1,4-di(2-n-butyloxycarbonyl-trans-vinyl)-benzene

• 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: 1,4-di(2-n-butyloxycarbonyl-trans-vinyl)-benzene
• 英文别名: 1,4-di(2-n-butylcarbonyl-trans-vinyl)-benzene；1,4-di(2-n-butoxycarbonyl-(E)-vinyl) benzene；1,4-Bis[(e)-2-(n-butoxycarbonyl)vinyl]benzene；butyl (E)-3-[4-[(E)-3-butoxy-3-oxoprop-1-enyl]phenyl]prop-2-enoate
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: IXOKMADCBHVWCP-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• <i>N</i>,<i>N</i>-Dimethyl-β-alanine as an Inexpensive and Efficient Ligand for Palladium-Catalyzed Heck Reaction
  作者：Xin Cui、Zhe Li、Chuan-Zhou Tao、Yu Xu、Juan Li、Lei Liu、Qing-Xiang Guo

  DOI：10.1021/ol060585n

  日期：2006.6.1

  phosphine-free ligand than the previously reported ligand, N,N-dimethylglycine, in the Pd-catalyzed Heck reaction for a variety of aryl bromides, aryl iodides, and activated aryl chlorides with a practical turnover number of 10(3). Both kinetic and theoretical studies suggested that N,N-dimethyl-beta-alanine led to faster oxidative addition of an aryl halide to Pd than N,N-dimethylglycine. [reaction: see text]

  在钯催化的多种芳基溴化物，芳基碘化物和碘化物的Heck反应中，N，N-二甲基-β-丙氨酸是一种比以前报道的配体N，N-二甲基甘氨酸更有效的无膦配体。实际营业额为10（3）的活化的芳基氯化物。动力学和理论研究均表明，N，N-二甲基-β-丙氨酸比N，N-二甲基甘氨酸能更快地将芳基卤化物氧化成Pd。[反应：看文字]
• Novel isoxazoline ligand with ferrocene backbone: preparation and application in Heck reaction with water as solvent
  作者：Shuyan Yu、Zhiqin Zhang、Zhiyu Yu、Yongjia Shang

  DOI：10.1002/aoc.3176

  日期：2014.8

  Two novel isoxazoline N,N‐bidentate ligands with ferrocene backbone have been synthesized and employed for the palladium‐catalyzed Heck coupling reaction. Among them, 1,3‐bis‐(5‐ferrocenylisoxazoline‐3‐yl)benzene was found to be thermally stable and a highly effective ligand for Heck coupling reaction in neat water without N2 protection, affording the desired coupling products in good to excellent

  合成了两个具有二茂铁骨架的新型异恶唑啉N，N双齿配体，并将其用于钯催化的Heck偶联反应。其中，1,3-双（5-二茂铁基异恶唑啉-3-基）苯具有良好的热稳定性，是在没有N 2保护的纯水中进行Heck偶联反应的高效配体，可提供所需的偶联产物具有非对映选择性高的优异收率。发达的催化体系对于1,2-二取代的烯烃也很适用，而后者因其较大的空间位阻而较少参与Heck反应。版权所有©2014 John Wiley＆Sons，Ltd.
• Supramolecular Catalysts by Encapsulating Palladium Complexes within Dendrimers
  作者：Masahiko Ooe、Makoto Murata、Tomoo Mizugaki、Kohki Ebitani、Kiyotomi Kaneda

  DOI：10.1021/ja038455m

  日期：2004.2.1

  architectures, dendrimers encapsulating various catalytically active species can be prepared, which often bring about unique catalysis. Treatment of the alkylated PPI dendrimer with 4-diphenylphosphinobenzoic acid and [PdCl(C3H5)]2 afforded the dendrimer-encapsulated Pd complex using ionic interactions. The dendrimers encapsulating Pd complexes acted as unique supramolecular catalysts for the Heck reaction

  树枝状聚合物是定义明确且高度支化的大分子。通过利用它们的胶囊结构，可以制备封装各种催化活性物质的树枝状聚合物，这通常会带来独特的催化作用。用 4-二苯基膦基苯甲酸和 [PdCl(C3H5)]2 处理烷基化 PPI 树枝状聚合物，通过离子相互作用得到树枝状聚合物包裹的 Pd 复合物。封装 Pd 配合物的树枝状大分子充当 Heck 反应和烯丙基胺化的独特超分子催化剂。树枝状聚合物内部密集的氨基所产生的特定纳米环境可以为 Pd 配合物提供高催化活性和稳定性。通过热变形系统可以实现树枝状催化剂的轻松回收。
• Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction
  作者：Ai-E Wang、Jian-Hua Xie、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1016/j.tet.2004.10.049

  日期：2005.1

  A new type of triaryl phosphine-functionalized imidazolium salts 6 were prepared. Their palladium complexes, generated in situ, were successfully applied in the palladium-catalyzed Heck reaction. Using 1 mol% of Pd(dba)(2) and 10 mol% 6c in the presence of 2 equiv of K2CO3 in DMAc has proven to be highly efficient for the coupling of a wide array of aryl bromides and iodides with acrylates in excellent yield. The coupling of 4-bromotoluene with various styrene derivatives catalyzed by Pd/6c complex also gave good results. (C) 2004 Elsevier Ltd. All rights reserved.
• Facile route to dihydroindacene type ligands using multiple Heck reactions on aryl polybromides
  作者：Alberto Ceccon、Laura Crociani、Saverio Santi、Alfonso Venzo、Andrea Biffis、Giovanni Boccaletti

  DOI：10.1016/s0040-4039(02)02087-7

  日期：2002.11

  The Heck reaction of aryl dibromides and n-butyl acrylate catalyzed by Pd(OAc2/pO-Bu), is a high yielding method to produce intermediates for dihydroindacene type ligands. The same synthetic strategy, extended to tribromides, represents a simple route also to tridentate ligands potentially useful in the stabilization of trimeric metal complexes and clusters. (C) 2002 Elsevier Science Ltd. All rights reserved.