2,2,6,6-tetramethyl-1-(1-phenylpropan-2-yloxy)piperidine | 197246-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,6,6-tetramethyl-1-(1-phenylpropan-2-yloxy)piperidine
• CAS: 197246-26-7
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: YETCXYWHJBHYDA-UHFFFAOYSA-N

物化性质

• 沸点：
  346.3±35.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  丙烯腈 、 diphenyliodonium triflate 、 2,2,6,6-四甲基哌啶氧化物 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 [Cu(dpp)₂]PF₆ 、 2-methyl-N-(pyridin-2-ylmethylene)propan-2-amine 作用下， 以 氘代乙腈 为溶剂， 生成 2,2,6,6-tetramethyl-1-(1-phenylpropan-2-yloxy)piperidine
  参考文献：
  名称：

  A Modular Dual‐Catalytic Aryl‐Chlorination of Alkenes

  摘要：

  Alkyl chlorides are a class of versatile building blocks widely used to generate C(sp3)‐rich scaffolds through transformation such as nucleophilic substitution, radical addition reactions and metal‐catalyzed cross‐coupling processes. Despite their utility in the synthesis of high‐value functional molecules, distinct methods for the preparation of alkyl chlorides are underrepresented. Here, we report a visible‐light‐mediated dual catalysis strategy for the modular synthesis of highly functionalized and structurally diverse arylated chloroalkanes via the coupling of diaryliodonium salts, alkenes and potassium chloride. A distinctive aspect of this transformation is a ligand‐design‐driven approach for the development of a copper(II)‐based atom‐transfer catalyst that enables the aryl‐chlorination of electron‐poor alkenes, complementing its iron(III)‐based counterpart that accommodates non‐activated aliphatic alkenes and styrene derivatives. The complementarity of the two dual catalytic systems allows the efficient aryl‐chlorination of alkenes bearing different stereo‐electronic properties and a broad range of functional groups, maximizing the structural diversity of the 1‐aryl, 2‐chloroalkane products.

  DOI：

  10.1002/anie.202405939

文献信息

• A new mild radical route to 3-substituted maleimides using organoboroles
  作者：Peter Birch、Andrew F. Parsons、Paul Cross

  DOI：10.1016/j.tetlet.2011.12.012

  日期：2012.2

  A new, mild, radical route for the synthesis of 3-substituted maleimides has been developed. This new method incorporates alkene hydroboration, conjugate addition-aminoxylation and TEMPO-H elimination in a one-pot procedure, using cheap, readily available starting materials. A variety of 3-substituted maleimides have been prepared in good to excellent yield.

  已经开发出一种新的，温和的，自由基的路线来合成3-取代的马来酰亚胺。这种新方法使用便宜的，易于获得的起始原料，通过一锅法将烯烃氢硼化，共轭加成-氨氧基化和TEMPO-H消除反应结合在一起。已经以良好至优异的产率制备了各种3-取代的马来酰亚胺。
• Engaging Alkenes in Metallaphotoredox: A Triple Catalytic, Radical Sorting Approach to Olefin-Alcohol Cross-Coupling
  作者：Qinyan Cai、Iona M. McWhinnie、Nathan W. Dow、Amy Y. Chan、David W. C. MacMillan

  DOI：10.1021/jacs.4c02316

  日期：2024.5.8

  reactivity via metal-hydride hydrogen atom transfer (MHAT), although metallaphotoredox methodologies invoking this strategy remain underdeveloped. Importantly, merging MHAT activation with metallaphotoredox could enable the cross-coupling of olefins with feedstock partners such as alcohols, which undergo facile open-shell activation via photocatalysis. Herein, we report the first C(sp3)–C(sp3) coupling

  Metallaphotoredox 交叉偶联是一种成熟的策略，用于通过单电子反应性生成临床上享有特权的脂肪族支架。相应地，扩展金属光氧化还原以包含新的 C（sp3） 偶联伴侣可以为一种新的、医学相关的化学空间提供入口。特别是，烯烃丰富、稳定，并且能够通过金属氢化物氢原子转移 （MHAT） 实现多功能的 C（sp3） 自由基反应性，尽管调用这种策略的金属光氧化还原方法仍然不成熟。重要的是，将 MHAT 活化与金属光氧化还原合并可以使烯烃与醇等原料伙伴发生交叉偶联，这些原料伙伴通过光催化进行简单的开壳活化。在此，我们报道了 MHAT 活化烯烃与醇的首次 C（sp3）–C（sp3） 偶联，通过三重共催化进行脱氧氢烷基化。通过协同 Ir 光氧化还原、Mn MHAT 和 Ni 自由基分选途径，这种分支选择性方案将不同的烯烃与具有显著官能团耐受性的甲醇或伯醇配对，以实现复杂脂肪族框架的快速构建。