(E)-4-(trifluoromethyl)styryl acetate | 1438389-21-9

• 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: (E)-4-(trifluoromethyl)styryl acetate
• 英文别名: [(E)-2-[4-(trifluoromethyl)phenyl]ethenyl] acetate
• CAS: 1438389-21-9
• 化学式: C₁₁H₉F₃O₂
• 分子量: 230.186
• InChiKey: XTHOWBPEZQEYDV-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 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：
  5

反应信息

• 作为产物：
  描述：

  (3E)-4-[4-(三氟甲基)苯基]叔丁基-3-en-2-酮 在 Oxone 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以57%的产率得到(E)-4-(trifluoromethyl)styryl acetate
  参考文献：
  名称：

  General Metal-Free Baeyer–Villiger-Type Synthesis of Vinyl Acetates

  摘要：

  Ozone, a cheap, stable, and nonhazardous oxidizing reagent, transforms alpha,beta-unsaturated ketones of defined stereochemistry into their corresponding vinyl acetates through a Baeyer-Villiger reaction. This process is general and straightforward, tolerating a wide range of functional groups.

  DOI：

  10.1021/ol401143q

文献信息

• An Abnormal N-Heterocyclic Carbene-Based Palladium Dimer: Aqueous Oxidative Heck Coupling Under Ambient Temperature
  作者：Pradip Kumar Hota、Gonela Vijaykumar、Anand Pariyar、Samaresh Chandra Sau、Tamal K. Sen、Swadhin K. Mandal

  DOI：10.1002/adsc.201500220

  日期：2015.10.12

  N-heterocyclic carbene (aNHC)-based ligand and its use in synthesizing an acetate bridged CH activated palladium dimer (1). In complex 1, the carbene ligand displays an abnormal mode of binding with the palladium(II) ion. We used complex 1 as a catalyst for the oxidative Heck coupling reaction of arylboronic acids with electron-deficient as well as electron-rich olefins at ambient temperature in water to produce

  在此我们报告一个新异常N-杂环卡宾（合成一个NHC）类配位体及其在合成的乙酸盐使用桥接CH活化钯二聚物（1）。在配合物1中，卡宾配体显示出与钯（II）离子的异常结合方式。我们使用络合物1作为催化剂，用于在环境温度下于水中进行芳基硼酸与缺电子以及富电子烯烃的氧化Heck偶联反应，从而以良好或优异的收率选择性地生产β-芳基化产物。
• Stereoselective Synthesis of Vinylboronates by Rh‐Catalyzed Borylation of Stereoisomeric Mixtures
  作者：Shenhuan Li、Jie Li、Tianlai Xia、Wanxiang Zhao

  DOI：10.1002/cjoc.201800575

  日期：2019.5

  The stereoselective preparation of vinylboronates via rhodium‐catalyzed borylation of E/Z mixtures of vinyl actetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh‐catalyzed borylation‐isomerization sequence. The

  描述了通过铑催化的乙酸乙烯酯的E / Z混合物的硼酸化硼酸立体选择性地制备乙烯基硼酸酯的方法，该方法还扩展到乙烯基二硼酸酯的合成。这些转变具有高官能团相容性和温和的反应条件。对照实验支持一种涉及Rh催化的硼酸酯化异构化序列的机制。还证明了（Z）-乙烯基硼酸酯的异构化为（E）-异构体。
• Palladium catalysed β-selective oxidative Heck reaction of an electron-rich olefin
  作者：Lingkui Meng、Chao Liu、Wei Zhang、Chao Zhou、Aiwen Lei

  DOI：10.1039/c3cc47045h

  日期：——

  A palladium catalysed oxidative beta-arylation of an electron-rich olefin is described. The reaction was under mild conditions; meanwhile, additives and directing groups are not needed. Various arylboronic acids worked well under the standard conditions.

  描述了富电子烯烃的钯催化的氧化β-芳基化。反应在温和的条件下进行。同时，不需要添加剂和导向基团。各种芳基硼酸在标准条件下效果很好。