ethyl 3-fluoro-3-phenylpropanoate | 70199-99-4

• 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: ethyl 3-fluoro-3-phenylpropanoate
• CAS: 70199-99-4
• 化学式: C₁₁H₁₃FO₂
• 分子量: 196.221
• InChiKey: BCLAZJYJFNWGQF-UHFFFAOYSA-N

物化性质

• 沸点：
  132.5-134 °C(Press: 24 Torr)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯丙酸乙酯 在 占吨酮 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 0.47h， 以81%的产率得到ethyl 3-fluoro-3-phenylpropanoate
  参考文献：
  名称：

  A Continuous-Flow Protocol for Light-Induced Benzylic Fluorinations

  摘要：

  A continuous-flow protocol for the light-induced fluorination of benzylic compounds is presented. The procedure uses Selectfluor as the fluorine source and xanthone as an inexpensive and commercially available photoorganocatalyst. The flow photoreactor is based on transparent fluorinated ethylene propylene tubing and a household compact fluorescent lamp. The combination of xanthone with black-light irradiation results in very efficient fluorination. Good to excellent isolated yields were obtained for a variety of substrates bearing different functional groups applying residence times below 30 min.

  DOI：

  10.1021/jo5016757

文献信息

• A metal-free and regioselective approach to (Z)-β-fluorovinyl sulfones and their chemoselective hydrogenation to β-fluoroalkyl sulfones
  作者：Daniel M. Sedgwick、Raquel Román、Pablo Barrio、Cristina Morales、Santos Fustero

  DOI：10.1016/j.jfluchem.2017.12.016

  日期：2018.2

  metal-free hydrofluorination reaction of alkynyl sulfones was developed using TBAF—one of the cheapest and most commonly available fluoride sources. In addition, the reactivity of the resulting β-fluorovinyl sulfones was studied, focusing on their selective hydrogenation reaction. Both β-fluorovinyl sulfones and their hydrogenation products β-fluoroalkyl sulfones may find applications in medicinal and agrochemical

  使用TBAF开发了一种高度区域选择性，无金属的炔基砜氢氟化反应，TBAF是最便宜，最常用的氟化物来源之一。另外，研究了所得β-氟乙烯基砜的反应性，着眼于它们的选择性氢化反应。β-氟乙烯砜及其加氢产物β-氟烷基砜均可在医学和农业化学领域找到应用。
• Silver-Catalyzed Decarboxylative Alkylfluorination of Alkenes
  作者：Chen-Guang Li、Qiang Xie、Xiao-Lan Xu、Feng Wang、Bei Huang、Yu-Feng Liang、Hua-Jian Xu

  DOI：10.1021/acs.orglett.9b03381

  日期：2019.10.18

  with the catalysis of silver(I) and Selectfluor as both the oxidant and fluorine source. This reaction is highly chemoselective, producing the decarboxylative alkylfluorination products rather than the competitive fluorination of aliphatic carboxylic acids. This practical transformation proceeds efficiently in aqueous media at room temperature and exhibits a large range of functional-group tolerance

  以银（I）和Selectfluor作为氧化剂和氟源的催化作用，开发了用于烷基烯烃氟化的烷基羧酸脱羧剂。该反应是高度化学选择性的，产生脱羧烷基氟化产物，而不是脂肪族羧酸的竞争性氟化。这种实际的转变在室温下在水性介质中有效地进行，并且在各种伯和仲脂肪族羧酸盐和烯烃中表现出大范围的官能团耐受性。
• Enantioselective Palladium-Catalyzed Oxidative β,β-Fluoroarylation of α,β-Unsaturated Carbonyl Derivatives
  作者：Javier Miró、Carlos del Pozo、F. Dean Toste、Santos Fustero

  DOI：10.1002/anie.201603046

  日期：2016.7.25

  The site‐selective palladium‐catalyzed three‐component coupling of deactivated alkenes, arylboronic acids, and N‐fluorobenzenesulfonimide is disclosed herein. The developed methodology establishes a general, modular, and step‐economical approach to the stereoselective β‐fluorination of α,β‐unsaturated systems.

  本文公开了失活烯烃，芳基硼酸和N-氟苯磺酰亚胺的选择性钯催化三组分偶联。发达的方法论为α，β-不饱和系统的立体选择性β-氟化建立了通用，模块化，经济的方法。
• Palladium-Catalyzed Electrooxidative Hydrofluorination of Aryl-Substituted Alkenes with a Nucleophilic Fluorine Source
  作者：Anup Mandal、Jieun Jang、Baeho Yang、Hyunwoo Kim、Kwangmin Shin

  DOI：10.1021/acs.orglett.2c04045

  日期：2023.1.13

  Herein, we report an electrocatalytic hydrofluorination of aryl-substituted alkenes with a nucleophilic fluorine source. The merger of palladium catalysis with electrooxidation enables the transformation of various substrates ranging from styrenes to more challenging α,β-unsaturated carbonyl derivatives to the corresponding benzylic fluorides. This method can also be applied to the late-stage modification

  在此，我们报道了芳基取代烯烃与亲核氟源的电催化氢氟化反应。钯催化与电氧化的结合能够将各种底物从苯乙烯转化为更具挑战性的 α,β-不饱和羰基衍生物，再转化为相应的苄基氟化物。该方法也可应用于药物衍生物的后期修饰。机理研究表明，通过阳极氧化生成高价钯中间体是这种电催化氢氟化反应的关键步骤。
• Effet de la concentration en acide fluorhydrique dans la pyridine sur la regio-selective de la fluoration par deamination d′α-amino-esters : syntheses de composes cargoxyles-β-fluores.
  作者：Sylvain Hamman、Claude G. Beguin

  DOI：10.1016/s0040-4039(00)81326-x

  日期：1983.1