potassium trifluoro(tert-pentyl)borate | 237741-27-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: potassium trifluoro(tert-pentyl)borate
• 英文别名: Potassium trifluoro(2-methylbutan-2-yl)boranuide；potassium;trifluoro(2-methylbutan-2-yl)boranuide
• CAS: 237741-27-4
• 化学式: C₅H₁₁BF₃*K
• mdl: MFCD09992901
• 分子量: 178.047
• InChiKey: LLVJXOVWFKFZBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲基喹啉 、 potassium trifluoro(tert-pentyl)borate 在 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 N,N,N,N-tetraethylammonium tetrafluoroborate 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 以63%的产率得到4-methyl-2-(tert-pentyl)quinoline
  参考文献：
  名称：

  杂芳烃与有机三氟硼酸酯的光电化学CH烷基化

  摘要：

  已经开发了一种用有机三氟硼酸盐进行杂芳烃的CH烷基化的光电化学方法。电催化和光氧化还原催化的合并为有机三氟硼酸盐的烷基自由基的产生和功能化提供了一种无化学氧化剂的方法。使用具有出色的区域选择性和化学选择性的伯，仲和叔烷基三氟硼酸酯对各种杂芳烃进行功能化。

  DOI：

  10.1002/anie.201814488
• 作为产物：
  描述：

  potassium hydrogen difluoride 、 4,4,5,5-tetramethyl-2-(tert-pentyl)-1,3,2-dioxaborolane 以 甲醇 、 水 为溶剂， 反应 2.0h， 以40%的产率得到potassium trifluoro(tert-pentyl)borate
  参考文献：
  名称：

  杂芳烃与有机三氟硼酸酯的光电化学CH烷基化

  摘要：

  已经开发了一种用有机三氟硼酸盐进行杂芳烃的CH烷基化的光电化学方法。电催化和光氧化还原催化的合并为有机三氟硼酸盐的烷基自由基的产生和功能化提供了一种无化学氧化剂的方法。使用具有出色的区域选择性和化学选择性的伯，仲和叔烷基三氟硼酸酯对各种杂芳烃进行功能化。

  DOI：

  10.1002/anie.201814488

文献信息

• Stereoselective Three-Component Allylic Alkylation Enabled by Dual Photoredox/Ni Catalysis
  作者：Qian Zeng、Fengyun Gao、Jordi Benet-Buchholz、Arjan W. Kleij

  DOI：10.1021/acscatal.3c01686

  日期：2023.6.2

  modular and practical approach has been developed for the stereoselective formation of elaborate allylic alcohols through a three-component reaction (3CR) between vinyl cyclic carbonates, olefins, and various radical precursors using dual photoredox/Ni catalysis. The developed process expands the potential of radical-based allylic alkylation to multicomponent approaches under high regio- and stereocontrol

  已经开发了一种模块化和实用的方法，通过使用双重光氧化还原/镍催化在乙烯基环状碳酸酯、烯烃和各种自由基前体之间进行三组分反应 (3CR) 来立体选择性地形成精细的烯丙醇。开发的工艺将基于自由基的烯丙基烷基化的潜力扩展到在高区域和立体控制下的多组分方法，具有大量的个体试剂变化，并提供了获得具有空间拥挤和功能化季碳中心的化合物的途径。催化方案可以扩展到其他烯丙基前体，并且通过简单地改变光催化剂就可以逆转立体选择性。
• Modular construction of <i>N</i>-arylated amino acid esters enabled by a photoredox-catalyzed multicomponent reaction
  作者：Qing Li、Hanhan Sun、Fengying Yan、Yuanyuan Zhao、Yicheng Zhang、Chao Zhou、Man-yi Han、Hongji Li、Xianwei Sui

  DOI：10.1039/d3gc01633a

  日期：——

  An efficient photoredox-catalyzed three-component coupling reaction of aryl amine, glyoxalate and alkyltrifluoroborates has been reported. A variety of N-arylated amino esters were constructed rapidly using an organic photocatalyst under mild conditions. Broad substrate scope and good functional group tolerance are the key features of this strategy.

  据报道，芳基胺、乙醛酸酯和烷基三氟硼酸酯的高效光氧化还原催化三组分偶联反应。使用有机光催化剂在温和条件下快速构建了多种N-芳基化氨基酯。广泛的底物范围和良好的官能团耐受性是该策略的关键特征。
• Novel tetraalkyltetraboranes of the type B4R4, B4H2R4 and B4H4R4
  作者：Andreas Neu、Theo Mennekes、Peter Paetzold、Ulli Englert、Matthias Hofmann、Paul von Ragué Schleyer

  DOI：10.1016/s0020-1693(99)00058-4

  日期：1999.6

  The reduction of RBHal(2) (Hal = F, Cl, Br) with Na/K alloy gives the tetraboranes B4R4, B4H2R4 or their mixtures, depending on temperature, reaction time and solvent. We describe here (B4Bu4)-Bu-t, B-4((CH2Bu)-Bu-t)(4) (B4H2Bu4)-Bu-t, B4H2((CH2Bu)-Bu-t)(4) and B4H2(CMe2Et)(4). (B4Bu2)-Bu-t((CH2Bu)-Bu-t)(2) is formed by reducing the diborane Cl-B(Bu-t)-B((CH2Bu)-Bu-t)-Cl with Li. The conversion of (B4H2Bu4)-Bu-t into (B4H4Bu4)-Bu-t proceeds in three steps: (i) reduction (-->[(B4H2Bu4)-Bu-t](2-)); (ii)first protonation (-->[(B4H3Bu4)-Bu-t](-)), and (iii) second protonation (-->(B4H4Bu4)-Bu-t). The hypercloso-species B4R4 have: tetrahedral structures. The two opposite edges of a B-4 tetrahedron of the closo-B4H2R4 are bridged by H atoms (D-2d). The nido-species have a bicyclobutane-type B-4 skeleton; three of the four outside edges are bridged by H atoms; two terminal ligands are bound to one of the B atoms: H in exo- and Bu-t in endo-position (C-1). Structural evidence is based on low-temperature NMR spectra, ab initio geometries, and IGLO(DZ) calculations of the B-11 NMR shifts. Dynamical behavior of bridging H atoms is indicated by the NMR spectra at higher temperature. (C) 1999 Elsevier Science S.A. Pill rights reserved.
• Visible Light‐Mediated Late‐Stage Thioetherification of Mercaptopurine Derivatives
  作者：Yuhua Ge、Yijiang Peng、Ruoqian Xie、Yang Luo、Yangyan Li、Gang Chen

  DOI：10.1002/chem.202401774

  日期：2024.8.27

  We present herein a novel photo‐mediated homolytic C‐S bond formation for the preparation of alkylthiopurines and alkylthiopurine nucleosides. Despite the presence of reactive sites for the Minisci reaction, chemoselective S‐alkylation remained the predominant pathway. This method allows for the late‐stage introduction of a broad spectrum of alkyl groups onto the sulfur atom of unprotective mercaptopurine derivatives, encompassing 2‐, 6‐, and 8‐mercaptopurine rings. Organoborons serve as efficient and eco‐friendly alkylating reagents, providing advantages in terms of readily availability, stability, and reduced toxicity. Further derivatization of the thioetherified nucleosides, together with anti‐tumor assays, led to the discovery of potent anti‐tumor agents with an IC50 value reaching 6.1 µM (Comp. 31 for Jurkat).