三氟甲醇酸N,N,N-三甲基甲铵 | 189997-61-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 三氟甲醇酸N,N,N-三甲基甲铵
• 英文名称: tetramethylammonium trifluoromethoxide
• 英文别名: tetramethylammonium trifluoromethanolate；tetramethylammonium trifluoromethoxylate；Tetramethylammonium-trifluoromethanolate；tetramethylazanium;trifluoromethanolate
• CAS: 189997-61-3
• 化学式: CF₃O*C₄H₁₂N
• 分子量: 159.152
• InChiKey: RXOIVYZLFDYMDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tosyl-(2,2-dimethyl)-pent-4-enylamine 、 三氟甲醇酸N,N,N-三甲基甲铵 在 双(乙腈)氯化钯(II) 、 Selectfluor 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以11%的产率得到3,3-Dimethyl-1-(4-methylphenyl)sulfonyl-5-(trifluoromethoxy)piperidine
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes

  摘要：

  The first catalytic trifluoromethoxylation of unactivated alkenes has been developed, in which Pd(CH3CN)(2)Cl-2 was used as catalyst, AgOCF3 as trifluoromethoxide source, and Selectfluor-BF4 as oxidant. A variety of 3-OCF3 substituted piperidines were selectively obtained in good yields. Direct evidence was provided to address the facile reductive elimination of Pe(IV)-OCF3 complex to form sp(3) C-OCF3 bond.

  DOI：

  10.1021/jacs.5b10971
• 作为产物：
  描述：

  氟光气 、 四甲基氟化铵 以 二氯甲烷 为溶剂， 生成 三氟甲醇酸N,N,N-三甲基甲铵
  参考文献：
  名称：

  Versatile application of trifluoromethyl triflate

  摘要：

  Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of 'masked' difluorophosgene. Anhydrous F(-) sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.105

文献信息

• PRODUCTION OF COMPOUNDS COMPRISING CF30 GROUPS
  申请人：Ignatyev Nikolai (Mykola)

  公开号：US20110082312A1

  公开（公告）日：2011-04-07

  The present invention relates to a process for the preparation of compounds containing CF 3 O groups using compounds containing at least one group Y, in which Y=—Hal, —OSO 2 (CF 2 ) z F, —OSO 2 C z H 2z+1 (z=1-10), —OSO 2 F, —OSO 2 Cl, —OC(O)CF 3 — or —OSO 2 Ar, to a process for the preparation of compounds containing CF 3 O groups using KOCF 3 and/or RbOCF 3 , and to novel compounds containing CF 3 O groups, and to the use thereof.

  本发明涉及一种利用含有至少一个基团Y的化合物制备含有CF3O基团的化合物的方法，其中Y=—Hal，—OSO2(CF2)zF，—OSO2CzH2z+1(z=1-10)，—OSO2F，—OSO2Cl，—OC(O)CF3—或—OSO2Ar；涉及一种利用KOCF3和/或RbOCF3制备含有CF3O基团的化合物的方法，以及涉及含有CF3O基团的新化合物及其用途。
• Quaternary Ammonium Trifluoromethoxide Salts as Stable Sources of Nucleophilic OCF₃
  作者：Josiah J. Newton、Benson J. Jelier、Michael Meanwell、Rainer E. Martin、Robert Britton、Chadron M. Friesen

  DOI：10.1021/acs.orglett.0c00099

  日期：2020.3.6

  methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability

  亲核叔胺与三氟甲基和五氟乙基甲基醚的反应分别以高收率提供了三氟甲基季铵盐（NR4OCF3）和五氟乙氧基盐（NR4OCF2CF3）盐。本文公开的新的三氟甲醇盐在固态和在溶液中均在延长的时间内具有独特的稳定性，这是对现代试剂的补充。在这里，我们描述了一系列NR4OCF3盐的制备，它们的长期稳定性以及在取代反应中的效用。
• Silver-mediated direct trifluoromethoxylation of α-diazo esters via the ⁻OCF₃ anion
  作者：Gao-Feng Zha、Jia-Bin Han、Xiao-Qian Hu、Hua-Li Qin、Wan-Yin Fang、Cheng-Pan Zhang

  DOI：10.1039/c6cc03040h

  日期：——

  Silver-mediated direct trifluoromethoxylation of α-diazo esters and ketosteroid was disclosed.

  银介导的α-重氮酯和酮类固醇的直接三氟甲氧基化反应被揭示。
• Über die Reaktionen von (CH₃)₄N⁺I^-, (CH₃)₄ <sub />N⁺ICl₂ ^-, (CH₃)₄N⁺ICl₄ ^- und (CH₃)₄N⁺Cl^- mit Trifluormethylhypochlorit CF₃OCl / The Reactions of (CH₃)₄N⁺I^-, ( CH₃)₄N⁺ICl₂ ^-, (CH₃)₄N⁺ICl₄ ^- and (CH₃)₄N₊Cl^- with Trifluoromethylhypochlorite CF₃OCl
  作者：Rolf Minkwitz、Raimund Bröchler

  DOI：10.1515/znb-1997-0317

  日期：1997.3.1

  CF3OCl have been demonstrated by the reactions with different iodate salts like (CH3)4N+I-, (CH3)4N+ICl2- and (CH3)4N +ICl4- . At -70°C all reactions give hexafluoroiodate(V ) salts IF6- . In contrast, the reaction of CF3OCl with (CH3)4N+Cl+ yields (CH3)4N+OCF3-. The products have been characterized by vibrational and NMR spectra.

  摘要 CF3OCl 的氟化性质已通过与不同碘酸盐如 (CH3)4N+I-、(CH3)4N+ICl2- 和 (CH3)4N +ICl4- 的反应得到证实。在 -70°C 下，所有反应均生成六氟碘酸盐 (V ) IF6- 。相反，CF3OCl与(CH3)4N+Cl+的反应产生(CH3)4N+OCF3-。产物已通过振动和核磁共振光谱表征。
• Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers
  作者：Michał Jakubczyk、Satenik Mkrtchyan、Mohanad Shkoor、Suneel Lanka、Šimon Budzák、Miroslav Iliaš、Marek Skoršepa、Viktor O. Iaroshenko

  DOI：10.1021/jacs.2c02611

  日期：2022.6.15

  Increased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino group

  在有机合成和药物化学中对三氟甲氧基的兴趣日益增加，这引发了对适用于天然产物和高度功能化化合物的新的、选择性的、通用的和更快的方法的需求，这些方法适用于“命中率”活动的后期阶段。应用 pyrylium tetrafluoroborate，我们开发了一种机械化学方案，以选择性地用 OCF 3官能团取代芳族氨基。我们方法的范围包括 31 个环取代苯胺的例子，包括酰胺和磺胺。以优异的产率获得了预期的 S N Ar 产品。所提出的简洁方法为制药行业开辟了通往新化学空间的途径。