potassium;2-oxo-4-pyridin-3-ylbut-3-enoate | 1000400-72-5

• 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: potassium;2-oxo-4-pyridin-3-ylbut-3-enoate
• CAS: 1000400-72-5
• 化学式: C₉H₆NO₃*K
• 分子量: 215.25
• InChiKey: DZFFVTFRAAKDNB-UHFFFAOYSA-M

物化性质

• 熔点：
  239 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -3.58
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.09
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  potassium;2-oxo-4-pyridin-3-ylbut-3-enoate 在 1,5-二氮杂双环[4.3.0]壬-5-烯 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 2-(trans-5-benzoyl-6-(pyridin-3-yl)-5,6-dihydroindolizin-7-yl)-2-oxoacetate
  参考文献：
  名称：

  碱促进 [4 + 2] 吡咯-2-甲醛衍生物与 β,γ-不饱和 α-酮酯的环化：5,6-二氢吲哚的合成

  摘要：

  开发了吡咯-2-甲醛衍生物与 β,γ-不饱和 α-酮酯的碱促进 [4 + 2] 环化反应，用于合成多取代的 5,6-二氢二氢吲哚。以DBN为碱，反应在温和的条件下顺利进行，以中等到高的收率提供目标产物，并且可以容忍许多有用的官能团。

  DOI：

  10.1039/d2ob01903e
• 作为产物：
  描述：

  3-吡啶甲醛 、 丙酮酸 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 potassium;2-oxo-4-pyridin-3-ylbut-3-enoate
  参考文献：
  名称：

  Synthesis and biological evaluation of α-ketoamides as inhibitors of the Dengue virus protease with antiviral activity in cell-culture

  摘要：

  The development of small molecule inhibitors of the viral protease is of considerable interest for the treatment of emergent flaviviral diseases such as Dengue or West Nile fever. Until today little progress has been made in finding drug-like compounds that inhibit the protease and provide a starting point for lead optimization. We describe here the initial steps of a drug discovery effort that focused on the styryl pharmacophore, combined with a ketoamide function to serve as electrophilic trap for the catalytic serine. This resulted in a fragment-like lead compound with reasonable target affinity and good ligand efficiency, which was extensively modified to explore structure-activity relationships. Selected compounds were cross-tested against the West Nile virus protease and thrombin, indicating that selectivity for one or more flaviviral proteases can be achieved. Finally, the antiviral activity of several protease inhibitors was confirmed in a cell-culture model of Dengue virus replication. The SAR presented here may serve as starting point for further drug discovery efforts with the aim of targeting flaviviral proteases. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.015

文献信息

• Facile Synthesis of 2,2-Diacyl Spirocyclohexanones via an N-Heterocyclic Carbene-Catalyzed Formal [3C + 3C] Annulation
  作者：Yaru Gao、Dehai Liu、Zhenqian Fu、Wei Huang

  DOI：10.1021/acs.orglett.8b03892

  日期：2019.2.15

  A novel strategy for the construction of 2,2-diacyl spirocyclohexanones 3 has been demonstrated on the basis of an NHC-catalyzed [3C + 3C] annulation of potassium 2-oxo-3-enoates with 2-ethylidene 1,3-indandiones. Furthermore, enantioenriched 3 was obtained in good to excellent yields with good enantioselectivities when chiral N-heterocyclic carbene (NHC) was employed. Notably, ring opening of the

  为2,2-二酰基spirocyclohexanones建设的新策略3已经证明钾2-氧-3- enoates与2-亚乙基-1,3- indandiones一个NHC催化[3C + 3C]环的基础上。此外，当使用手性N-杂环卡宾（NHC）时，以良好的对映选择性良好地获得优异的对映体富集的3。值得注意的是，所得的2，2-二酰基螺环己酮3与肼的开环导致邻苯二氮酮的形成具有良好至优异的产率。