5-methyl-3-(pyridin-2-yl)oxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-methyl-3-(pyridin-2-yl)oxazolidin-2-one
• 英文别名: 5-Methyl-3-pyridin-2-yl-1,3-oxazolidin-2-one；5-methyl-3-pyridin-2-yl-1,3-oxazolidin-2-one
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: QBHNLANVKMHNLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 碳酸丙烯酯 在 IL(OAc^-)-MIL-101-NH₂ 作用下， 以 neat (no solvent) 为溶剂， 反应 9.0h， 以75%的产率得到5-methyl-3-(pyridin-2-yl)oxazolidin-2-one
  参考文献：
  名称：

  Metal–Organic Framework MIL-101-NH₂-Supported Acetate-Based Butylimidazolium Ionic Liquid as a Highly Efficient Heterogeneous Catalyst for the Synthesis of 3-Aryl-2-oxazolidinones

  摘要：

  A novel heterogeneous catalyst, the ionic liquid (IL) of 1-butyl-3-methylimidazolium acetate (BmimOAc) immobilized on MIL-101-NH2, denoted as IL(OAc-)-MIL-101-NH2, was prepared by the "ship-in-a-bottle" strategy. The IL of BmimOAc was prepared in the MIL-101-NH2 nanocages primordially, in which the condensation product of MIL-101-NH2's amine group with 1,1'-carbonyldiimidazole (CDI) reacted with 1-bromo butane, and then the intermediate exchanged with potassium acetate. The structure and physicochemical properties of IL(OAc-)-MIL-101-NH2 were characterized by powder X-ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, DRS UV-vis, nitrogen adsorption-desorption, and elemental analysis. The results indicated that BmimOAc was anchored in the MIL-101-NH2 skeleton via the acylamino group and confined in the nanocages in the form of a single molecule. The composite material of IL(OAc-)-MIL-101-NH2 exhibited excellent catalytic activity and catalytically synthesized 3-aryl-2-oxazolone in an excellent yield of 92%. It can be reused up to six times without noteworthy loss of its activity and demonstrated distinct size-selective property for substrates. It was conjectured that the diffusion kinetics of reactants could be controlled by the aperture size of the metal-organic framework support.

  DOI：

  10.1021/acs.langmuir.8b03153

文献信息

• Bifunctional organocatalysts for the conversion of CO₂, epoxides and aryl amines to 3-aryl-2-oxazolidinones
  作者：Ya-Fei Xie、Cheng Guo、Lei Shi、Bang-Hua Peng、Ning Liu

  DOI：10.1039/c9ob00224c

  日期：——

  3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate

  开发了一种合成3-芳基-2-恶唑烷酮的途径，该途径是通过CO 2，芳基胺和环氧化物之间的三组分反应，以及由有机催化剂和DBU（1,8-二氮杂双环[5.4。 0] undec-7-ene）。该方法允许在温和的反应条件下，广泛的具有各种官能团的环氧化物和芳基胺底物。对照实验表明，通过环氧化物与CO 2的环加成反应形成环状碳酸酯，其进一步与源自环氧化物和芳基胺的β-氨基醇反应，最终形成3-芳基-2-恶唑烷酮。