3-isopentyl-5-phenyloxazolidin-2-one | 1032818-01-1

• 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-isopentyl-5-phenyloxazolidin-2-one
• 英文别名: 3-isoamyl-5-phenyloxazolidin-2-one
• CAS: 1032818-01-1
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: LDTJIDCELOFUHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2-bromo-1-phenylethyl)dimethylsulfonium bromide 在 L-脯氨酸 作用下， 以 水 为溶剂， 20.0~110.0 ℃ 、6.0 MPa 条件下， 反应 12.0h， 生成 3-isopentyl-5-phenyloxazolidin-2-one 、 3-isopentyl-4-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

• Recyclable bifunctional aluminum salen catalyst for CO2 fixation: the efficient formation of five-membered heterocyclic compounds
  作者：Rongchang Luo、Zhi Yang、Wuying Zhang、Xiantai Zhou、Hongbing Ji

  DOI：10.1007/s11426-016-0405-3

  日期：2017.7

  previously. The catalytic activity obtained by these bifunctional catalysts could be superior to those of the binary type catalysts in the formation of five-membered heterocyclic compounds from the cycloaddition reaction of CO2 and three-membered heterocyclic compounds (including terminal epoxides and N-substituted aziridines), presumably due to the distinguished intramolecularly synergistic catalysis

  已经成功制备了由咪唑基离子液体（IL）部分官能化，在3,3'-位置两侧均具有salen配体的各种独特的Al（salen）配合物，而不是熟悉的5,5'-位置先前。在CO 2与三元杂环化合物（包括末端环氧化物和N的环加成反应）形成五元杂环化合物时，这些双官能催化剂获得的催化活性可能优于二元型催化剂。-取代的氮丙啶），大概是由于杰出的分子内协同催化作用，它可能导致在环境条件下进行环加成反应，并保持优异的收率和前所未有的化学或区域选择性。此外，具有最佳催化性能的聚醚基三官能Al（salen）催化剂可再生和重复使用至少八次，而催化活性没有明显降低。最后，动力学研究表明催化剂的结构对催化活性有重要影响，从而提出了可能的反应机理。
• Catalyst-Free Process for the Synthesis of 5-Aryl-2-Oxazolidinones via Cycloaddition Reaction of Aziridines and Carbon Dioxide
  作者：Liang-Nian He、Xiao-Yong Dou、Zhen-Zhen Yang、Jing-Lun Wang

  DOI：10.1055/s-0030-1258510

  日期：2010.9

  A simple approach for facile synthesis of 5-aryl-2-­oxazolidinones in excellent regioselectivity from aziridines under compressed CO2 conditions was developed in the absence of any catalyst and organic solvent. The reaction outcome was found to be tuned by subtly adjusting CO2 pressure. The adduct formed in situ of aziridine and CO2 is assumed to act as a catalyst in this reaction, which was also studied by means of in situ FT-IR technique.

  在没有任何催化剂和有机溶剂的情况下，研究人员开发了一种在压缩二氧化碳条件下从氮丙啶类化合物中以优异的区域选择性简便合成 5-芳基-2-噁唑烷酮的方法。研究发现，反应结果可通过微妙地调节二氧化碳压力来调整。假定氮丙啶和二氧化碳在原位形成的加合物在该反应中起到催化剂的作用，并通过原位傅立叶变换红外技术对其进行了研究。
• A metal-free porphyrin heterogenised onto SBA-15 silica: A performant material for the CO2 cycloaddition to epoxides and aziridines
  作者：Paolo Sonzini、Nicolas Berthet、Caterina Damiano、Véronique Dufaud、Emma Gallo

  DOI：10.1016/j.jcat.2022.08.036

  日期：2022.10

  The covalently heterogenisation of a free-base porphyrin on SBA-15 silica yielded TPPH2@SBA-15 (TPPH2 = tetraphenyl porphyrin), which was very efficient to promote the CO2 cycloaddition to three-membered rings. The TPPH2@SBA-15/TBAX-based catalytic procedure was very general, as revealed by excellent activities registered in the reaction of CO2 with epoxides, N-alkyl and N-aryl aziridines, forming

  游离碱卟啉在 SBA-15 二氧化硅上的共价异质化产生TPPH 2 @SBA-15 ( TPPH 2 = 四苯基卟啉)，这对于促进三元环的 CO 2环加成 非常有效。基于TPPH 2 @SBA-15 /TBAX 的催化过程非常普遍，正如在 CO 2与环氧化物、N-烷基和N-芳基氮丙啶反应形成环状碳酸酯、N-烷基和N-芳基恶唑烷酮，分别。值得注意的是，这是从相应的N-芳基氮丙啶非均相催化合成N-芳基恶唑烷酮的第一个例子。该方法的放大强调了所有三种研究反应的催化性能都保持在克级范围内，为该程序的未来发展铺平了道路。此外，TPPH 2 @SBA-15对几个连续反应的循环是有效的，并且观察到的催化活性与在新鲜材料存在下记录的催化活性非常相似。所有获得的数据都表明催化协议具有出色的可持续性，以设想即将到来的实际应用。
• Valorization of CO ₂ into <i>N</i> ‐alkyl Oxazolidin‐2‐ones Promoted by Metal‐Free Porphyrin/TBACl System: Experimental and Computational Studies
  作者：Caterina Damiano、Paolo Sonzini、Gabriele Manca、Emma Gallo

  DOI：10.1002/ejoc.202100365

  日期：2021.5.20

  AbstractThe cycloaddition of CO2 to N‐alkyl aziridines was efficiently promoted by the convenient TPPH2/TBACl binary catalytic system. The metal‐free procedure was effective for the synthesis of differently substituted N‐alkyl oxazolidin‐2‐ones in yields up to 100 % and excellent regioselectivities (up to 99 %). The mechanism of the reaction was proposed based on a DFT study which indicated the formation of an adduct between TPPH2 and TBACl as the effective catalytic active species.
• 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.