3-(4-cyano-phenyl)-2-propenoic acid ethyl ester | 20655-58-7

• 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: 3-(4-cyano-phenyl)-2-propenoic acid ethyl ester
• 英文别名: ethyl 3-(4-cyanophenyl)acrylate；Ethyl 3-(4-cyanophenyl)prop-2-enoate
• CAS: 20655-58-7
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: NVLBOCIUMFYPGI-UHFFFAOYSA-N

物化性质

• 沸点：
  352.0±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  3-(4-cyano-phenyl)-2-propenoic acid ethyl ester 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 盐酸羟胺 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 38.0h， 生成 4-[3-(5-amino-2-furan-2-ylpyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)propyl]-N-hydroxybenzamidine
  参考文献：
  名称：

  7-Substituted 5-Amino-2-(2-furyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as A_2A Adenosine Receptor Antagonists:  A Study on the Importance of Modifications at the Side Chain on the Activity and Solubility

  摘要：

  It was demonstrated in the early 1990s that adenosine exerts many physiological functions through the interaction with four different receptors, named A(1), A(2A), A(2B), and A(3). In the past few years, our group has been involved in the development of A(2A) antagonists, which led to the synthesis of SCH 58261 (1), the first potent and selective adenosine A(2A) antagonist, which has been widely used as a reference compound. In this paper, we present an extended series of pyrazolotriazolopyrimidines synthesized with the aim to investigate the influence of the substitutions on the pyrazole ring. The choice of the substituents was based on their capability to improve water solubility while retaining high affinity and selectivity at the human A(2A) adenosine receptor subtype. In this series, some structural characteristics that are important for activity, i.e., tricyclic structure, free amino group at 5-position, furan ring, and substituent at 7-position on the pyrazole moiety, have been maintained. We focused our attention on the nature of the phenyl ring substituent to improve water solubility. Following this strategy, we developed new compounds with good affinity and selectivity for A(2A) adenosine receptors, such as 8d (K-i 0.12 nM; hA(1)/hA(2A) ratio = 1025; R-m = 2.8), 8h (K-i 0.22; hA(1)/hA(2A) ratio = 9818; R-m = 3.4), 8i (K-i 0.18 nM; hA(1)/hA(2A) ratio = 994; R-m = 2.8), 8k (K-i 0.13 nM; hA(1)/hA(2A) ratio = 4430; R-m = 3.6), and 14b (K-i 0.19 nM; hA(1)/hA(2A) ratio = 2273; R-m = 2.7). All the new synthesized compounds have no significant interaction with either-A(2B) or A(3) receptor subtypes. This new series of compounds deeply enlightens some structural requirements to display high affinity and selectivity for the A(2A) adenosine receptor subtype, although our goal of identifying new compounds with increased water solubility was not completely achieved. On this basis, other strategies will be devised to improve this class of compounds with a profile that appears to be promising for treatment of neurodegenerative disorders, such as Parkinson's disease.

  DOI：

  10.1021/jm010924c
• 作为产物：
  描述：

  4-溴苯腈 、 丙烯酸乙酯 在 四丁基氯化铵 、 sodium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以88%的产率得到3-(4-cyano-phenyl)-2-propenoic acid ethyl ester
  参考文献：
  名称：

  聚多巴胺上的钯：其在催化转移加氢和Heck偶联反应中的真实潜力

  摘要：

  报道了Pd-聚多巴胺和磁性Fe 3 O 4 @ Pd-聚多巴胺催化剂在催化转移加氢反应和Heck芳基化反应中的应用。尽管发现羰基化合物的还原不太普遍，但可以有效地将带有给电子和吸电子取代基的多种芳香族硝基化合物还原成相应的苯胺。在后一种情况下，仅芳族酮可被还原为相应的醇，而醛底物不受影响，这可能是由于它们与催化剂载体反应导致催化剂失活。通过使用磁性Fe 3 O 4@ Pd-聚多巴胺系统可促进催化剂的回收和连续使用五个周期，而不会导致硝基还原活性的显着降低。Heck反应中催化剂的效率与转移氢化中的效率相当，但是，在这种情况下再利用时未观察到催化活性，这很可能是金属浸出的结果。我们还探索了串联Heck反应/催化转移加氢序列，但是，这两个反应在应用条件下均显示出有限的相容性。

  DOI：

  10.1002/cctc.201700609

文献信息

• Pd-chelated 1,3,5-triazine organosilica as an active catalyst for Suzuki and Heck reactions
  作者：S. Elavarasan、K. Kala、Ibrahim Muhammad、A. Bhaumik、M. Sasidharan

  DOI：10.1016/j.mcat.2019.110521

  日期：2019.10

  condensation reaction between cyanuric chloride and 3-aminopropyl triethoxysilane. The resultant MPMO material serves as an effective solid chelating agent through amine and triazine functionalities for Pd(II) to provide Pd-MPMO. The Pd-MPMO material was thoroughly characterized by a small-angle XRD, HRTEM, N2 sorption, 13C CP-MAS NMR, 29Si CP-MAS NMR, and ICP analyses. The Pd-MPMO serves as an active catalyst

  具有分子水平控制的新型功能性周期性介孔有机硅的设计可用于能源和环境研究的多个领域，包括吸附，催化，纳米技术和能量收集。本文中，我们通过自组装N 2，N 4，N 6提出了三聚氰胺（1,3,5-三嗪）功能化的周期性介孔二氧化硅（MPMO）-三（3-（三乙氧基甲硅烷基）丙基）-1,3,5-三嗪-2,4,6-三胺（TTET）与原硅酸四乙酯（TEOS）通过共聚策略进行。通过氰尿酰氯与3-氨基丙基三乙氧基硅烷之间的缩合反应合成了TTET倍半硅氧烷烷前体。所得的MPMO材料通过Pd（II）的胺和三嗪官能团充当有效的固体螯合剂，从而提供Pd-MPMO。通过小角度XRD，HRTEM，N 2吸附，13 C CP-MAS NMR，29 Si CP-MAS NMR和ICP分析对Pd-MPMO材料进行了全面表征。Pd-MPMO用作C的活性催化剂在无配体和无助催化剂的条件下，通过Suzuki和Heck交叉偶联方法进行
• Cobalt‐Catalyzed Radical Hydroamination of Alkenes with <i>N</i> ‐Fluorobenzenesulfonimides
  作者：Tao Qin、Guowei Lv、Qi Meng、Ge Zhang、Tao Xiong、Qian Zhang

  DOI：10.1002/anie.202110178

  日期：2021.12

  N-fluorobenzenesulfonimide (NFSI) and its analogues as both nitrogen source and oxidant was successfully disclosed. A variety of alkenes, including aliphatic alkenes, styrenes, α, β-unsaturated esters, amides, acids, as well as enones, were all compatible to provide desired amination products. Mechanistic experiments suggest that the reaction underwent a metal-hydride-mediated hydrogen atom transfer (HAT) with alkene

  成功地公开了使用 Co(salen) 作为催化剂、N-氟苯磺酰亚胺 (NFSI) 及其类似物作为氮源和氧化剂的烯烃的有效和通用自由基加氢胺化。各种烯烃，包括脂肪族烯烃、苯乙烯、α, β-不饱和酯、酰胺、酸以及烯酮，都可以提供所需的胺化产物。机理实验表明，该反应与烯烃进行了金属氢化物介导的氢原子转移 (HAT)，然后是关键的催化剂控制原位生成的有机钴 (IV) 物质和氮基亲核试剂之间的类 SN 2 途径。此外，借助改性手性钴 (II)-salen 催化剂，还实现了前所未有的不对称版本，具有良好到出色的对映控制水平。
• Flexible, dicationic imidazolium salts for<i>in situ</i>application in palladium-catalysed Mizoroki-Heck coupling of acrylates under aerobic conditions
  作者：Marilyn Daisy Milton、Parul Garg

  DOI：10.1002/aoc.3503

  日期：2016.9

  incorporating the features of both bidentate chelating O,O ligand and carbene, shows the maximum catalytic activity. A variety of aryl and heteroaryl methyl and ethyl cinnamates were synthesized using these imidazolium salts as preligands. In addition, NMR studies confirm in situ generation of normal N‐heterocyclic carbenes from the C‐2 position of imidazol‐2‐ylidene ring. The mercury poisoning test was also

  新的不对称N，N的合成，表征及原位催化性能描述了在好氧条件下丙烯酸酯与芳基溴化物在咪唑罗基-赫克偶联过程中基于二氮杂咪唑的二元盐。合成了一系列具有可变的空间和电子特性的柔性二羧酸盐，收率良好。使用光谱技术可以很好地表征所有盐。X射线衍射分析具有相同的双主链和不同的抗衡阴离子的两种盐表明，配体采用两种不同的构象，这些构象受阴离子的性质影响。因此，配体由于其柔性性质而能够根据环境变化而改变其构象。发现所有合成的咪唑鎓盐均在原位具有活性有氧条件下钯催化的米佐罗基-赫克偶联。在这些盐中，结合了双齿螯合O，O配体和卡宾的特征的羟基官能化咪唑鎓盐显示出最大的催化活性。使用这些咪唑鎓盐作为预配体合成了各种肉桂酸的芳基和杂芳基甲基和乙基酯。此外，NMR研究证实原位生成正常N咪唑-2-亚烷基环的C-2位的杂环卡宾。还进行了汞中毒测试，以确定具有催化活性的钯物质的性质。有氧条件，低催化负载量（0.5 mol％
• Regioselective Radical Borylation of α,β-Unsaturated Esters and Related Compounds by Visible Light Irradiation with an Organic Photocatalyst
  作者：Guosong Li、Guanwang Huang、Ruixia Sun、Dennis P. Curran、Wen Dai

  DOI：10.1021/acs.orglett.1c01270

  日期：2021.6.4

  recently been reported and are still rare. Here we describe a photoredox radical hydroboration of α,β-unsaturated esters, amides, ketones, and nitriles with NHC-boranes that uses only an organocatalyst and visible light. The conditions are mild, the substrate scope is broad, and the α/β regioselectivity is high. The reaction requires only the organocatalyst; there is no costly metal, and there are no

  自由基硼氢化反应直到最近才被报道并且仍然很少见。在这里，我们描述了 α,β-不饱和酯、酰胺、酮和腈与 NHC-硼烷的光氧化还原自由基硼氢化反应，该反应仅使用有机催化剂和可见光。条件温和，底物范围广，α/β区域选择性高。该反应只需要有机催化剂；没有昂贵的金属，也没有其他添加剂（碱、助催化剂、引发剂）。
• Palladium catalyst immobilized on functionalized microporous organic polymers for C–C coupling reactions
  作者：Wei Xu、Cijie Liu、Dexuan Xiang、Qionglin Luo、You Shu、Hongwei Lin、Yangjian Hu、Zaixing Zhang、Yuejun Ouyang

  DOI：10.1039/c9ra07303e

  日期：——

  density. Moreover, the immobilized catalyst also had advantages, such as readily available raw materials, chemical and thermal stability, and low synthetic cost. The Pd catalyst is an effective heterogeneous catalyst for carbon–carbon (C–C) coupling reactions, such as the Heck reaction and Suzuki–Miyaura reaction, affording good to high yields. In these reactions, the catalyst was easily recovered and reused

  以苯和1,10-菲咯啉为原料，分别通过Scholl偶联反应和Friedel-Crafts反应制备了两种微孔有机聚合物固定钯（MOP-Pd）催化剂。通过FT-IR、TGA、N 2吸附、SEM、TEM、ICP-AES和XPS对催化剂的结构和组成进行了表征。MOP-Pd 催化剂被发现具有高比表面积、大孔体积和低骨骼密度。此外，固定化催化剂还具有原料易得、化学和热稳定性好、合成成本低等优点。Pd催化剂是一种有效的多相催化剂，适用于碳-碳（C-C）偶联反应，例如Heck反应和Suzuki-Miyaura反应，具有良好的高产率。在这些反应中，催化剂很容易回收并重复使用五次，而没有明显的活性损失。