2-allyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate | 1423048-78-5

• 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-allyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate
• 英文别名: (2-Prop-2-enyl-6-trimethylsilylphenyl) trifluoromethanesulfonate；(2-prop-2-enyl-6-trimethylsilylphenyl) trifluoromethanesulfonate
• CAS: 1423048-78-5
• 化学式: C₁₃H₁₇F₃O₃SSi
• 分子量: 338.423
• InChiKey: AVQDFQIUXRYUCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-allyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 、 trifluoromethylsilver 在 2,2,6,6-四甲基哌啶 、 (碘乙炔基)苯 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以53%的产率得到1-allyl-2-iodo-3-(trifluoromethyl)benzene
  参考文献：
  名称：

  Silver-Mediated Trifluoromethylation–Iodination of Arynes

  摘要：

  An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF3 has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.

  DOI：

  10.1021/ja312711c
• 作为产物：
  描述：

  三氟甲磺酸酐 、 [2-Bromo-6-(prop-2-en-1-yl)phenoxy]trimethylsilane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以14.58 g的产率得到2-allyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Silver-Mediated Trifluoromethylation–Iodination of Arynes

  摘要：

  An unprecedented silver-mediated vicinal trifluoromethylation-iodination of arynes that quickly introduces CF3 and I groups onto aromatic rings in a single step to give o-trifluoromethyl iodoarenes has been developed. A new reactivity of AgCF3 has been revealed, and 2,2,6,6-tetramethylpiperidine plays an important role in this difunctionalization reaction.

  DOI：

  10.1021/ja312711c

文献信息

• Trifluoromethyl Benzoate: A Versatile Trifluoromethoxylation Reagent
  作者：Min Zhou、Chuanfa Ni、Yuwen Zeng、Jinbo Hu

  DOI：10.1021/jacs.8b04000

  日期：2018.6.6

  Trifluoromethyl benzoate (TFBz) is developed as a new shelf-stable trifluoromethoxylation reagent, which can be easily prepared from inexpensive starting materials using KF as the only fluorine source. The synthetic potency of TFBz is demonstrated by trifluoromethoxylation-halogenation of arynes, nucleophilic substitution of alkyl (pseudo)halides, cross-coupling with aryl stannanes, and asymmetric

  苯甲酸三氟甲酯 (TFBz) 被开发为一种新的货架稳定的三氟甲氧基化试剂，它可以很容易地从廉价的原料中制备，使用 KF 作为唯一的氟源。芳烃的三氟甲氧基化-卤化、烷基（伪）卤化物的亲核取代、与芳基锡烷的交叉偶联和烯烃的不对称双官能化证明了 TFBz 的合成效力。在冠醚络合的钾阳离子的帮助下，芳炔的前所未有的三氟甲氧基化-卤化在室温下顺利进行，这显着稳定了衍生自 TFBz 的三氟甲氧基阴离子。
• Silver-Catalyzed Formal Insertion of Arynes into R_fI Bonds
  作者：Yuwen Zeng、Jinbo Hu

  DOI：10.1002/chem.201402846

  日期：2014.6.2

  An unprecedented silver‐catalyzed formal insertion of arynes into RfI (Rf=CF3, C2F5) bonds has been developed. This protocol provides easy access to various ortho‐perfluoroalkyl iodoarenes under mild conditions. In this insertion reaction, an ionic atom‐transfer reaction of RfI occurs, and a silver‐mediated metathesis process is involved in the efficient transfer of the electropositive iodine atom

  arynes的前所未有的银催化的正式插入ř ˚F  I（R ˚F = CF 3，C 2 ˚F 5）键已被开发。该协议可在温和条件下轻松访问各种邻全氟烷基碘芳烃。在该插入反应中，发生R f I的离子原子转移反应，并且银介导的复分解过程参与了正电碘原子的有效转移。
• <i>S</i> ‐(Trifluoromethyl)Benzothioate (TFBT): A KF‐Based Reagent for Nucleophilic Trifluoromethylthiolation
  作者：Depei Meng、Yichong Lyu、Chuanfa Ni、Min Zhou、Yang Li、Jinbo Hu

  DOI：10.1002/chem.202104395

  日期：2022.3

  developed as an inexpensive, bench-stable and user-friendly trifluoromethylthiolation reagent. TFBT reagent can readily release SCF3− with various counterions. The synthetic application of TFBT is demonstrated by trifluoromethylthiolation-halogenation of arynes, bis(trifluoromethylthiolation)-halogenation of 1,2-benzdiynes, nucleophilic substitution of alkyl halides, deoxytrifluoromethylthiolation of alcohols

  无需 HF：S- (三氟甲基)苯硫代苯甲酸酯 (TFBT) 可通过使用 KF 作为唯一的氟源轻松合成，已被开发为廉价、稳定且用户友好的三氟甲基硫醇化试剂。TFBT 试剂可以很容易地释放 SCF 3 -与各种反离子。TFBT 的合成应用通过芳烃的三氟甲基硫醇化-卤化、1,2-苯二炔的双（三氟甲基硫醇化）-卤化、卤代烷的亲核取代、醇的脱氧三氟甲基硫醇化以及与芳基和乙烯基硼酸的交叉偶联来证明。
• Copper-Mediated Trifluoromethylation–Allylation of Arynes
  作者：Xinkan Yang、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.8b00101

  日期：2018.2.16

  An unprecedented three-component copper-mediated vicinal trifluoromethylation–allylation of arynes is described. A wide range of structurally diverse trifluoromethylated allylarenes can be quickly assembled in one step. The application of the method has been demonstrated in the expedient synthesis of the CF3-containing analogue of the antispasmodic drug papaverine. The new reactivity of the [CuCF3]

  描述了史无前例的三组分铜介导的邻位三氟甲基化-芳烃的烯丙基化。一步就可以快速组装多种结构多样的三氟甲基化烯丙基芳烃。该方法的应用已在合成抗痉挛药物罂粟碱的含CF 3的类似物中得到证明。由廉价的工业副产物氟仿生成的[CuCF 3 ]试剂具有新的优势，具有独特的优势。
• Silver-Mediated Trifluoromethylthiolation–Iodination of Arynes
  作者：Yuwen Zeng、Jinbo Hu

  DOI：10.1021/acs.orglett.6b00142

  日期：2016.2.19

  A one-pot trifluoromethylthiolation–iodination of arynes with trifluoromethylthiosilver (AgSCF3) and 1-iodophenylacetylene is described. This protocol allows rapid construction of o-trifluoromethylthiolated arene building blocks in moderate yields. These products were found to be excellent precursors for Yagupolskii–Umemoto-type electrophilic trifluoromethylation reagents.

  描述了用三氟甲基硫代银（AgSCF 3）和1-碘苯基乙炔对芳烃进行的一锅三氟甲基硫基化碘化反应。该方案允许以中等收率快速构建邻-三氟甲基硫醇化的芳烃结构单元。发现这些产品是Yagupolskii–Umemoto型亲电子三氟甲基化试剂的出色前体。