3-isobutyl-4-phenyloxazolidin-2-one | 1204247-91-5

• 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: 3-isobutyl-4-phenyloxazolidin-2-one
• CAS: 1204247-91-5
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: SFPGBCMDQPITIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯乙烯 在 L-脯氨酸 作用下， 以 水 、 乙腈 为溶剂， 20.0~110.0 ℃ 、6.0 MPa 条件下， 反应 12.17h， 生成 3-isobutyl-4-phenyloxazolidin-2-one 、 3-isobutyl-5-phenyloxazolidin-2-one
  参考文献：
  名称：

  Proline-Catalyzed Synthesis of 5-Aryl-2-oxazolidinones from Carbon Dioxide and Aziridines Under Solvent-Free Conditions

  摘要：

  Natural alpha-amino acids were proven to be ecofriendly and recyclable catalysts for the carboxylation of aziridines with CO2 without utilization of any organic solvents or additives. Notably, a series of 5-aryl-2-oxazolidinones were obtained in good yield together with excellent chemo- and regioselectivity under mild conditions using proline as the catalyst. Notably, the catalyst could be recycled more than five times after a simple separation procedure without appreciable loss of catalytic activity. This process represents a promising strategy for homogeneous catalyst recycling.

  DOI：

  10.1080/00397911.2010.521903

文献信息

• Ruthenium Porphyrin Catalyzed Synthesis of Oxazolidin‐2‐ones by Cycloaddition of CO ₂ to Aziridines
  作者：Daniela Carminati、Emma Gallo、Caterina Damiano、Alessandro Caselli、Daniela Intrieri

  DOI：10.1002/ejic.201801208

  日期：2018.12.31

  efficiently promoted by ruthenium(VI) imidoporphyrin complexes and yields a mixture of 5‐aryl (A) and 4‐aryl (B) substituted oxazolidin‐2‐ones with a regioisomeric A/B ratio up to 99:1. Several oxazolidin‐2‐one molecules were synthesized at 100 °C and 0.6 MPa of carbon dioxide by using the low catalytic loading of 1 mol‐%. The formation of a deactivated compound, deriving from the ruthenium catalyst, suggested

  钌（VI）亚氨基卟啉配合物可有效促进N-取代-2-芳基氮丙啶与CO 2的反应，生成5-芳基（A）和4-芳基（B）取代的恶唑烷二-2-酮与区域异构体的混合物A / B比例高达99：1。通过使用1 mol％的低催化负载量，在100°C和0.6 MPa的二氧化碳条件下，合成了几个恶唑烷-2-酮分子。衍生自钌催化剂的失活化合物的形成表明亚氨基氮原子可能具有催化作用。
• Zirconyl chloride: an efficient recyclable catalyst for synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions
  作者：Ying Wu、Liang-Nian He、Ya Du、Jin-Quan Wang、Cheng-Xia Miao、Wei Li

  DOI：10.1016/j.tet.2009.05.034

  日期：2009.8

  Zirconyl chloride was found to be an efficient catalyst for the cycloaddition reaction of aziridines with CO2, thus leading to the preferential formation of 5-aryl-2-oxazolidinones under solvent-free conditions. The methodology could be extended to various substituted aziridines with high conversion and chemo-, regio-, and stereoselectivity. Furthermore, the catalyst could be reused over five times

  发现氧化锆氯化物是氮丙啶与CO 2的环加成反应的有效催化剂，因此导致在无溶剂条件下优先形成5-芳基-2-恶唑烷酮。该方法可以扩展到具有高转化率和化学，区域和立体选择性的各种取代的氮丙啶。此外，该催化剂可以重复使用五次，而不会显着降低活性。有趣的是，回收的催化剂与新鲜催化剂相比显示出更高的活性，大概是由于其形态变化。这种廉价且水分稳定的催化剂的使用使该方案实用，对环境无害且在经济上具有吸引力。
• Quaternary Ammonium Bromide Functionalized Polyethylene Glycol: A Highly Efficient and Recyclable Catalyst for Selective Synthesis of 5-Aryl-2-oxazolidinones from Carbon Dioxide and Aziridines Under Solvent-Free Conditions
  作者：Ya Du、Ying Wu、An-Hua Liu、Liang-Nian He

  DOI：10.1021/jo800269v

  日期：2008.6.1

  A quaternary ammonium bromide covalently bound to polyethylene glycol (PEG, MW = 6000), i.e., PEG(6000)-(NBu3Br)(2), was found to be an efficient and recyclable catalyst for the cycloaddition reaction of aziridines to CO2 under mild conditions without utilization of additional organic solvents or cocatalysts. As a result, 5-aryl-2-oxazolidinone was obtained in high yield with excellent regioselectivity. The catalyst worked well for a wide variety of 1-alkyl-2-arylaziridines. Besides, the catalyst could be recovered by centrifugation and reused without significant loss of catalytic activity and selectivity.