乙基3-[3-(三氟甲基)苯基]-2-丙炔酸酯 | 58686-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙基3-[3-(三氟甲基)苯基]-2-丙炔酸酯
• 英文名称: ethyl 3-(3-(trifluoromethyl)phenyl)propiolate
• 英文别名: ethyl 3-trifluoromethylphenylpropiolate；Ethyl 3-[3-(trifluoromethyl)phenyl]prop-2-ynoate
• CAS: 58686-69-4
• 化学式: C₁₂H₉F₃O₂
• 分子量: 242.197
• InChiKey: PFSQMVYWLYJUMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  278.6±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基3-[3-(三氟甲基)苯基]-2-丙炔酸酯 在 silver hexafluoroantimonate 、 C₂₇H₃₆AuClN₂⁽¹⁺⁾ 、 丙酮 作用下， 反应 9.0h， 以92%的产率得到(3-三氟甲基苯甲酰)乙酸乙酯
  参考文献：
  名称：

  使用阳离子 NHC-AuIC 催化剂通过炔基酯和炔基酮的区域选择性水合有效合成功能化 β-酮酯和 β-二酮

  摘要：

  通过使用阳离子 NHC-AuI 催化剂，α-炔基酯和酮的区域选择性水合分别产生 β-酮酯和 β-二酮。在反应条件下通过羟醛自缩合控制丙酮中水的释放使得丙酮成为比 1,4-二恶烷/水更好的溶剂，用于水合具有敏感酯部分的 α-炔基酯。

  DOI：

  10.1002/ejoc.201601025
• 作为产物：
  描述：

  3-(三氟甲基)苯硼酸 、 丙炔酸乙酯 在 copper(l) iodide 、 air 、 caesium carbonate 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以75%的产率得到乙基3-[3-(三氟甲基)苯基]-2-丙炔酸酯
  参考文献：
  名称：

  Ligand-free copper(Ι)-catalyzed Sonogashira-type coupling of arylboronic acids with terminal alkynes

  摘要：

  An efficient ligand-free Cul-catalyzed Sonogashira-type coupling reaction of arylboronic acids with terminal alkynes under air is described. The electron-deficient alkynes gave the desired cross-coupling products in good yields. Thus, it represents a simple and alternative method for the traditional Sonogashira reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.093

文献信息

• Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3-azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes
  作者：Robin Durham、Jérémie Mandel、Nicolas Blanchard、William Tam

  DOI：10.1139/v11-135

  日期：2011.12

  Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3-azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes were investigated. Yields of up to 90% were obtained though regioselectivity was modest. Select cycloadducts could be separated and used to access a highly functionalized [3.2.0] bicyclic structure through reductive cleavage of the N–O bond. These ring-opened products displayed a chemical exchange phenomenon in 1D carbon NMR and required characterization by 2D NMR techniques.

  钌催化的2-氧-3-氮杂双环[2.2.1]庚-5-烯与非对称炔烃的[2+2]环加成反应进行了研究。尽管区域选择性较低，但产率高达90%。可分离选择性环加成产物，并通过还原性断裂N-O键来获得高度官能化的[3.2.0]双环结构。这些环开放产物在1D碳核磁共振中显示了化学交换现象，并需要通过2D核磁共振技术进行表征。
• Zinc-mediated CH-activation of tetrahydrofuran under mild conditions for the regioselective addition to aryl-propiolates
  作者：Florian Pünner、Gerhard Hilt

  DOI：10.1039/c4cc03348e

  日期：——

  The CH-activation of THF is realized in a zinc-mediated process using a dibromocyclopropane as a crucial additive. The highly regioselective addition to aryl-substituted propiolates as well as the regio- and stereoselective addition to diynes are described.

  THF 的 CH 活化是在锌介导的过程中使用二溴环丙烷作为关键添加剂实现的。描述了芳基取代的丙炔酸酯的高度区域选择性加成以及二炔的区域和立体选择性加成。
• Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from <i>N</i>-Propargyl Enamines/Amides
  作者：Mrinmay Baidya、Jhilik Dutta、Suman De Sarkar

  DOI：10.1021/acs.orglett.3c01355

  日期：2023.5.26

  Intramolecular electro-oxidative addition of enamines or amides to nonactivated alkynes was attained to access carbonyl-pyrroles or -oxazoles from N-propargyl derivatives. Organoselenium was employed as the electrocatalyst, which played a crucial role as a π-Lewis acid and selectively activated the alkyne for the successful nucleophilic addition. The synthetic strategy permits a wide range of substrate

  实现了烯胺或酰胺对未活化炔烃的分子内电氧化加成，以从N-炔丙基衍生物中获得羰基-吡咯或-恶唑。有机硒被用作电催化剂，它作为π-路易斯酸起着至关重要的作用，并选择性地激活炔烃以成功进行亲核加成。合成策略允许广泛的底物范围，产率高达 93%。几个机械实验，包括硒结合的中间加合物的分离，启发了电催化途径。
• Ligand-free copper(Ι)-catalyzed Sonogashira-type coupling of arylboronic acids with terminal alkynes
  作者：Changduo Pan、Fang Luo、Wenhui Wang、Zhishi Ye、Jiang Cheng

  DOI：10.1016/j.tetlet.2009.06.093

  日期：2009.9

  An efficient ligand-free Cul-catalyzed Sonogashira-type coupling reaction of arylboronic acids with terminal alkynes under air is described. The electron-deficient alkynes gave the desired cross-coupling products in good yields. Thus, it represents a simple and alternative method for the traditional Sonogashira reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of Functionalized β-Keto Esters and β-Diketones through Regioselective Hydration of Alkynyl Esters and Alkynyl Ketones by Use of a Cationic NHC-Au^ICatalyst
  作者：Chandrahas Tarigopula、Ganesh Kumar Thota、Rengarajan Balamurugan

  DOI：10.1002/ejoc.201601025

  日期：2016.12

  Regioselective hydration of α-alkynyl esters and ketones by using a cationic NHC–AuI catalyst results in β-keto esters and β-diketones, respectively. Controlled release of water in acetone by aldol self-condensation under the reaction conditions makes acetone as better solvent than 1,4-dioxane/water for the hydration of α-alkynyl esters having sensitive ester moieties.

  通过使用阳离子 NHC-AuI 催化剂，α-炔基酯和酮的区域选择性水合分别产生 β-酮酯和 β-二酮。在反应条件下通过羟醛自缩合控制丙酮中水的释放使得丙酮成为比 1,4-二恶烷/水更好的溶剂，用于水合具有敏感酯部分的 α-炔基酯。