2,2,6,6-tetramethyl-1-(undecyloxy)piperidine | 823179-57-3

• 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: 2,2,6,6-tetramethyl-1-(undecyloxy)piperidine
• 英文别名: 2,2,6,6-Tetramethyl-1-(undecyloxy)piperidine；2,2,6,6-tetramethyl-1-undecoxypiperidine
• CAS: 823179-57-3
• 化学式: C₂₀H₄₁NO
• 分子量: 311.552
• InChiKey: OCIGTYDBVVKREQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,6,6-tetramethyl-1-(undecyloxy)piperidine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到十一醛
  参考文献：
  名称：

  Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes

  摘要：

  Sodium 2,2,6,6-tetramethylpiperidine-N-oxide (TEMPO-Na+), generated by reduction of TEMPO. with sodium naphthalenide in THF, reacted with alkyl halides or acyl halides to produce O-alkylated or acylated TEMPOs, which were in turn oxidized with mCPBA or reduced with DIBAL-H to afford the corresponding aldehydes, thus accomplishing a new protocol for the halides-carbonyls conversion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.067
• 作为产物：
  描述：

  月桂酸 在 4-二甲氨基吡啶 、 copper acetylacetonate 、 四甲基乙二胺 、 双氧水 、 Diphenylphosphine oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 2,2,6,6-tetramethyl-1-(undecyloxy)piperidine
  参考文献：
  名称：

  铜催化烷基和磷自由基交叉偶联形成 C(sp3)-P 键

  摘要：

  介绍了一种 Cu I催化的以烷基和磷为中心的自由基的交叉偶联，以形成 C(sp 3 )-P 键。由脂肪酸和 H 2 O 2原位生成的二酰基过氧化物可作为烷基自由基的来源，也是从 H-P(O) 化合物生成磷自由基的引发剂。

  DOI：

  10.1021/acs.orglett.2c02454

文献信息

• Iron-Catalyzed Alkylazidation of 1,1-Disubstituted Alkenes with Diacylperoxides and TMSN₃
  作者：Rongbiao Wei、Haigen Xiong、Changqing Ye、Yajun Li、Hongli Bao

  DOI：10.1021/acs.orglett.0c00969

  日期：2020.4.17

  An iron-catalyzed radical alkylazidation of electron-deficient alkenes is reported. Alkyl diacyl peroxides work as the alkyl source, and trimethylsilyl azide acts as the azido reservoir. This method features mild reaction conditions, wide substrate scope, and good functional group tolerance, providing a range of α-azido esters, an α-azido ketone, and an α-azido cyanide in high yields. These azides

  报道了缺电子烯烃的铁催化的自由基烷基叠氮化。烷基二酰基过氧化物充当烷基源，三甲基甲硅烷基叠氮化物充当叠氮基储库。该方法的特点是反应条件温和，底物范围宽，官能团耐受性好，可以高产率提供各种α-叠氮基酯，α-叠氮基酮和α-叠氮基氰化物。这些叠氮化物可以容易地转移成多种氨基酸衍生物。
• Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides
  作者：Hui Chen、Shuhao Sun、Xuebin Liao

  DOI：10.1021/acs.orglett.9b01048

  日期：2019.5.17

  Decarboxylative cross-coupling of aliphatic acid anhydrides with vinyl triflates or halides was accomplished via nickel catalysis. This methodology works well with a broad array of substrates and features abundant functional group tolerance. Notably, our approach addresses the issue of safe and environmental installation of methyl or ethyl group into molecular scaffolds. The method possesses high chemoselectivity

  脂肪族酸酐与乙烯基三氟甲磺酸酯或卤化物的脱羧交叉偶联是通过镍催化实现的。这种方法学适用于各种各样的底物，并且具有丰富的官能团耐受性。值得注意的是，我们的方法解决了将甲基或乙基安全环保地安装到分子支架中的问题。当涉及脂族/芳族混合酸酐时，该方法具有对烷基的高化学选择性。此外，我们的策略可以改变各种酮。
• Unnatural α-Amino Acid Synthesized through α-Alkylation of Glycine Derivatives by Diacyl Peroxides
  作者：Hao Tian、Wentao Xu、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.0c01574

  日期：2020.7.2

  We have developed a protocol for catalyst- and additive-free α-alkylation reactions of glycine derivatives with diacyl peroxides, which proceed by a pathway involving addition of alkyl radicals to imine intermediates. The diacyl peroxide substrate acts as both alkylation agent and oxidizing agent, which means it is atom-economical. It was applied to various glycine derivatives, dipeptides, and a 3

  我们已经开发出用于甘氨酸衍生物与二酰基过氧化物的无催化剂和无添加剂的α-烷基化反应的方案，该方案通过涉及将烷基自由基加成至亚胺中间体的途径进行。过氧化二酰基的底物既充当烷基化剂又充当氧化剂，这意味着它是原子经济的。它已应用于各种甘氨酸衍生物，二肽和3,4-二氢喹喔啉-2（1 H）-one衍生物，并且可以克量进行，表明其可用于后期功能化。
• Iron‐Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides
  作者：Xiaotao Zhu、Changqing Ye、Yajun Li、Hongli Bao

  DOI：10.1002/chem.201701830

  日期：2017.8

  An iron‐catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C−C triple bonds and diverse α‐alkylated ketones were synthesized

  已经研究了以烷基过氧化物作为烷基化试剂的炔烃的铁催化的烷氧基化反应。烷基过氧化物可容易地从脂族酸获得，并且同时用作烷基化试剂和内部氧化剂。脂肪酸的伯，仲和叔烷基易于掺入C-C三键中，并合成了多种α-烷基化的酮。机理研究表明，该反应涉及高反应性烷基自由基。观察到铁（III）催化剂催化的月桂酸和水之间的独特平衡。
• Iron‐Catalyzed Decarboxylative Alkyl Etherification of Vinylarenes with Aliphatic Acids as the Alkyl Source
  作者：Wujun Jian、Liang Ge、Yihang Jiao、Bo Qian、Hongli Bao

  DOI：10.1002/anie.201612365

  日期：2017.3.20

  alkylating reagents, alkyl etherification of olefins with general alkyl groups has not been previously reported. In this work, a variety of alkyl diacyl peroxides and peresters generated from aliphatic acids have been found to enable the first iron‐catalyzed alkyl etherification of olefins with general alkyl groups. Primary, secondary and tertiary aliphatic acids are suitable for this reaction, delivering products

  由于缺乏有效的烷基化试剂，以前没有关于具有一般烷基的烯烃的烷基醚化的报道。在这项工作中，发现了由脂肪酸生成的各种烷基二酰基过氧化物和过酸酯，可以使具有一般烷基的烯烃首次进行铁催化的烷基醚化。伯，仲和叔脂族酸适用于该反应，可提供产率高达97％的产物。伯醇和仲醇反应良好，提供的产品收率高达91％。