3-(thiophen-2-yl)oxazolidine-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: 3-(thiophen-2-yl)oxazolidine-2-one
• 英文别名: 3-(thiophen-2-yl)oxazolidin-2-one；Thienyloxazolidinone；3-thiophen-2-yl-1,3-oxazolidin-2-one
• 化学式: C₇H₇NO₂S
• 分子量: 169.204
• InChiKey: SMBYBBGILNRWNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(thiophen-2-yl)oxazolidine-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以64%的产率得到3-(thiophen-2-yl)oxazolidine-2-thione
  参考文献：
  名称：

  钌催化的O到S烷基的迁移：伪可逆的Barton–McCombie途径

  摘要：

  实际的钌催化的O-至S-烷基迁移可提供优异产率的结构多样的硫代恶唑烷酮。我们的研究表明，这种催化转化是通过伪可逆自由基途径进行的，该途径与经典的Barton-McCombie反应具有相似的机理。

  DOI：

  10.1002/anie.201505280
• 作为产物：
  描述：

  2-碘噻吩 、 2-唑烷酮 在 potassium phosphate 、 copper(l) iodide 、 乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以59%的产率得到3-(thiophen-2-yl)oxazolidine-2-one
  参考文献：
  名称：

  在乙二胺存在下铜催化芳基碘与苯甲酰胺或氮杂环的 N-芳基化

  摘要：

  在乙二胺（10 mol％）作为配体和K 3 PO 4 或Cs 2 CO 3 作为碱存在下，用催化CuI（10 mol％）进行铜催化的苯甲酰胺或氮杂环的N-芳基化条件温和。

  DOI：

  10.1055/s-2002-20457

文献信息

• Copper-Catalyzed One-Pot Synthesis of <i>N</i>-Aryl Oxazolidinones from Amino Alcohol Carbamates
  作者：William Mahy、Pawel K. Plucinski、Christopher G. Frost

  DOI：10.1021/ol502322c

  日期：2014.10.3

  sequential intramolecular cyclization of amino alcohol carbamates followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions has been developed. The reaction occurred in good yields and tolerated aryl iodides containing functionalities such as nitriles, ketones, ethers, and halogens. Heteroaryl iodides and substituted amino alcohol carbamates were also well tolerated.

  已经开发出在氨基甲酸酯氨基甲酸酯的有效顺序分子内环化，然后在温和条件下与芳基碘化物进行铜催化的交叉偶联。该反应以高收率进行，并且可以耐受含有官能团（例如腈，酮，醚和卤素）的芳基碘化物。杂芳基碘化物和取代的氨基醇氨基甲酸酯也被很好地耐受。
• Oxazolidinone combinatorial libraries, compositions and methods of preparation
  申请人：——

  公开号：US20020183371A1

  公开（公告）日：2002-12-05

  Oxazolidinones and methods for their synthesis are provided. Also provided are combinatorial libraries comprising oxazolidinones, and methods to prepare the libraries. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. The methods of library preparation include the attachment of oxazolidinones to a solid support. The methods of compound preparation in one embodiment involve the reaction of an iminophosphorane with a carbonyl containing polymeric support.

  本发明提供了噁唑烷酮及其合成方法。还提供了包含噁唑烷酮的组合式文库以及制备这些文库的方法。此外，还提供了制备生物活性噁唑烷酮以及包含这些噁唑烷酮的药用组合物的方法。文库制备方法包括将噁唑烷酮附着到固体支持上。在一种实施例中，化合物制备方法涉及使用亚胺磷酰胺与含羰基的聚合物支持物反应。
• COMPOUNDS AND COMPOSITIONS AS INHIBITORS OF CANNABINOID RECEPTOR 1 ACTIVITY
  申请人：Liu Hong

  公开号：US20100234365A1

  公开（公告）日：2010-09-16

  The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of Cannabinoid Receptor 1 (CB1).

  本发明提供了化合物、包含这些化合物的制药组合物以及使用这些化合物治疗或预防与大麻素受体1（CB1）活性相关的疾病或障碍的方法。
• 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.
• CuI/N,N-dimethylglycine-catalyzed synthesis of N-aryloxazolidinones from aryl bromides
  作者：Jiaojiao Li、Yihua Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1016/j.tetlet.2012.05.081

  日期：2012.8

  CuI/N,N-dimethylglycine catalyzed coupling of aryl bromides with substituted oxazolidinones took place at 120 degrees C in DMF, affording the corresponding N-arylation products with good to excellent yields. A number of functional groups, such as ketone, nitrile, nitro, methoxy, and hydroxyl were tolerated under these conditions, thereby allowing diversity synthesis of N-aryloxazolidinones. (C) 2012 Elsevier Ltd. All rights reserved.