(E)-ethyl 3-(5-bromo-2-methoxyphenyl)acrylate | 540778-82-3

• 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-(5-bromo-2-methoxyphenyl)acrylate
• 英文别名: 2-Propenoicacid,3-(5-bromo-2-methoxyphenyl)-,ethylester,(2E)-；ethyl (E)-3-(5-bromo-2-methoxyphenyl)prop-2-enoate
• CAS: 540778-82-3
• 化学式: C₁₂H₁₃BrO₃
• 分子量: 285.137
• InChiKey: HGUVBHRXCRZDOI-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-(5-bromo-2-methoxyphenyl)acrylate 、 3-(1-adamantyl)-4-benzyloxyphenylboronic acid 生成 ethyl (E)-5-[3-(1-adamantyl)-4-benzyloxyphenyl]-2-methoxycinnamate
  参考文献：
  名称：

  Induction of apoptosis in cancer cells

  摘要：

  本发明提供了诱导或抑制凋亡或在细胞周期停滞之前发生的凋亡的化合物。此外，本发明提供了用于治疗患有白血病或其他形式癌症的哺乳动物或治疗由细胞凋亡引起的疾病状况的药物组合物和方法。

  公开号：

  US20030176506A1
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(E)-ethyl 3-(5-bromo-2-methoxyphenyl)acrylate
  参考文献：
  名称：

  Induction of apoptosis in cancer cells

  摘要：

  本发明提供了诱导或抑制凋亡或在细胞周期停滞之前发生的凋亡的化合物。此外，本发明提供了用于治疗患有白血病或其他形式癌症的哺乳动物或治疗由细胞凋亡引起的疾病状况的药物组合物和方法。

  公开号：

  US20030176506A1

文献信息

• An improved preparation of mesoporous silica-supported Pd as sustainable catalysts for phosphine-free Suzuki-Miyaura and Heck coupling reactions
  作者：Basudeb Basu、Susmita Paul

  DOI：10.1002/aoc.3036

  日期：2013.10

  An improved and eco‐friendly procedure has been developed to generate mesoporous silica‐supported palladium nanoparticles (SiO2@PdNP) that could be used as a sustainable heterogeneous Pd catalyst for phosphine‐free Suzuki–Miyaura and Heck coupling reactions with excellent turnover number and turnover frequency. The presence of Pd on the silica surface was detected by X‐ray diffraction and the structural

  已开发出一种改进的，环保的方法来生成介孔二氧化硅负载的钯纳米粒子（SiO 2 @PdNP），可用作无磷铃木-宫浦和Heck偶联反应的可持续多相Pd催化剂，具有优异的周转率和周转频率。通过X射线衍射检测二氧化硅表面上Pd的存在，并通过透射电子显微镜获得SiO 2 @PdNP的结构形态。非均相催化体系是可回收的，并且在反应之后没有明显地观察到金属的浸出。版权所有©2013 John Wiley＆Sons，Ltd.
• BF₃·OEt₂-mediated syn-selective Meyer–Schuster rearrangement of phenoxy propargyl alcohols for Z-β-aryl-α,β-unsaturated esters
  作者：Surendra Puri、Madala Hari Babu、Maddi Sridhar Reddy

  DOI：10.1039/c6ob01090c

  日期：——

  1-aryl-3-phenoxy propargyl alcohols is achieved via a BF3-mediated syn-selective Meyer–Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.

  通过在环境条件下通过BF 3介导的顺选择性Meyer-Schuster重排，可以从容易获得的1-芳基-3-苯氧基炔丙基醇合成Z -β-芳基-α，β-不饱和酯。假定该反应机理涉及丙二烯中间体的亲电子硼化，这是动力学控制立体选择性的关键步骤。
• Palladium Supported on a Polyionic Resin as an Efficient, Ligand-Free, and Recyclable Catalyst for Heck, Suzuki-Miyaura, and Sonogashira Reactions
  作者：Basudeb Basu、Fredrik Almqvist、Sajal Das、Pralay Das、Bablee Mandal、Dipanjan Banerjee

  DOI：10.1055/s-0028-1088003

  日期：2009.4

  could be soaked with palladium(0) from palladium salts, the formate counteranion being the reducing source. The resulting Amberlite resin formate supported with palladium(0), ARF-Pd, showed excellent catalytic activity in Heck, Suzuki­-Miyaura, and Sonogashira couplings with a range of substrates. The catalyst may be recovered easily and quantitatively without leaching and recycled; it was tested for

  可以通过用甲酸水溶液简单漂洗而得自市售Amberlite树脂氯化物的聚离子Amberlite树脂甲酸盐（ARF）可以用钯盐中的钯（0）浸泡，甲酸的抗衡阴离子是还原性来源。负载有钯（0），ARF-Pd的所得Amberlite树脂甲酸酯在Heck，Suzuki-Miyaura和Sonogashira偶联剂中与多种底物均表现出出色的催化活性。该催化剂可以容易地定量回收而无需浸出和再循环。对它进行了五次运行测试，没有任何明显的活性损失。 Amberlite树脂-CC偶联-非均相催化-钯
• Catalyst containing covalently bonded formate groups and Pd(0) and process for its obtention
  申请人：Almquest AB

  公开号：EP1994983A1

  公开（公告）日：2008-11-26

  1. A method of producing a heterogeneous catalyst suitable for catalyzing Heck, Suzuki-Miyaura and Buchwald-Hartwig reactions, comprising the steps of: a) providing a porous carrier, said porous carrier consisting of a core and a plurality of ion exchange groups covalently bonded to the surface of said core, where at least 90 % of the ions bound to said carrier are formate ions; b) providing a palladium (II) salt; c) suspending said carrier in an organic solvent thereby obtaining a suspension; d) adding said palladium salt to said suspension and allowing the resulting mixture to react at a temperature within the range of 30 - 70 °C until said carrier has turned black; e) washing said carrier in water; and f) drying said carrier under vacuum; characterised in that the resulting carrier subsequently is resuspended in dimethyl formamide and heated under inert atmosphere to at least 90 °C for 2 hours followed by washing with a polar solvent and drying. The invention also relates to a catalyst produced by the method and to processes where the catalyst is used for catalysing Heck, Suzuki-Miyaura, and Buchwald-Hartwig reactions.

  一种制备适用于催化Heck、Suzuki-Miyaura和Buchwald-Hartwig反应的非均相催化剂的方法，包括以下步骤： a）提供多孔载体，该多孔载体由核心和多个离子交换基团共价键合到核心表面组成，其中至少90％的离子结合到该载体上为甲酸根离子； b）提供钯（II）盐； c）将该载体悬浮在有机溶剂中，从而获得悬浮液； d）将该钯盐加入该悬浮液中，并允许所得混合物在30-70℃的温度范围内反应，直到该载体变黑； e）用水洗涤该载体； f）在真空下干燥该载体； 其特征在于，随后所得的载体在惰性气氛下在二甲基甲酰胺中重悬并加热至至少90℃，持续2小时，然后用极性溶剂洗涤并干燥。 该发明还涉及由该方法制备的催化剂以及使用该催化剂催化Heck、Suzuki-Miyaura和Buchwald-Hartwig反应的过程。
• CATALYST
  申请人：Almqvist Fredrik

  公开号：US20100119424A1

  公开（公告）日：2010-05-13

  The present invention relates to a method of producing a heterogeneous catalyst suitable for catalyzing Heck, Suzuki-Miyaura Sonogashira coupling and Buchwald-Hartwig reactions, comprising the steps of: a) providing a macroporous carrier, said macroporous carrier consisting of a core and a plurality of ion exchange groups covalently bonded to the surface of said core, where at least 90% of the ions bound to said carrier are formate ions; b) swelling said carrier in a polar solvent; c) providing a palladium (II) salt; d) suspending said carrier in an organic solvent thereby obtaining a suspension; e) adding said palladium salt to said suspension and allowing the resulting mixture to react at a temperature within the range of 0 70° C. until said carrier has turned black; f) washing said carrier in water; g) drying said carrier under vacuum.

  本发明涉及一种生产适用于催化Heck、Suzuki-Miyaura Sonogashira偶联和Buchwald-Hartwig反应的杂多相催化剂的方法，包括以下步骤：a）提供一种大孔载体，所述大孔载体由核心和多个离子交换基团共价键合到所述核心表面组成，其中至少90％的离子结合到所述载体上是甲酸根离子；b）在极性溶剂中使载体膨胀；c）提供钯（II）盐；d）将所述载体悬浮在有机溶剂中，从而得到一种悬浮液；e）将所述钯盐加入所述悬浮液中，并在0-70℃的温度范围内使所得混合物反应，直至所述载体变黑；f）在水中清洗所述载体；g）在真空下干燥所述载体。