2-methoxy-2-oxo-1-phenylethyl 4-fluorobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-2-oxo-1-phenylethyl 4-fluorobenzoate
• 英文别名: (2-Methoxy-2-oxo-1-phenylethyl) 4-fluorobenzoate；(2-methoxy-2-oxo-1-phenylethyl) 4-fluorobenzoate
• 化学式: C₁₆H₁₃FO₄
• 分子量: 288.275
• InChiKey: BHJCGLBCAMFTGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 在 正丁基锂 、 三(五氟苯基)硼烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.25h， 生成 2-methoxy-2-oxo-1-phenylethyl 4-fluorobenzoate
  参考文献：
  名称：

  三芳基硼烷催化芳基酯与重氮化合物的烯基化反应。

  摘要：

  在此，我们报告了一种在没有过渡金属催化剂的情况下形成碳-碳键的简便、温和的反应方案。我们演示了芳基酯与 α-重氮酯的无金属烯基化反应，得到高度官能化的烯炔产物。使用催化量的三（五氟苯基）硼烷（10-20 mol%）以良好到优异的收率（36-87%）提供C=C偶联产物（31个示例）。DFT 研究用于阐明这种烯基化反应的机制。

  DOI：

  10.1002/anie.202007176

文献信息

• A Phosphetane Catalyzes Deoxygenative Condensation of α-Keto Esters and Carboxylic Acids via P^III/P^V═O Redox Cycling
  作者：Wei Zhao、Patrick K. Yan、Alexander T. Radosevich

  DOI：10.1021/ja511889y

  日期：2015.1.21

  A small-ring phosphacycle is found to catalyze the deoxygenative condensation of α-keto esters and carboxylic acids. The reaction provides a chemoselective catalytic synthesis of α-acyloxy ester products with good functional group compatibility. Based on both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic P(III)/P(V)═O cycling. The importance

  发现小环磷酸环可催化 α-酮酯和羧酸的脱氧缩合。该反应提供了具有良好官能团相容性的α-酰氧基酯产物的化学选择性催化合成。基于化学计量和催化机理实验，建议反应通过催化 P(III)/P(V)=O 循环进行。观察到的温度依赖性产物选择性效应证实了环应变在磷环催化剂中的重要性。结果表明，与路易斯碱（亲核）催化相反，通过 P(III)/P(V)=O 氧化还原循环操作的有机磷基催化剂的设计标准存在固有差异。
• Tropylium-Catalyzed O–H Insertion Reactions of Diazoalkanes with Carboxylic Acids
  作者：Claire Empel、Thanh Vinh Nguyen、Rene M. Koenigs

  DOI：10.1021/acs.orglett.0c04069

  日期：2021.1.15

  describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O–H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).

  在本文中，我们描述了一种非苯环芳族碳正离子，即对苯二酚，在重氮烷与苯甲酸的O–H官能化反应中作为有机路易斯酸催化剂的应用。新开发的协议以优异的效率（43个示例，产率高达99％）适用于各种重氮烷烃和羧酸底物。
• Hydroacylation of Activated Ketones Catalyzed by <i>N</i>-Heterocyclic Carbenes
  作者：Audrey Chan、Karl A. Scheidt

  DOI：10.1021/ja060833a

  日期：2006.4.1

  N-heterocyclic carbenes derived from triazolium salts are effective catalysts between 10 and 15 mol % for the hydroacylation of activated ketones. The reducing equivalent is generated via the interaction of a nucleophilic carbene species and an aromatic aldehyde. The subsequent alcohol product can undergo an acylation event with the resulting acyl heteroazolium intermediate formed in situ between the NHC and the aldehyde. This unprecedented multiple bond-forming reaction can accommodate aromatic aldehydes as the hydride source and various electron-deficient ketones. Preliminary mechanistic evidence indicates that the reduction and acylation steps are sequential operations. The intramolecular variant of this organocatalytic reaction affords benzofuranones in good yield.
• Carboxylic Acid Functionalization Using Sulfoxonium Ylides as a Carbene Source
  作者：Fathima Febin Koothradan、Anusree Suresh Babu、Krishnendu P. Pushpakaran、Arumugam Jayarani、Chinnappan Sivasankar

  DOI：10.1021/acs.joc.1c02632

  日期：2022.8.19
• Triarylborane‐Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds
  作者：Ayan Dasgupta、Katarína Stefkova、Rasool Babaahmadi、Lukas Gierlichs、Alireza Ariafard、Rebecca L. Melen

  DOI：10.1002/anie.202007176

  日期：2020.9

  Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal‐free alkenylation reactions of aryl esters with α‐diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent

  在此，我们报告了一种在没有过渡金属催化剂的情况下形成碳-碳键的简便、温和的反应方案。我们演示了芳基酯与 α-重氮酯的无金属烯基化反应，得到高度官能化的烯炔产物。使用催化量的三（五氟苯基）硼烷（10-20 mol%）以良好到优异的收率（36-87%）提供C=C偶联产物（31个示例）。DFT 研究用于阐明这种烯基化反应的机制。