3-(3-chlorophenyl)oxazolidin-2-one | 2033-32-1

• 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-(3-chlorophenyl)oxazolidin-2-one
• 英文别名: 3-(3-chlorophenyl)-1,3-oxazolidin-2-one
• CAS: 2033-32-1
• 化学式: C₉H₈ClNO₂
• 分子量: 197.621
• InChiKey: CJAHEQXHVWLBJN-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  304.0±21.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-chlorophenyl)oxazolidin-2-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(3-氯苯胺基)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：

  3-氯苯胺 在 1-丁基-3-甲基咪唑溴盐 、 1-丁基-3-甲基咪唑乙酸盐 作用下， 反应 1.0h， 生成 3-(3-chlorophenyl)oxazolidin-2-one
  参考文献：
  名称：

  BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

  摘要：

  An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. H-1 NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.07.034

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。
• One-Pot Conversion of Carbon Dioxide, Ethylene Oxide, and Amines to 3-Aryl-2-oxazolidinones Catalyzed with Binary Ionic Liquids
  作者：Binshen Wang、Elnazeer H. M. Elageed、Dawei Zhang、Sijuan Yang、Shi Wu、Guirong Zhang、Guohua Gao

  DOI：10.1002/cctc.201300801

  日期：2014.1

  An effective one‐pot method for the conversion of carbon dioxide, ethylene oxide, and amines to 3‐aryl‐2‐oxazolidinones has been developed. This one‐pot method consists of two parallel reactions and a subsequent cascade reaction between the two products of the corresponding parallel reactions. Notably, the binary ionic liquids of 1‐butyl‐3‐methyl‐imidazolium bromide and 1‐butyl‐3‐methyl‐imidazolium

  已开发出一种有效的一锅法，可将二氧化碳，环氧乙烷和胺转化为3-芳基-2-恶唑烷酮。这种单锅法由两个平行反应和相应平行反应的两个产物之间的随后级联反应组成。值得注意的是，溴化1-丁基-3-甲基咪唑鎓和乙酸1-丁基-3-甲基咪唑鎓的二元离子液体对这种新策略显示出协同的催化作用。由于溴的良好亲核性和离去能力，溴化1-丁基-3-甲基咪唑鎓在两个平行反应中必不可少，而乙酸1-丁基-3-甲基咪唑鎓乙酸酯由于随后的级联反应在随后的级联反应中起主要作用。醋酸盐的强碱性。此外，二元离子液体可以使用三次，而不会显着降低催化活性。
• <i>para</i> ‐Selective Palladium‐Catalyzed C−H Difluoroalkylation by Weak Oxazolidinone Assistance
  作者：Xinyue Fang、Yuqiang Tan、Linghui Gu、Lutz Ackermann、Wenbo Ma

  DOI：10.1002/cctc.202002056

  日期：2021.4.9

  Herein, we report a general and efficient method for the palladium‐catalyzed remote C(sp2)−H difluoroalkylation of N‐aryloxazolidinone derivatives with commercially available difluoroalkyl bromide. This method tolerates a wide range of functional groups with 26 examples in up to 96 % yields. Moreover, it proceeds with complete para‐selectivity. Preliminary mechanistic studies indicated that a single

  在本文中，我们报告了一种通用有效的方法，用于将N-芳基恶唑烷酮衍生物与市售的二氟烷基溴化物进行钯催化的远程C（sp 2）-H二氟烷基化。该方法可耐受26个实例的各种官能团，产率最高可达96％。而且，它具有完全的对位选择性。初步的机理研究表明，单个电子转移过程可能参与了这种转变。