3-(2-thiophenyl)-acrylic acid butyl ester | 1135-50-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(2-thiophenyl)-acrylic acid butyl ester
• 英文别名: 3-(2-thienyl)propenoic acid butyl ester；butyl 3-(2-thienyl) propenoate；Butyl 3-(thiophen-2-yl)acrylate；butyl 3-thiophen-2-ylprop-2-enoate
• CAS: 1135-50-8
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: OYMYFHYKODAGPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘噻吩 、 丙烯酸丁酯 在 [1.1-bis(diphenilphosphino)cobaltocenium hexafluorophosphate] 、 三乙胺 、 palladium dichloride 作用下， 反应 3.0h， 以93%的产率得到3-(2-thiophenyl)-acrylic acid butyl ester
  参考文献：
  名称：

  An Efficient and Recyclable Catalytic System: PdCl2-Dppc+-PF6 –-[bmim][PF6] for Heck Coupling Reaction

  摘要：

  一种高效的PdCl2-Dppc+-PF6–-[bmim][PF6]催化体系已被开发，用于各种芳基碘化物与烯烃的Heck偶联反应。该催化体系使偶联反应顺利进行，并且产率优异，能够循环使用5次，活性损失极小。

  DOI：

  10.14233/ajchem.2015.17749

文献信息

• 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。
• Air‐Stable Fe₃O₄@SiO₂‐EDTA‐Ni(0) as an Efficient Recyclable Magnetic Nanocatalyst for Effective Suzuki‐Miyaura and Heck Cross‐Coupling via Aryl Sulfamates and Carbamates
  作者：Iman Dindarloo Inaloo、Sahar Majnooni、Hassan Eslahi、Mohsen Esmaeilpour

  DOI：10.1002/aoc.5662

  日期：2020.8

  The synthesis of inexpensive and novel air‐stable Ni(0) nanoparticles immobilized on the EDTA‐modified Fe3O4@SiO2 nanocatalyst was investigated in Suzuki‐Miyaura and Heck cross‐coupling reactions. This catalytic system displayed a greatly improved substrate scope for the carbon–carbon bond formations starting from a wide range of green and economical electrophiles aryl and heteroaryl carbamates and

  廉价且新颖的，稳定的，稳定在EDTA修饰的Fe 3 O 4 @SiO 2上的Ni（0）纳米颗粒的合成在Suzuki-Miyaura和Heck交叉偶联反应中研究了纳米催化剂。该催化体系通过在温和，操作简单的反应条件下通过高效方法，从广泛的绿色和经济亲电氨基甲酸酯和杂芳基氨基甲酸酯和氨基磺酸盐开始，显着改善了碳-碳键形成的底物范围。合成的多相催化剂还通过FT-IR，TEM，XRD，DLS，FE-SEM，UV-Vis，EDX，XPS，TGA，NMR，VSM，ICP和元素分析技术进行了全面表征。可以通过外部磁场容易地回收异质磁性纳米催化剂，并且在催化剂的沥滤可忽略不计并且活性没有实质性降低的情况下，至少七次重复用于接下来的反应至少七次。所有这些亮点使本协议变得有趣，
• Poly(hydroxamic acid) palladium catalyst for heck reactions and its application in the synthesis of Ozagrel
  作者：Shaheen M. Sarkar、Md. Lutfor Rahman、Kwok Feng Chong、Mashitah Mohd Yusoff

  DOI：10.1016/j.jcat.2017.03.023

  日期：2017.6

  Bio-waste corn-cob cellulose supported poly(hydroxamic acid) palladium complex was synthesized and it is characterized using some different techniques such as FTIR, FESEM, HRTEM, EDX, XPS, UV–vis, TGA and ICP-AES analyses. The cellulose supported heterogeneous palladium complex showed high stability and catalytic activity toward Mizoroki-Heck reaction of aryl/heteroaryl halides and arenediazonium tetrafluoroborate

  合成了生物废物玉米芯纤维素负载的聚（异羟肟酸）钯复合物，并使用一些不同的技术对其进行了表征，例如FTIR，FESEM，HRTEM，EDX，XPS，UV-vis，TGA和ICP-AES分析。纤维素负载的异种钯络合物对芳基/杂芳基卤化物和四氟硼酸芳族重氮鎓与各种烯烃的Mizoroki-Heck反应表现出高稳定性和催化活性，从而以高达97％的收率得到相应的偶联产物。钯配合物还用于Ozagrel血栓烷A2合成酶抑制剂Ozagrel的合成，具有优异的收率。通过简单的过滤将配合物从反应混合物中分离出来，并重复使用多达7次，而不会显着降低其催化性能。
• Synthesis and applications of polymeric N-heterocyclic carbene palladium complex-grafted silica as a novel recyclable nano-catalyst for Heck and Sonogashira coupling reactions
  作者：Bahman Tamami、Fatemeh Farjadian、Soheila Ghasemi、Hamed Allahyari

  DOI：10.1039/c3nj41137k

  日期：——

  A new catalytic system based on palladium nanoparticles supported on polymeric N-heterocyclic carbene-grafted silica (Si–PNHC–Pd) is introduced. Aminopropylsilica was reacted with benzoylchloride to form acrylamidopropylsilica. Onto this functionalized silica, vinylimidazole monomer was copolymerized by free radical polymerization. Poly(vinylimidazole)-grafted silica was treated with methyl iodide to form a quaternary salt of poly(vinylimidazole). Si–PNHC–Pd was obtained by subsequent treatment of imidazolium salt with PdCl2. Determination of Pd content was performed using an inductively coupled plasma (ICP) analyzer and the crystalline character was determined by an XRD technique. The topography and particle size of the catalyst was studied by scanning electron microscopy (SEM), transmission electron microscopy (TEM) and atomic force microscopy (AFM). TEM images showed that palladium was dispersed through the polymer surface in nano particle size. This catalytic system exhibited excellent activity in Heck and Sonogashira coupling reactions with various aryl halides. The catalyst was successfully re-used up to 12 runs without appreciable change in its activity. High efficiency of the catalyst along with high yields of products, easy purification, large scale synthesis and high TON and TOF are among the advantages of this heterogeneous catalyst.

  一种基于负载在聚合物化的N-杂环卡宾接枝硅（Si-PNHC-Pd）上的钯纳米颗粒的新催化系统被介绍。氨丙基硅烷与苯甲酰氯反应生成丙烯酰胺丙基硅烷。在这个功能化的硅上，乙烯基咪唑单体通过自由基聚合反应共聚。聚（乙烯基咪唑）接枝硅通过与甲基碘反应形成聚（乙烯基咪唑）的四级盐。Si-PNHC-Pd是通过随后处理咪唑盐与PdCl2得到的。钯含量的测定是使用电感耦合等离子体（ICP）分析器进行的，晶体特性是通过XRD技术确定的。催化剂的形貌和粒径是通过扫描电子显微镜（SEM）、透射电子显微镜（TEM）和原子力显微镜（AFM）研究的。TEM图像显示钯通过聚合物表面分散成纳米颗粒大小。这个催化系统在Heck和Sonogashira偶联反应中表现出优秀的活性，可以处理各种芳基卤化物。催化剂成功地重新使用了多达12次，其活性没有明显变化。这个非均相催化剂的优点包括高效率、高产率的产品、易于纯化、大规模合成和高TOF。
• Immobilized NNN Pd-complex on magnetic nanoparticles: efficient and reusable catalyst for Heck and Sonogashira coupling reactions
  作者：Fahimeh Dehghani Firuzabadi、Zahra Asadi、Farhad Panahi

  DOI：10.1039/c6ra22535g

  日期：——

  Sonogashira coupling reactions were performed in the presence of a catalytic amount of this catalyst system (0.5 mol%) and good yields of products were obtained. Due to the magnetic nature of the catalyst it can be separated from the reaction mixture easily by applying an external magnetic field. Heterogeneity tests affirmed that the catalytic activity stayed indefectible during multiple reaction cycles.

  开发了一种高效且易于回收的磁性纳米粒子负载的钯催化剂，并将其应用于Heck和Sonogashira反应中，以显示其在Pd催化的C-C偶联方案中的催化适用性。使用简单的化学方法制备催化剂。首先，制备Fe 3 O 4 @SiO 2纳米粒子与（3-氯丙基）-三甲氧基硅烷（3-CPTMS）反应，以合成氯官能化的磁性纳米粒子（CPS-MNP）。合成的NNN配体与CPS-MNP的取代反应产生CPS-MNPS-NNN配体。最后，将钯物种固定在CPS-MNPS-NNN配体表面提供了CPS-MNPS-NNN-Pd催化剂。使用各种方法（如SEM，TEM，XPS，EDX，CHN，ICP，XRD，FT-IR和VSM技术）对制得的纳米催化剂的结构和形态进行了表征。TEM图像表明，钯催化剂的尺寸在8–15 nm范围内。在催化量的该催化剂体系（0.5mol％）的存在下进行Heck和Sonogashira偶联反应，并获得