期：2018.4

  The microwave-assisted and continuous-flow Mizoroki–Heck reaction using a heterogeneous palladium catalyst supported on the anion-exchange resin DIAION WA30 (7% Pd/WA30) is described. The microwave resonance is finely adjusted to 2.4 GHz according to the electric permittivity of the reaction medium for efficient heating. Organic solvents, such as acetonitrile, N,N-dimethylacetamide, and toluene, can

  描述了使用负载在阴离子交换树脂DIAION WA30（7％Pd / WA30）上的多相钯催化剂进行的微波辅助连续流Mizoroki-Heck反应。为了有效地加热，根据反应介质的介电常数将微波共振微调至2.4 GHz。乙腈，N，N-二甲基乙酰胺和甲苯等有机溶剂即使在微波辐射强度较低的情况下，也可以在装有7％Pd / WA30的玻璃管形催化剂盒中充分加热，该催化剂盒基于溶剂的介电常数。催化剂盒可以连续重复使用至少5次，而无需更换。
• Direct Oxidative Coupling of Arenes with Olefins by Rh-Catalyzed CH Activation in Air: Observation of a Strong Cooperation of the Acid
  作者：Lu Zheng、Jianhui Wang

  DOI：10.1002/chem.201200657

  日期：2012.7.27

  developed for the oxidative coupling of non‐chelate‐assisted arenes with olefins in the presence of catalytic amounts of Cu(OAc)2⋅H2O as a co‐oxidant and oxygen as the terminal oxidant. The acid was an indispensable component in this system and played a very important role in the coupling reaction. This catalytic system was applied to the direct oxidative coupling of a series of arenes and olefins and the corresponding

  A [的RhCl（COD）} 2 ] /四氯化碳3 COOH系统用于非螯合辅助芳烃的氧化偶联在催化量的Cu的存在开发与烯烃（OAC）2 ⋅ ħ 2 O作为助氧化剂和氧气作为终端氧化剂。酸是该体系中必不可少的组分，并且在偶联反应中起着非常重要的作用。该催化体系用于一系列芳烃和烯烃的直接氧化偶联，相应的产物以高收率提供，具有特殊的化学和区域选择性。该反应为乙烯基芳烃提供了一种原子高效的途径，乙烯基芳烃广泛用于各种精细化学品中。