tert-butyl 4-(pyrimidin-5-yl)piperidine-1-carboxylate | 1019206-22-4

• 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: tert-butyl 4-(pyrimidin-5-yl)piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-pyrimidin-5-ylpiperidine-1-carboxylate；tert-butyl 4-pyrimidin-5-ylpiperidine-1-carboxylate
• CAS: 1019206-22-4
• 化学式: C₁₄H₂₁N₃O₂
• 分子量: 263.34
• InChiKey: AAMZRIODGCRXBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  383.5±35.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(pyrimidin-5-yl)piperidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 5-(Piperidin-4-yl)pyrimidine
  参考文献：
  名称：

  Potent heteroarylpiperidine and carboxyphenylpiperidine 1-alkyl-cyclopentane carboxamide CCR2 antagonists

  摘要：

  This report describes replacement of the 4-(4-fluorophenyl)piperidine moiety in our CCR2 antagonists with 4-heteroaryl piperidine and 4-(carboxyphenyl)-piperidine subunits. Some of the resulting analogs retained potency in our CCR2 binding assay and had improved selectivity versus the I-Kr channel; poor selectivity against I-Kr had been a liability of earlier analogs in this series. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.029
• 作为产物：
  描述：

  5-碘嘧啶 、 N-Boc-4-碘哌啶 在 tris(dibenzylideneacetone)dipalladium (0) 1,2-二溴乙烷 、 锌 、 三甲基氯硅烷 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 4-(pyrimidin-5-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  Potent heteroarylpiperidine and carboxyphenylpiperidine 1-alkyl-cyclopentane carboxamide CCR2 antagonists

  摘要：

  This report describes replacement of the 4-(4-fluorophenyl)piperidine moiety in our CCR2 antagonists with 4-heteroaryl piperidine and 4-(carboxyphenyl)-piperidine subunits. Some of the resulting analogs retained potency in our CCR2 binding assay and had improved selectivity versus the I-Kr channel; poor selectivity against I-Kr had been a liability of earlier analogs in this series. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.029

文献信息

• Visible-Light Enabled C(s<i>p</i>³)–C(s<i>p</i>²) Cross-Electrophile Coupling via Synergistic Halogen-Atom Transfer (XAT) and Nickel Catalysis
  作者：Girish Suresh Yedase、Avishek Kumar Jha、Veera Reddy Yatham

  DOI：10.1021/acs.joc.2c00251

  日期：2022.4.15

  We herein report the first visible-light-mediated cross-coupling of unactivated alkyl iodides with aryl bromides through synergistic halogen atom transfer (XAT) and nickel catalysis. This simple protocol operates under mild reaction conditions and tolerates a variety of functional groups affording C(sp3)–C(sp2) cross-coupling products in good to moderate yields.

  我们在此报告了第一个可见光介导的未活化烷基碘与芳基溴通过协同卤素原子转移 (XAT) 和镍催化的交叉偶联。这个简单的协议在温和的反应条件下运行，并容忍各种官能团，以良好至中等的产率提供 C(s p 3 )–C(s p 2 ) 交叉偶联产物。
• ART─An Amino Radical Transfer Strategy for C(sp²)–C(sp³) Coupling Reactions, Enabled by Dual Photo/Nickel Catalysis
  作者：Elisabeth Speckmeier、Thomas C. Maier

  DOI：10.1021/jacs.2c03220

  日期：2022.6.8

  Introducing the novel concept of amino radical transfer (ART) enables the use of easily accessible and commercially available alkyl boronic esters as cross-coupling partners for aryl halides in dual photoredox/nickel catalysis mediated by visible light. Activation of otherwise photochemically innocent boronic esters by radicals generated from primary or secondary alkylamines gives rise to an outstanding

  引入氨基自由基转移 (ART) 的新概念使得在可见光介导的双光氧化还原/镍催化中使用易于获得和市售的烷基硼酸酯作为芳基卤化物的交叉偶联伙伴成为可能。由伯或仲烷基胺产生的自由基激活其他光化学无害的硼酸酯，在温和、快速和空气稳定的反应中产生出色的官能团耐受性。如 50 多个示例所示，包括未受保护的醇、胺和羧酸，该反应允许快速访问有机合成和药物化学的相关支架。与 C(sp 2 )–C(sp 3的现有方法相比) 偶联可以通过 ART 概念实现非凡的普遍性，采用一组优化的反应条件。由于其选择性，该转化也可用于后期功能化，如药物分子的三个示例性合成所示。此外，证明了该反应成功的一对一可扩展性高达克级，而无需任何进一步的预防措施或流动系统。
• (Phenoxyimine)nickel-Catalyzed C(sp²)–C(sp³) Suzuki–Miyaura Cross-Coupling: Evidence for a Recovering Radical Chain Mechanism
  作者：L. Reginald Mills、Eric M. Simmons、Heejun Lee、Eva Nester、Junho Kim、Steven R. Wisniewski、Matthew V. Pecoraro、Paul J. Chirik

  DOI：10.1021/jacs.4c01474

  日期：2024.4.10

  the C(sp2)–C(sp3) Suzuki–Miyaura cross coupling of (hetero)arylboronic acids with alkyl bromides. With 5 mol % of the optimal (MeOMeFI)Ni(Aryl)(DMAP) precatalyst, the scope of the cross-coupling reaction was established and included a variety of (hetero)arylboronic acids and alkyl bromides (>50 examples, 33–97% yield). A β-hydride elimination–reductive elimination sequence from reaction with potassium

  合成了苯氧亚胺 (FI)–镍(II)(2-甲苯基)(DMAP) 化合物，并作为（杂）芳基硼酸与烷基的 C(sp 2 )–C(sp 3 ) Suzuki-Miyaura 交叉偶联的预催化剂进行了评估溴化物。使用 5 mol% 的最佳 (Me OMe FI)Ni(芳基)(DMAP) 预催化剂，建立了交叉偶联反应的范围，包括各种（杂）芳基硼酸和烷基溴（> 50 个示例，33 –97% 的产率）。与异丙醇钾碱反应产生 (FI) 镍 (0) 酸钾的 β-氢化物消除-还原消除序列被确定为负责从烷基溴中提取卤素原子的催化剂活化途径。 NMR 和 EPR 光谱相结合，确定 (FI) 镍 (II)-芳基配合物在催化过程中处于静止状态，没有证据表明存在长寿命有机自由基或奇电子镍中间体。这些数据表明，自由基链是短暂的，很容易终止，并且还支持“恢复自由基链”过程，通过该过程，(FI)镍(II)-芳基化合物不断地（
• Metal-Free Coupling of Saturated Heterocyclic Sulfonylhydrazones with Boronic Acids
  作者：Daniel M. Allwood、David C. Blakemore、Alan D. Brown、Steven V. Ley

  DOI：10.1021/jo402526z

  日期：2014.1.3

  The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp(2)-sp(3) linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.
• Ni/Photoredox-Catalyzed C(sp²)–C(sp³) Cross-Coupling of Alkyl Pinacolboronates and (Hetero)Aryl Bromides
  作者：Anthony N. Cauley、Antonio Ramirez、Chandan L. Barhate、Andrew F. Donnell、Purnima Khandelwal、Melda Sezen-Edmonds、Trevor C. Sherwood、Jack L. Sloane、Cullen L. Cavallaro、Eric M. Simmons

  DOI：10.1021/acs.orglett.2c01942

  日期：2022.8.12