tert-butyl 4-(pyrazin-2-yl)piperidine-1-carboxylate | 921613-02-7

• 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-(pyrazin-2-yl)piperidine-1-carboxylate
• 英文别名: 4-(2-Pyrazinyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester；tert-butyl 4-pyrazin-2-ylpiperidine-1-carboxylate
• CAS: 921613-02-7
• 化学式: C₁₄H₂₁N₃O₂
• 分子量: 263.34
• InChiKey: QAOOBSLGNQLFIP-UHFFFAOYSA-N

物化性质

• 沸点：
  379.9±42.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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-(pyrazin-2-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 2-(piperidin-4-yl)pyrazine
  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：

  2-碘吡嗪 、 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-(pyrazin-2-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

• 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。
• Potent heteroarylpiperidine and carboxyphenylpiperidine 1-alkyl-cyclopentane carboxamide CCR2 antagonists
  作者：Alexander Pasternak、Stephen D. Goble、Pasquale P. Vicario、Jerry Di Salvo、Julia M. Ayala、Mary Struthers、Julie A. DeMartino、Sander G. Mills、Lihu Yang

  DOI：10.1016/j.bmcl.2007.12.029

  日期：2008.2

  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.