3-(2-methoxyphenyl)oxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-methoxyphenyl)oxazolidin-2-one
• 英文别名: 3-(2-methoxyphenyl)-1,3-oxazolidin-2-one
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: MGJWSVZKANGOCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyphenyl)oxazolidin-2-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-[(2-甲氧基苯基)氨基]乙醇
  参考文献：
  名称：

  Bis-aryl Urea Derivatives as Potent and Selective LIM Kinase (Limk) Inhibitors

  摘要：

  The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 mu M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 mu M inhibited only Limk1 and STK16 with >= 80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

  DOI：

  10.1021/jm501680m
• 作为产物：
  描述：

  2-唑烷酮 、 2-碘苯甲醚 在 potassium phosphate 、 copper(l) iodide 、 (+/-)-trans-cyclohexanediamine 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以93%的产率得到3-(2-methoxyphenyl)oxazolidin-2-one
  参考文献：
  名称：

  Copper-catalyzed N-Arylation of 2-Oxazolidinones. An Expeditious Route to Toloxatone

  摘要：

  3-Aryl-2-oxazolidinones are obtained in excellent yields through the copper-catalyzed N-arylation of 2-oxazolidinones with a variety of aryl iodides. With aryl halides containing both iodo and bromo substituents, a high C-I/C-Br selectivity can be achieved. The procedure has been successfully applied to the preparation of a key intermediate in the synthesis of linezolid and to develop an expeditious route to toloxatone.

  DOI：

  10.3987/com-03-s7

文献信息

• Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide
  作者：Congmin Mei、Yibo Zhao、Qianwei Chen、Changsheng Cao、Guangsheng Pang、Yanhui Shi

  DOI：10.1002/cctc.201800142

  日期：2018.7.19

  three‐component fixation of atmospheric CO2 with readily available 1,2‐dichloroethane and aromatic amine toward oxazolidinones catalyzed by in situ NHC was developed. The reaction occurred in good to excellent yields with good generality and wide functional group tolerance, including challenging steric hindered substituted‐dichloroethane (e.g. 1,2‐dichloropropane and 2,3‐dichlorobutane). The catalytic system

  已经开发了一种有效的三组分固定方法，用现成的NHC催化的1,2-二氯乙烷和芳香族胺直接固定在恶唑烷酮上，以固定大气中的CO 2。该反应以良好的通用性和宽泛的官能团耐受性（包括具有挑战性的位阻取代的二氯乙烷（例如1,2-二氯丙烷和2,3-二氯丁烷））以良好的收率获得了良好的收率。该催化体系对空气和湿气不敏感，即使在约0.3atm的二氧化碳压力下也可获得高产率的恶唑烷酮。机理研究表明，该反应是通过NHC-CO 2原位催化NHC催化的加合物中，1-丁基-3-甲基咪唑-2-羧酸盐为中间体，而氨基氯化物参与反应路径。催化剂可以循环使用至少3次而不会明显降低催化活性。该协议还可以有效地制备六元3-芳基-1,3-氧杂嗪酮-2-一，甚至七元3-芳基-1,3-氧杂氮杂-2-酮，当1,3-二氯丙烷和1时使用了4-二氯丁烷。
• A One-Pot Synthesis of <i>N</i> -Aryl-2-Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes
  作者：Teemu Niemi、Jesus E. Perea-Buceta、Israel Fernández、Otto-Matti Hiltunen、Vili Salo、Sari Rautiainen、Minna T. Räisänen、Timo Repo

  DOI：10.1002/chem.201602338

  日期：2016.7.18

  catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional‐group tolerance under ambient CO2 pressure and mild temperature. This report also provides the first proof‐of‐principle for the single‐operation synthesis of elusive seven‐membered ring cyclic urethanes.

  描述了通过将二氧化碳直接插入容易获得的苯胺和二溴代烷烃中的，具有药学意义的N-芳基-恶唑烷酮的多组分组装方法。添加催化量的有机超碱（如Barton碱）可使该转化在环境CO 2压力和温和温度下以高收率和出色的底物官能团耐受性进行。该报告还为难以捉摸的七元环环状氨基甲酸酯的单操作合成提供了第一个原理证明。
• Synthesis of N-aryl-2-oxazolidinones from cyclic carbonates and aromatic amines catalyzed by bio-catalyst
  作者：Congmin Mei、Yibo Zhao、Ke Zou、Changsheng Cao、Guangsheng Pang、Yanhui Shi

  DOI：10.1007/s11164-017-3222-y

  日期：2018.3

  A convenient and effective method of synthesizing 3-aryl-2-oxazolidinones from cyclic carbonates and aryl amines catalyzed by bio-catalyst adenine in the presence of Et3N under solvent-free conditions is described. The protocol is suitable for the wide scope of substrates, e.g. cyclic carbonates with or without substitutes, and aryl amines with either electron-withdrawing or electron-donating group

  描述了在无溶剂条件下在Et 3 N存在下由生物催化剂腺嘌呤催化的环状碳酸酯和芳基胺合成3-芳基-2-恶唑烷酮的便捷有效方法。该方案适用于多种底物，例如带或不带取代基的环状碳酸酯，以及具有吸电子或供电子基团的芳基胺。即使在位阻情况下，在最佳条件下也能以良好或优异的收率获得产品。研究了反应时间，温度，催化剂用量和原料用量对反应的影响，并探讨了反应机理。
• Novel Syntheses of N-Aryloxazolidin-2-ones via Tandem Reactions of Vinyl Sulfonium Salts
  作者：Jinhua Liu、Tian Xie、Chunsong Xie、Deyu Han

  DOI：10.1055/s-0029-1218284

  日期：2009.12

  An unprecedented and efficient domino reaction of diphenyl vinyl sulfonium salt with carbamates leading to the syntheses of N-aryloxazolidin-2-ones has been developed. The scope of this transformation has been studied and a plausible mechanism has been proposed.

  一种前所未有且高效的多米诺反应已被开发，即二苯乙烯磺铵盐与氨基甲酸酯反应，导致N-芳氧杂环-2-酮的合成。对这一转化的适用范围进行了研究，并提出了一种合理的机制。
• Ruthenium(II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group: Experimental and Computational Insights
  作者：Jamie A. Leitch、Philippe B. Wilson、Claire L. McMullin、Mary F. Mahon、Yunas Bhonoah、Ian H. Williams、Christopher G. Frost

  DOI：10.1021/acscatal.6b01370

  日期：2016.8.5

  Herein, we report the ruthenium-catalyzed ortho C-H alkenylation of a wide range of N-aryloxazolidinone scaffolds. Alkenylation was achieved with complete mono selectivity with a scope of 27 examples in 2-MeTHF. Yields ranged from 23 to 94%, producing highly decorated oxazolidinone scaffolds. A kinetically relevant C-H cleavage was also observed with a kinetic isotope effect (KIE) of similar to 2. Density functional theory calculations provided information about mechanism, detailing the beta-hydride elimination as the most energetically challenging step of 13.5 kcal mol(-1). In-depth computational kinetic studies also predicted a KIE of 2.17 for C-H cleavage and an intrinsic KIE for the reaction of 2.22, in line with the experimentally observed value.