(Z)-ethyl 3-(4-fluorophenyl)acrylate | 136265-10-6

• 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: (Z)-ethyl 3-(4-fluorophenyl)acrylate
• 英文别名: ethyl (Z)-3-(4-fluorophenyl)acrylate；ethyl (Z)-3-(4-fluorophenyl)prop-2-enoate
• CAS: 136265-10-6
• 化学式: C₁₁H₁₁FO₂
• 分子量: 194.206
• InChiKey: UNAXNPTZJKKUGO-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 3-(4-fluorophenyl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到(Z)-3-(4-fluorophenyl)acrylic acid
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013
• 作为产物：
  描述：

  丙炔酸乙酯 在 四(三苯基膦)钯 、 正丁基锂 、 三丁基膦 、 水 、 二异丙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 5.5h， 生成 (Z)-ethyl 3-(4-fluorophenyl)acrylate
  参考文献：
  名称：

  Z-选择性膦在水的存在下促进 ynoates 和 propynic amides 的 1,4-还原

  摘要：

  在水存在下，膦介导的取代丙炔酸酯和酰胺的还原产生了具有高Z选择性的部分还原的 α,β-不饱和酯和酰胺。在某些情况下，产物的竞争性原位 Z对E异构化降低了分离的 α,β-不饱和羰基产物的Z对E比。反应时间和反应混合物中的磷化氢和水的量是通过防止或降低Z - 至E -产物异构化速率来控制选择性的关键实验因素。密切的反应监测可以隔离Z-具有高选择性的烯烃。计算结果表明，由于EP -羟基正膦中间体的立体选择性形成，反应可能是高度Z选择性的。

  DOI：

  10.1039/d1ob00909e

文献信息

• One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
  作者：Xiaochun Yu、Shun Wang、Weijie Ding、Juan Hu、Huile Jin

  DOI：10.1055/s-0036-1590904

  日期：2018.1

  reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields. A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O2 in air as oxidant. The solvent mixture of acetonitrile

  摘要 通过在空气中以O 2为氧化剂的一锅铜催化氧化成功地实现了合成α，β-不饱和酯，酮和腈的通用方法。乙腈和甲酰胺（1：1）的溶剂混合物经过优化，可确保在一锅中有效地进行醇类的氧化，de盐的去质子化和Wittig反应。已针对该方法探索了广泛的底物，包括三个吸电子基团（CO 2 Et，COPh，CN）官能化的salts盐。它们不仅与苄基和杂芳族醇反应，而且与脂族醇反应，以中等至极好的收率形成相应的α，β-不饱和酯，酮和腈。 通过在空气中以O 2为氧化剂的一锅铜催化氧化成功地实现了合成α，β-不饱和酯，酮和腈的通用方法。乙腈和甲酰胺（1：1）的溶剂混合物经过优化，可确保在一锅中有效地进行醇类的氧化，de盐的去质子化和Wittig反应。已针对该方法探索了广泛的底物，包括三个吸电子基团（CO 2 Et，COPh，CN）官能化的salts盐。它们不仅与苄基和杂芳族醇反应，而且与脂族醇反应，以中等至极
• Oxime ligands for Pd catalysis of the Mizoroki–Heck reaction, Suzuki–Miyaura coupling & annulation reactions
  作者：Pronnoy G. Bangar、Pradip D. Nahide、Heena K. Meroliya、Shobha A. Waghmode、Suresh Iyer

  DOI：10.1080/00397911.2020.1826969

  日期：2021.1.17

  Monodentate and bidentate chelating oximes are readily available ligands for the Pd catalysis of the Mizoroki–Heck reaction and the Suzuki coupling. High yields were obtained in the Suzuki coupling...

  单齿和双齿螯合肟是用于 Pd 催化 Mizoroki-Heck 反应和 Suzuki 偶联的现成配体。在 Suzuki 联轴器中获得了高产量...
• Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction
  作者：Cheng Ren、Zhenyu Shi、Weijie Ding、Zhiqing Liu、Huile Jin、Xiaochun Yu、Shun Wang

  DOI：10.1016/j.tetlet.2017.09.020

  日期：2018.1

  An efficient one-pot synthesis of α, β-unsaturated esters through the aerobic oxidation – Wittig tandem reaction of alcohols and phosphorous ylide is developed. This new method operates under mild reaction conditions, and uses CuI/TEMPO (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) as co-catalyst and air (O2) as the oxidant. It tolerates a wide range of functionalized benzylic alcohol and aliphatic

  开发了一种有效的一锅法合成α，β-不饱和酯的方法，即通过醇与磷的叶立德的好氧氧化-Wittig串联反应。该新方法在温和的反应条件下运行，并使用CuI / TEMPO（TEMPO = 2,2,6,6-四甲基哌啶-N-氧基）作为助催化剂，并使用空气（O 2）作为氧化剂。它可以耐受各种官能化的苯甲醇和脂肪醇。
• Chromatography-Free Wittig Reactions Using a Bifunctional Polymeric Reagent
  作者：Peter Shu-Wai Leung、Yan Teng、Patrick H. Toy

  DOI：10.1021/ol1021614

  日期：2010.11.5

  The first example of a polystyrene bearing two distinct reagent groups has been prepared. This phosphine and amine functionalized material was used in one-pot Wittig reactions with an aldehyde and either an α-halo-ester, -ketone, or -amide. Due to the heterogeneous nature of the polymer, the desired alkene product of these reactions could be isolated in excellent yield in essentially pure form after

  已经制备了带有两个不同试剂基团的聚苯乙烯的第一个例子。该膦和胺官能化的材料用于与醛和α-卤代酯，-酮或-酰胺的一锅法Wittig反应中。由于聚合物的非均质性质，仅在过滤和除去溶剂后，就可以以优异的收率以基本纯净的形式分离出这些反应的所需烯烃产物。
• Copper-catalyzed Oxidative Olefination of Thiols Using Sulfones and Phosphorous Ylides
  作者：Pranab K. Shyam、Chan Lee、Hye-Young Jang

  DOI：10.1002/bkcs.10347

  日期：2015.7

  Copper‐catalyzed one‐pot conversion of thiols to olefins was conducted under aerobic conditions. Thiols were oxidized to generate thioaldehydes, which reacted with sulfones or phosphorous ylides to form the corresponding olefins. The formation of thiosulfonates and phosphorous sulfides confirms that these olefination protocols proceed via thioaldehyde‐sulfone and thioaldehyde‐ylide adducts.

  铜催化的一锅法硫醇向烯烃的转化在好氧条件下进行。硫醇被氧化生成硫代醛，该硫代醛与砜或磷酰化物反应形成相应的烯烃。硫代磺酸盐和硫化磷的形成证实了这些烯化方案是通过硫醛-砜和硫醛-内酯加合物进行的。