1,2-双(4-(三氟甲基)苯基)乙烯 | 1002717-44-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,2-双(4-(三氟甲基)苯基)乙烯
• 英文名称: 1,2-bis(p-trifluoromethylphenyl)ethylene
• 英文别名: 1,2-bis(4-(trifluoromethyl)phenyl)ethene；(E)-1,2-Bis[4-(trifluoromethyl)phenyl]ethene；1-(trifluoromethyl)-4-[2-[4-(trifluoromethyl)phenyl]ethenyl]benzene
• CAS: 1002717-44-3
• 化学式: C₁₆H₁₀F₆
• 分子量: 316.246
• InChiKey: AKPPHKDAEYUZPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-双(4-(三氟甲基)苯基)乙烯 在 lithium perchlorate 作用下， 以 水 、 乙腈 为溶剂， 反应 17.0h， 以96%的产率得到对三氟甲基苯甲醛
  参考文献：
  名称：

  Electrocatalytic Oxidative Cleavage of Electron-Deficient Substituted Stilbenes in Acetonitrile−Water Employing a New High Oxidation Potential Electrocatalyst. An Electrochemical Equivalent of Ozonolysis

  摘要：

  A series of symmetrical and unsymmetrical stilbenes bearing two or more strong electron-withdrawing groups were oxidatively cleaved to the corresponding aldehydes in high yield by electrocatalytic anodic oxidation in aqueous acetonitrile employing a new high oxidation potential triphenylamine electrocatalyst. The oxidations apparently involve the corresponding 1,2-diols, which are also converted to aldehydes in high yield under the same conditions.

  DOI：

  10.1021/ol7026416
• 作为产物：
  描述：

  2,5-二甲基-2,4-己二烯 、 对三氟甲基苯乙烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以34%的产率得到1-(2-methylprop-1-en-1-yl)-4-(trifluoromethyl)benzene
  参考文献：
  名称：

  Alkene Cross‐Metathesis with 2,5‐Dimethyl‐2,4‐Hexadiene Enables Isobutylenyl/Prenyl Functionalizations and Rubber Valorization

  摘要：

  2,5‐Dimethyl‐2,4‐hexadiene is a readily available and easily managable compound, whose symmetric and polymethylated dienic structure should be prone to engage in cross‐metathesis reactions with other alkenes, but this has not been apparently exploited so far. Here we show that this reactant enables the easy synthesis of tri‐ and tetra‐susbtituted alkenes (i. e. isobutylenyl and prenyl groups) from simple alkenes under mild reaction conditions, not only with the conventional 2nd generation Grubbs catalyst but also with other Grela‐type catalyts such as StickyCat,TM AquaMetTM and GreenCatTM. The use of liquid and low volatile 2,5‐dimethyl‐2,4‐hexadiene avoids the use of gaseous alkene reactants and, besides, showcases the reactivity of polyisoprene (rubber), thus allowing to optimize the reaction conditions for rubber upcycling, after metathesis reaction of the pristine or used polymer with simple alkenes. These results bring low volatile isoprene‐type compounds as privileged poly‐substituted reactants for alkene cross‐metathesis reactions.

  DOI：

  10.1002/chem.202400860

文献信息

• B( <scp> C ₆ F ₅ </scp> ) <scp> ₃ ‐Catalyzed </scp> Hydroboration of Alkenes with <scp> <i>N</i> ‐Heterocyclic </scp> Carbene Boranes <i>via</i> B—H Bond Activation
  作者：Qiaotian Wang、Wei Meng、Xiangqing Feng、Haifeng Du

  DOI：10.1002/cjoc.202000489

  日期：2021.4

  Significantly, excellent regioselectivities were obtained in some cases. Mechanistic studies indicate that the B—H bond cleavage is likely involved in the rate‐determining step. In addition, an electrophilic addition of NHC‐borenium cation to alkenes and the subsequent formation of carbocation are also postulated. The current work provides a promising method for the activation of stable borane adducts

  在这项工作中，开发了一种新的活化N-杂环卡宾硼烷（NHC-硼烷）的方式，该方式是通过以沮丧的Lewis对方式通过路易斯酸B（C 6 F 5）3氢化物提取生成高反应性的两性离子物质。B（C 6 F 5）3的合适底物包括苯乙烯，β-甲基苯乙烯，苯乙烯和烷基烯烃等多种烯烃。催化硼氢化以高至高收率提供所需的产品。显着地，在某些情况下获得了优异的区域选择性。机理研究表明，在确定速率的步骤中可能涉及到B键的断裂。此外，还假定将NHC-硼阳离子亲电加成到烯烃中，并随后形成碳正离子。目前的工作为稳定硼烷加合物的活化提供了一种有前途的方法，这可能在将来引起一些有趣的转变。
• 一种硼酸酯化合物的制备方法
  申请人：中国科学院化学研究所

  公开号：CN111718363B

  公开（公告）日：2021-07-13

  本发明公开一种式I所示硼酸酯化合物的制备方法。该方法包括下述步骤：在催化剂存在的条件下，使式II所示的化合物与式III所示的氮杂卡宾硼烷进行烯烃硼氢化反应即得。本发明利用二苯基乙烯与氮杂卡宾硼烷在催化剂存在的条件下，在溶液中进行反应，实现了硼酸酯化合物的合成。
• Flavin-Mediated Photocatalysis Provides a General Platform for Sulfide C–H Functionalization
  作者：Alex S. Anderton、Oliver J. Knowles、James A. Rossi-Ashton、David J. Procter

  DOI：10.1021/acscatal.3c05785

  日期：2024.2.16

  Functionalized sulfides are important in many areas of science, ranging from chemical biology through drug discovery to organic materials chemistry. Sulfides bearing pendant reactive groups in the α-position are particularly useful; however, methods for the selective valorization of simple sulfides or the late-stage functionalization of complex sulfides by the convenient addition of valuable functionality

  功能化硫化物在许多科学领域都很重要，从化学生物学到药物发现再到有机材料化学。在 α 位带有反应性侧基的硫化物特别有用；然而，选择性增值简单硫化物或通过方便添加有价值的官能团对复杂硫化物进行后期功能化的方法尚未得到充分探索。在这里，我们通过展示 α-硫 C-H 官能化的三种模式来举例说明硫醚官能化的通用反应平台；氰化、烯基化和炔基化。使用廉价且市售的核黄素四乙酸酯和可见光，可以以良好的产率和高选择性对原料和复合硫化物进行修饰。含蛋氨酸的肽也可以选择性地功能化，并且使用氨基酸掺杂剂的耐受性筛选表明该平台与大多数氨基酸侧链相容，因此是生物共轭的潜在工具。
• A structure–activity relationship study on the Wacker oxidation of stilbenes at ambient condition
  作者：Hossein Reza Darabi、Mohsen Mirzakhani、Kioumars Aghapoor、Khosrow Jadidi、Laleh Faraji、Nader sakhaee

  DOI：10.1016/j.jorganchem.2013.05.008

  日期：2013.9

  To evaluate which structural elements of the stilbenes are responsible for their activity on the Wacker oxidation, a series of stilbenes with various functional moieties and substitution patterns were considered. In this regard, it is found that the oxidation rate of stilbenes strongly depends on their structures to give the corresponding carbonyl compounds. Consequently, the ortho position of alkene and methoxy groups plays a key role in the complexation with PdCl2. The oxidation process is clean with high selectivity of product and low percentage of byproducts. (C) 2013 Elsevier B. V. All rights reserved.