3-(pyridin-4-yl)cyclopentan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(pyridin-4-yl)cyclopentan-1-one
• 英文别名: 3-(4-Pyridyl)cyclopentan-1-one；3-pyridin-4-ylcyclopentan-1-one
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: CBZLONNYXCLLFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氰基吡啶 、 2-环戊烯酮 在 bis(acetylacetonate)nickel(II) 、 四丁基高氯酸铵 、 sodium carbonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 3.0h， 以60%的产率得到3-(pyridin-4-yl)cyclopentan-1-one
  参考文献：
  名称：

  Electroreductive 4-Pyridylation of Electron-deficient Alkenes with Assistance of Ni(acac)₂

  摘要：

  An electroreductive 4-pyridylation of activated alkenes was developed in an undivided cell with the assistance of Ni(acac)(2) (acac = acetylacetone). This novel protocol is compatible with a broad range of electron-poor alkenes, which are commonly regarded as challenging substrates in the previous conventional approaches. Moreover, a series of cyclic voltammetric experiments were conducted to reveal the unique role of Ni(acac)(2) differentiating reduction process of reaction partners.

  DOI：

  10.1021/acs.orglett.0c01014

文献信息

• Metal-Free Synthesis of C-4 Substituted Pyridine Derivatives Using Pyridine-boryl Radicals via a Radical Addition/Coupling Mechanism: A Combined Computational and Experimental Study
  作者：Guoqiang Wang、Jia Cao、Liuzhou Gao、Wenxin Chen、Wenhao Huang、Xu Cheng、Shuhua Li

  DOI：10.1021/jacs.7b00823

  日期：2017.3.15

  that the pyridine-boryl radical generated in situ using 4-cyanopyridine and bis(pinacolato)diboron could be used as a bifunctional "reagent", which serves as not only a pyridine precursor but also a boryl radical. With the unique reactivity of such radicals, 4-substituted pyridine derivatives could be synthesized using α,β-unsaturated ketones and 4-cyanopyridine via a novel radical addition/C-C coupling

  密度泛函理论研究表明，使用 4-氰基吡啶和双（频哪醇）二硼原位生成的吡啶-硼基自由基可用作双功能“试剂”，其不仅可用作吡啶前体，还可用作硼基自由基。由于这些自由基的独特反应性，可以使用α,β-不饱和酮和4-氰基吡啶通过新型自由基加成/CC偶联机制合成4-取代吡啶衍生物。进行了几个对照实验，为所提出的机制提供支持性证据。除了烯酮，范围还可以扩展到广泛的硼基自由基受体，包括各种醛和酮、芳基亚胺和炔酮。最后，这种转化应用于复杂药物分子的后期修饰。
• Electroreductive 4-Pyridylation of Electron-deficient Alkenes with Assistance of Ni(acac)₂
  作者：Sheng Zhang、Lijun Li、Xinru Li、Junqi Zhang、Kun Xu、Guigen Li、Michael Findlater

  DOI：10.1021/acs.orglett.0c01014

  日期：2020.5.1

  An electroreductive 4-pyridylation of activated alkenes was developed in an undivided cell with the assistance of Ni(acac)(2) (acac = acetylacetone). This novel protocol is compatible with a broad range of electron-poor alkenes, which are commonly regarded as challenging substrates in the previous conventional approaches. Moreover, a series of cyclic voltammetric experiments were conducted to reveal the unique role of Ni(acac)(2) differentiating reduction process of reaction partners.