4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate | 136708-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate
• 英文别名: 4-acetamido-2,2,6,6-tetramethylpiperidine acetate；4-acetamido-2,2,6,6-tetramethylpiperidin-1-ium acetate；4-acetamido-2,2,6,6-tetramethylpiperidinium acetate；2,2,6,6-tetramethylpiperidin-4-acetamide acetate；N-(2,2,6,6-tetramethyl-[4]piperidyl)-acetamide; acetate；N-(2,2,6,6-Tetramethyl-[4]piperidyl)-acetamid; Acetat；4-Acetamido-2,2,6,6-tetramethylpiperidinium acetate；N-(2,2,6,6-tetramethylpiperidin-1-ium-4-yl)acetamide;acetate
• CAS: 136708-43-5
• 化学式: C₂H₄O₂*C₁₁H₂₂N₂O
• 分子量: 258.361
• InChiKey: MTGKTFHFXVGTLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate 在 氢氧化钾 、 potassium carbonate 、 三乙胺 作用下， 以 水 、 苯 为溶剂， 反应 102.25h， 生成 4-异硫氰酰基-2,2,6,6-四甲基哌啶-1-氧基自由基
  参考文献：
  名称：

  一氧化氮与含硫化合物II的反应[1]。鉴于硫光气还原硝基基团，制备带有异硫氰酸酯取代基的硝基氧化物

  摘要：

   考察了硫光气与2,2,6,6-四甲基哌啶-1-氧基（用作模型硝基氧基）的反应。鉴定出2,2,6,6-四甲基哌啶和2,2,6,6-四甲基-1-羟基哌啶为产物。该反应与硫光气与氨基的反应没有竞争性。因此，由硫光气和含有氨基取代基的氮氧化物合成了具有异硫氰酸酯基的三种氮氧化物。

  DOI：

  10.1007/s00706-002-0572-x
• 作为产物：
  描述：

  2,2,6,6-四甲基-4-哌啶酮肟 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate
  参考文献：
  名称：

  Electron Paramagnetic Resonance (EPR) Study of Spin-Labeled Camptothecin Derivatives: A Different Look of the Ternary Complex

  摘要：

  Camptothecin (CPT) derivatives are clinically effective poisons of DNA topoisomerase I (Top 1) able to form a ternary complex with the Top1 DNA complex. The aim of this investigation was to examine the dynamic aspects of the ternary complex formation by means of site-directed spin labeling electron paramagnetic resonance (SDSL-EPR). Two semisynthetic CPT derivatives bearing the paramagnetic moiety were synthesized, and their biological activity was tested. A 22-mer DNA oligonucleotide sequence with high affinity cleavage site for Top1 was also synthesized. EPR experiments were carried out on modified CPT in the presence of DNA, of Top1, or of both. In the last case, a slow motion component in the EPR signal appeared, indicating the formation of the ternary complex. Deconvolution of the EPR spectrum allowed to obtain the relative drug amounts in the complex. It was also possible to demonstrate that the residence time of CPT "trapped" in the ternary complex is longer than hundreds of microseconds.

  DOI：

  10.1021/jm101232t

文献信息

• Oxidation of α-Trifluoromethyl Alcohols Using a Recyclable Oxoammonium Salt
  作者：Christopher B. Kelly、Michael A. Mercadante、Trevor A. Hamlin、Madison H. Fletcher、Nicholas E. Leadbeater

  DOI：10.1021/jo301477s

  日期：2012.9.21

  method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2

  描述了使用氧铵盐4-乙酰氨基-2,2,6,6-四甲基哌啶-1-氧铵四氟硼酸（1）将α-三氟甲基醇氧化为三氟甲基酮（TFMK）的简单，温和的方法。在碱性条件下，氧化迅速进行，并提供良好的TFMKs收率，而不会同时形成水合物。氧化的副产物4-乙酰氨基-2,2,6,6-四甲基-1-哌啶基氧基（1c）易于回收，可以方便地再氧化以再生氧代铵盐。
• Oxidation of primary and secondary alcohols by 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in aqueous media
  作者：Matthew R. Luderer、Audrey N. Mamros、Phillip R. Sharrow、William E. Weller、Mark R. Luderer、Justin D. Fair、Kristina O. Pazehoski

  DOI：10.3998/ark.5550190.0012.504

  日期：——

  The water soluble oxidant 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 1 oxidizes primary and secondary aliphatic, primary allylic, and primary and secondary benzylic alcohols to their corresponding aldehydes and ketones in aqueous media in good to excellent yields.

  水溶性氧化剂 4-乙酰氨基-2,2,6,6-四甲基哌啶-1-氧代四氟硼酸铵 1 在水性介质中将伯和仲脂肪族、伯烯丙醇以及伯和仲苄醇氧化成相应的醛和酮优良的产量。
• Preparation of Some Homologous TEMPO Nitroxides and Oxoammonium Salts; Notes on the NMR Spectroscopy of Nitroxide Free Radicals; Observed Radical Nature of Oxoammonium Salt Solutions Containing Trace Amounts of Corresponding Nitroxides in an Equilibrium Relationship
  作者：James M. Bobbitt、Nicholas A. Eddy、Clyde X. Cady、Jing Jin、Jose A. Gascon、Svetlana Gelpí-Dominguez、Jerzy Zakrzewski、Martha D. Morton

  DOI：10.1021/acs.joc.7b00846

  日期：2017.9.15

  homologous nitroxide radicals have been prepared and characterized. The oxidation properties of the salts have been explored. The direct 13C NMR and EPR spectra of the nitroxide free radicals and the oxoammonium salts, along with TEMPO and its oxoammonium salt, have been successfully measured with little peak broadening of the NMR signals. In the spectra of all ten compounds (nitroxides and corresponding

  制备并表征了三种新的同源TEMPO氧铵盐和三个同源的氮氧自由基。已经探索了盐的氧化性质。直接13已成功测量了氮氧化物自由基和氧代铵盐以及TEMPO及其氧代铵盐的C NMR和EPR光谱，而NMR信号的峰展宽很小。在所有十种化合物（氮氧化物和相应的氧铵盐）的光谱中，2,2,6,6-四甲基哌啶核中的碳均未出现，表明其具有顺磁性。氧铵盐溶液中这种不可预测的整体顺磁性是由氧化还原平衡所解释的，如氧铵盐和痕量相应的一氧化氮之间所示。该平衡通过具有N-乙酰基取代基的氮氧化物与具有较长酰基侧链的氧铵盐之间的电子交换反应得以证实。
• A Revised Preparation of (4-Acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate: Reagents for Stoichiometric Oxidations of Alcohols
  作者：James Bobbitt、Leon J. Tilley、Stephanie Murray、Casey Camire、Nicholas Eddy

  DOI：10.1055/s-0032-1317861

  日期：——

  Abstract Revised preparations of (4-acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and the corresponding oxoammonium salt, 4-acetamido-2,2,6,6-tetramethyl-1-oxoammonium tetrafluoroborate are presented together with some of the important properties of these two oxidizing­ reagents. Revised preparations of (4-acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and the corresponding oxoammonium salt, 4-acetamido-2

  摘要 一起列出了（4-乙酰氨基-2,2,6,6-四甲基哌啶-1-基）氧基和相应的氧铵盐，4-乙酰氨基-2,2,6,6-四甲基-1-氧铵四氟硼酸的修订版制剂具有这两种氧化剂的一些重要特性。 一起列出了（4-乙酰氨基-2,2,6,6-四甲基哌啶-1-基）氧基和相应的氧铵盐，4-乙酰氨基-2,2,6,6-四甲基-1-氧铵四氟硼酸的修订版制剂具有这两种氧化剂的一些重要特性。
• Harries, Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 176
  作者：Harries

  DOI：——

  日期：——