5-(4-fluorophenyl)-1,3-oxazolidin-2-one | 19338-43-3

• 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: 5-(4-fluorophenyl)-1,3-oxazolidin-2-one
• 英文别名: 5-(4-fluorophenyl)oxazolidin-2-one；5-(4-fluoro-phenyl)-oxazolidin-2-one；5--oxazolidon-(2)；5-(4-Fluorphenyl)-2-oxazolidon
• CAS: 19338-43-3
• 化学式: C₉H₈FNO₂
• 分子量: 181.166
• InChiKey: JAVVBBLOGSHTRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenyl)-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 生成 1-(p-Fluor-phenyl)-2-methylamino-aethanol
  参考文献：
  名称：

  一些肾上腺素类似物。

  摘要：

  DOI：

  10.1021/jm00312a004
• 作为产物：
  描述：

  [2-(4-氟-苯基)-2-氧代-乙基]-氨基甲酸叔丁酯 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 5-(4-fluorophenyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Discovery of 3,5-Diphenyl-4-methyl-1,3-oxazolidin-2-ones as Novel, Potent, and Orally Available Δ-5 Desaturase (D5D) Inhibitors

  摘要：

  The discovery and optimization of Delta-5 desaturase (D5D) inhibitors are described. Investigation of the 1,3-oxazolidin-2-one scaffold was inspired by a pharmacophore model constructed from the common features of several hit compounds, resulting in the identification of 3,5-diphenyl-1,3-oxazolidin-2-one Sh as a novel lead showing potent in vitro activity. Subsequent optimization focused on the modification of two metabolic sites, which provided (4S,5S)-5i, a derivative with improved metabolic stability. Moreover, adding a substituent into the upper phenyl moiety further enhanced the intrinsic activity, which led to the discovery of 5-[(4S,5S)-5-(4fluorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]benzene-1,3-clicarbonitrile (4S,5S)-5n, endowed with excellent DSD binding affinity, cellular activity, and high oral bioavailability in a mouse. It exhibited robust in vivo hepatic arachidonic acid/dihomo-gamma-linolenic acid ratio reduction (a target engagement marker) in an atherosclerosis mouse model. Finally, an asymmetric synthetic procedure for this compound was established.

  DOI：

  10.1021/acs.jmedchem.7b01210

文献信息

• Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide
  作者：Giulio Bresciani、Marco Bortoluzzi、Guido Pampaloni、Fabio Marchetti

  DOI：10.1039/d1ob00458a

  日期：——

  dioxide, highlighting the superior activity of [NH2Et2]I. Then, working at room temperature, atmospheric CO2 pressure and in the absence of solvent, the [NH2Et2]I-catalyzed synthesis of a series of 5-aryl-2-oxazolidinones was accomplished in good to high yields and excellent selectivity, from 2-aryl-aziridines with N-methyl or N-ethyl groups. NMR studies and DFT calculations outlined the pivotal role of

  在模型氮丙啶与二氧化碳的偶联反应中探索了卤化铵盐的催化潜力，突出了 [NH 2 Et 2 ]I 的优越活性。然后，在室温、大气 CO 2压力和无溶剂条件下，[NH 2 Et 2 ]I 催化合成一系列 5-aryl-2-oxazolidinones 以良好至高产率和优异的选择性完成, 来自具有N-甲基或N的 2-芳基-氮丙啶-乙基。NMR 研究和 DFT 计算概述了二乙基铵阳离子和碘化物阴离子的关键作用。所提出的方法代表了一种方便的选择，用于获得有限数量的有价值的分子，即使在最近几年也已经报道了更复杂和更昂贵的催化系统。
• Regioselective Ring‐Opening of Styrene Oxide Derivatives Using Halohydrin Dehalogenase for Synthesis of 4‐Aryloxazolidinones
  作者：Nanwei Wan、Jiawei Tian、Xiaoying Zhou、Huihui Wang、Baodong Cui、Wenyong Han、Yongzheng Chen

  DOI：10.1002/adsc.201900786

  日期：2019.10.22

  A biocatalytic approach towards a range of 4‐aryloxazolidinones is developed using a halohydrin dehalogenase from Ilumatobacter coccineus (HheG) as biocatalyst. The method is based on the HheG‐catalyzed α‐position regioselective ring‐opening of styrene oxide derivatives with cyanate as a nucleophile, producing the corresponding 4‐aryloxazolidinones in moderate to good yields. Synthesis of enantiopure

  使用来自球菌Ilumatobacter coccineus（HheG）的卤代醇脱卤酶作为生物催化剂，开发了一种针对一系列4-芳基恶唑烷酮的生物催化方法。该方法基于以氰酸酯为亲核试剂的苯乙烯氧化物衍生物的HheG催化的α位置区域选择性开环，以中等至良好的产率产生相应的4-芳基恶唑烷酮。使用手性环氧材料也可以合成对映体纯的4-芳基恶唑烷酮。
• Oxazolidinone Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators
  申请人：Slassi Abdelmalik

  公开号：US20090012089A1

  公开（公告）日：2009-01-08

  The present invention is directed to compounds of Formula I: Wherein R 1 , R 2 , Y, m and n are further defined in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

  本发明涉及式I的化合物：其中R1、R2、Y、m和n在描述中进一步定义。本发明还涉及制备该化合物的过程，以及用于制备的新中间体，包含该化合物的药物组合物，以及该化合物在治疗中的使用。
• Oxazolidinone compounds and their use as metabotropic glutamate receptor potentiators
  申请人：Slassi Abdelmalik

  公开号：US20070275966A1

  公开（公告）日：2007-11-29

  The present invention is directed to compounds of Formula I: Wherein R 1 , R 2 , Y, m and n are further defined in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

  本发明涉及公式I的化合物：其中R1、R2、Y、m和n在描述中进一步定义。本发明还涉及制备该化合物的过程，以及用于制备的新中间体，包含该化合物的制药组合物，以及该化合物在治疗中的使用。
• Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide
  作者：Jef R. Vanhoof、Robin Dirix、Dirk E. De Vos

  DOI：10.1039/d2gc03879j

  日期：——

  olefins with NH3 and CO2 or CS2 in a telescoped sequence is reported, forming 2-oxazolidinones or 2-thiazolidinethiones. The reaction proceeds via a N–H aziridine, which subsequently undergoes ring expansion with CO2 or CS2. Both steps are mediated by the same simple iodide catalyst and total yields of up to 91% referring to the alkene are achieved with excellent regioselectivities. This sustainable

  N-杂环是在有机合成和应用中经常出现的重要结构基序。因此，非常需要使用烯烃等常见起始原料的直接和绿色合成方法。在此，报道了芳香族烯烃与 NH 3和 CO 2或 CS 2以伸缩序列进行无金属电化学偶联，形成 2-恶唑烷酮或 ​​2-噻唑烷硫酮。该反应通过N-H 氮丙啶进行，随后与 CO 2或 CS 2发生扩环. 这两个步骤均由相同的简单碘化物催化剂介导，并且以出色的区域选择性实现了高达 91% 的烯烃总收率。这种使用现成材料的可持续反应具有出色的原子效率，只有 H 2作为潜在有用的副产物。