哌啶,2,2,6,6-四甲基-1-[(3-甲基-2-丁烯基)氧代]- | 131749-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 哌啶,2,2,6,6-四甲基-1-[(3-甲基-2-丁烯基)氧代]-
• 英文名称: 2,2,6,6-tetramethyl-N-(3-methylbut-2-enyloxy)piperidine
• 英文别名: 2,2,6,6-tetramethyl-1-((3-methylbut-2-en-1-yl)oxy)piperidine；2,2,6,6-Tetramethyl-1-[(3-methylbut-2-en-1-yl)oxy]piperidine；2,2,6,6-tetramethyl-1-(3-methylbut-2-enoxy)piperidine
• CAS: 131749-90-1
• 化学式: C₁₄H₂₇NO
• 分子量: 225.374
• InChiKey: ZNHOQVYHSNDZAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 1-氯-3-甲基-2-丁烯 在 萘 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到哌啶,2,2,6,6-四甲基-1-[(3-甲基-2-丁烯基)氧代]-
  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

文献信息

• Tandem Anionic oxy‐Cope Rearrangement/Oxygenation Reactions as a Versatile Method for Approaching Diverse Scaffolds
  作者：Michal Šimek、Kateřina Bártová、Radek Pohl、Ivana Císařová、Ullrich Jahn

  DOI：10.1002/anie.201916188

  日期：2020.4.6

  Tandem anionic oxy‐Cope rearrangement/radical oxygenation reactions provide δ,ϵ‐unsaturated α‐(aminoxy) carbonyl compounds, which serve as convenient precursors to diverse compound classes. Functionalized carbocycles are accessible by very rare all‐carbon 5‐endo‐trig cyclizations, but also common 5‐exo‐trig radical cyclizations, based on the persistent radical effect. The tandem reactions can be further

  串联阴离子氧对付重排/自由基氧合反应可提供δ，β-不饱和α-（氨氧基）羰基化合物，可作为各种化合物类别的便捷前体。功能化的碳环是通过访问非常罕见的全碳5周内-trig的环化反应，但也常见5-外-trig自由基环化的基础上，持久根治的效果。可以通过高度非对映选择性烯丙基化或还原步骤进一步扩展串联反应，从而得到复杂的骨架。
• Howell, Amy R.; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1990, # 10, p. 2715 - 2720
  作者：Howell, Amy R.、Pattenden, Gerald

  DOI：——

  日期：——
• Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes
  作者：Tsutomu Inokuchi、Hiroyuki Kawafuchi

  DOI：10.1016/j.tet.2004.09.067

  日期：2004.12

  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.