5-氟-2-(三甲基甲硅烷基)苯基三氟甲磺酸酯 | 1032723-98-0

• 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: 5-氟-2-(三甲基甲硅烷基)苯基三氟甲磺酸酯
• 英文名称: 5-fluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate
• 英文别名: 5-fluoro-2-(trimethylsilyl)phenyl triflate；5-fluoro-2-trimethylsilylphenyl triflate
• CAS: 1032723-98-0
• 化学式: C₁₀H₁₂F₄O₃SSi
• 分子量: 316.349
• InChiKey: BFDLGRPULQYNRO-UHFFFAOYSA-N

物化性质

• 沸点：
  290.3±40.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-氟-2-(三甲基甲硅烷基)苯基三氟甲磺酸酯 、 N-methyl-S,S-diphenylsulfoximine 在 potassium fluoride 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 以68 %的产率得到4-fluoro-N-methyl-N-phenyl-2-(phenylsulfinyl)aniline
  参考文献：
  名称：

  N-烷基亚砜亚胺和芳炔合成邻亚磺酰苯胺

  摘要：

  N -烷基亚砜亚胺与在温和条件下原位生成的芳烃反应，以良好的产率提供邻亚磺酰基苯胺。转化的特点是广泛的底物范围和良好的官能团耐受性。通过单晶X射线衍射确认反应产物的结构。

  DOI：

  10.1021/acs.joc.3c00012

文献信息

• Three-Component Aminoselenation of Arynes
  作者：Rahul N. Gaykar、Avishek Guin、Subrata Bhattacharjee、Akkattu T. Biju

  DOI：10.1021/acs.orglett.9b03789

  日期：2019.12.6

  The three-component coupling of tertiary amines, arynes, and aryl selenium bromide or diaryl diselenide as an electrophilic selenium source allowing the synthesis of 2-selanyl aniline derivatives is reported. This aminoselenation reaction of arynes installs a C-N and C-Se bond under mild conditions, and the products are formed in moderate to good yields. This reaction is compatible with various functional

  据报道，叔胺，芳烃和芳基溴化溴化物或二芳基二硒化物作为亲电子硒源的三组分偶联可以合成2-硒代苯胺衍生物。芳烃的这种氨基硒化反应在温和的条件下安装了CN和C-Se键，并且产物的产率中等至良好。该反应与各种官能团相容，并且还提供了对反应机理的初步研究。
• 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。
• An Umpolung Oxa-[2,3] Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers
  作者：Rahul N. Gaykar、Malini George、Avishek Guin、Subrata Bhattacharjee、Akkattu T. Biju

  DOI：10.1021/acs.orglett.1c00911

  日期：2021.5.7

  An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C═O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic

  据报道涉及芳烃的oxa- [2,3]σ重排以酮为主体，其中的C═O键极性相反。β-酮硫醚和芳烃在原位生成的硫烷基化物经过有效的重排，可以轻松，稳健地合成高官能度的烯醇醚，并具有出色的官能团相容性。初步的机理研究排除了在这种情况下运行Pummerer型重排的可能性。
• Practical Synthesis of Phthalimides and Benzamides by a Multicomponent Reaction Involving Arynes, Isocyanides, and CO₂/H₂O
  作者：Trinadh Kaicharla、Manikandan Thangaraj、Akkattu T. Biju

  DOI：10.1021/ol500403x

  日期：2014.3.21

  Transition-metal-free multicomponent reactions involving arynes and isocyanides with either CO2 or H2O have been reported. With CO2 as the third component, the reactions resulted in the formation of N-substituted phthalimides. The utility of water as the third component furnished benzamide derivatives in moderate to good yields. These reactions took place under mild conditions with broad scope.

  已有报道涉及芳烃和异氰化物与CO 2或H 2 O的无过渡金属的多组分反应。以CO 2为第三组分，反应导致形成N-取代的邻苯二甲酰亚胺。水作为第三组分的用途以中等至良好的产率提供了苯甲酰胺衍生物。这些反应在温和的条件下进行，范围广。
• Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and Aldehydes via Aryl–Aryl Amino Group Migration
  作者：Sachin Suresh Bhojgude、Dnyaneshwar R. Baviskar、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1021/acs.orglett.5b03319

  日期：2015.12.18

  arynes, aromatic tertiary amines, and aldehydes proceeding via the aryl to aryl amino group migration has been demonstrated. This protocol allows rapid access to ortho-functionalized tertiary amines in moderate to good yields. Moreover, activated ketones can also be used as the aldehyde component in the present reaction. The similarity of the aryl–aryl tertiary amino group migration with the Smiles rearrangement

  已证明芳烃，芳族叔胺和醛的无过渡金属多组分偶联是通过芳基向芳基氨基迁移进行的。该方案允许以中等至良好的产率快速获得邻官能化的叔胺。此外，活化的酮也可以用作本反应中的醛组分。芳基-芳基叔氨基迁移与Smiles重排的相似性是惊人的。