1-N-benzyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine | 26460-91-3

• 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: 1-N-benzyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine
• 英文别名: 1-(benzyloxy)-2,2,6,6-tetramethylpiperidin-4-ol；benzyl-4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl；1-benzyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine；2,2,6,6-tetramethyl-1-phenylmethoxypiperidin-4-ol
• CAS: 26460-91-3
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: YKTNSHZLHPCCEO-UHFFFAOYSA-N

物化性质

• 沸点：
  354.8±52.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙酸 、 阻聚剂701 在 dipotassium peroxodisulfate 、 potassium carbonate 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以74%的产率得到1-N-benzyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine
  参考文献：
  名称：

  使用双相溶剂体系进行的羧酸的无金属脱羧氨基氧化

  摘要：

  据报道，使用TEMPO和其他衍生物作为自由基清除剂可使羧酸平滑氧化自由基脱羧。成功的关键是使用两相溶剂体系，以避免其他主要的副反应，例如过硫酸盐对TEMPO的氧化，并能够选择性地形成合成上有用的烷氧基胺。该方法不需要过渡金属，已成功用于抗抑郁药茚达林的新合成方法中。

  DOI：

  10.1039/d0ob01773f

文献信息

• TEMPO-Mediated Oxidative Deformylation of Aldehydes: Applications in the Synthesis of Polyketide Fragments
  作者：Andreas Kipke、Kai-Uwe Schöning、Mekhman Yusubov、Andreas Kirschning

  DOI：10.1002/ejoc.201701349

  日期：2017.12.15

  The TEMPO-mediated oxidative deformylation of aldehydes is reported that yields the TEMPO adducts which can be further oxidized to the corresponding ketones. The focus of this work was on the optimization of a synthetic protocol for use in natural product synthesis, specifically for the preparation of chiral backbones with 1,2-oxo functionalization found in polyketide antibiotics. In addition, the

  据报道，TEMPO 介导的醛氧化去甲酰化产生的 TEMPO 加合物可以进一步氧化成相应的酮。这项工作的重点是优化用于天然产物合成的合成方案，特别是用于制备在聚酮抗生素中发现的具有 1,2-氧代官能化的手性骨架。此外，在一锅法中将氧化去甲酰化与醇氧化成前体醛相结合。
• The Thermal Reaction of Sterically Hindered Nitroxyl Radicals with Allylic and Benzylic Substrates:  Experimental and Computational Evidence for Divergent Mechanisms
  作者：Joseph E. Babiarz、Glen T. Cunkle、Anthony D. DeBellis、David Eveland、Stephen D. Pastor、Sai P. Shum

  DOI：10.1021/jo020426r

  日期：2002.9.1

  reaction of stable sterically hindered nitroxyl radicals with benzylic and allylic substrates was investigated. An allyloxyamine derivative was obtained by the reaction of 2 molar equiv of a nitroxyl radical with an unactivated alkene. Experimental and computational evidence is consistent with a low-energy pathway involving addition of the nitroxyl radical to the double bond followed by H-atom abstraction

  研究了稳定的位阻硝基氧基与苄基和烯丙基底物的反应。通过2摩尔当量的硝酰基自由基与未活化的烯烃反应获得烯丙氧基胺衍生物。实验和计算证据与低能量途径一致，该途径涉及将硝酰自由基加成到双键上，然后通过另一等价的硝酰自由基从中间体中提取H原子。
• Process for the synthesis of 4-substituted N-[(alk-2-en-1-yl)oxy]-and N-aralkyloxy-2,2,6,6-tetraalkylpiperidines
  申请人：Ciba Specialty Chemicals Corporation

  公开号：US06211378B1

  公开（公告）日：2001-04-03

  An environmentally friendly process for the preparation of the 4-functionalized N—OR derivatives of 2,2,6,6-tetraalkylpiperidines involves the hydrogen peroxide of the corresponding N—H compound to form the corresponding N-oxyl derivative, reacting two equivalents of the N-oxyl compound with one equivalent of a compound having an allylic hydrogen, a benzylic hydrogen or an activated methine hydrogen to form one equivalent of the corresponding N—OH compound and one equivalent of the corresponding N—OR compound, and recycling the N—OH compound back to the corresponding N-oxyl compound using hydrogen peroxide or air.

  一种环保的方法用于制备2,2,6,6-四烷基哌啶的4-取代N—OR衍生物，该方法涉及使用过氧化氢将相应的N—H化合物转化为相应的N-氧化物衍生物，然后将两当量的N-氧化物化合物与一个具有烯丙基氢，苄基氢或活化甲烷氢的化合物的一个当量反应，形成一个相应的N—OH化合物和一个相应的N—OR化合物，最后使用过氧化氢或空气将N—OH化合物回收至相应的N-氧化物化合物。
• Process for the preparation of sterically hindered nitroxyl ethers
  申请人：Schöning Kai-Uwe

  公开号：US20100249401A1

  公开（公告）日：2010-09-30

  The present invention relates to a novel process for the preparation of a sterically hindered nitroxyl ether from the corresponding sterically hindered nitroxyl radical by reacting it with a carbonyl compound and a hydroperoxide. The compounds prepared by this process are effective stabilizers for polymers against harmful effects of light, oxygen and/or heat, as flame-retardants for polymers and as polymerization regulators.

  本发明涉及一种从相应的立体位阻的亚硝基自由基通过与羰基化合物和过氧化氢反应制备立体位阻的亚硝基醚的新工艺。通过该工艺制备的化合物是聚合物的有效稳定剂，可抵抗光、氧和/或热的有害影响，作为聚合物的阻燃剂和聚合物化合物的调节剂。
• Non-migrating 1-hydrocarbyloxy hindered amine compounds as polymer stabilizers
  申请人：CIBA-GEIGY AG

  公开号：EP0389419A1

  公开（公告）日：1990-09-26

  1-Hydrocarbyloxy substituted hindered amine compounds which also contain a reactive functional group such as hydroxy, amino, oxirane or carboxyl can be chemically attached to selected polymer substrates by condensation reactions to give polymers containing a chemically-bonded, non-migrating stabilizer having excellent stabilization efficacy for protecting said polymer substrate from the adverse effects of actinic light.

  1-Hydrocarbyloxy 取代的受阻胺化合物还含有羟基、氨基、环氧乙烷或羧基等活性官能团，可通过缩合反应与选定的聚合物基材发生化学键合，从而得到含有化学键合的非迁移稳定剂的聚合物，该稳定剂具有优异的稳定效果，可保护所述聚合物基材免受光辐射的不利影响。