N-[[(5S)-3-[3-fluoro-4-[4-(2-phenylmethoxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide | 174649-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-[[(5S)-3-[3-fluoro-4-[4-(2-phenylmethoxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 174649-08-2
• 化学式: C₂₅H₂₉FN₄O₅
• 分子量: 484.527
• InChiKey: SOHOVZJKUUPWIY-NRFANRHFSA-N

物化性质

• 沸点：
  732.0±60.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[[(5S)-3-[3-fluoro-4-[4-(2-phenylmethoxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以89%的产率得到N-[[(5S)-3-[3-氟-4-[4-(2-羟基乙酰基)-1-哌嗪基]苯基]-2-氧代-5-噁唑烷基]甲基]-乙酰胺
  参考文献：
  名称：

  通过TMSN 3的对映选择性催化开环动态分解环氧氯丙烷。芳基恶唑烷酮抗菌剂的实用合成

  摘要：

  通过（salen）Cr（III）N 3络合物1催化的TMSN 3对映选择性不对称开环，实现了外消旋环氧氯丙烷的动力学动力学拆分。以高对映体纯度获得所得的3-叠氮基-1-氯-2-三甲基甲硅烷氧基丙烷产物，并将其掺入U-100592的合成中，U-100592是一类高度有前景的芳基恶唑烷酮抗菌剂的代表。

  DOI：

  10.1016/0040-4039(96)01835-7
• 作为产物：
  描述：

  N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline 在 palladium on activated charcoal 吡啶 、 正丁基锂 、 二氯甲烷 、 氢气 、 三乙胺 、 甲胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 68.0h， 生成 N-[[(5S)-3-[3-fluoro-4-[4-(2-phenylmethoxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of U-100592 and U-100766, Two Oxazolidinone Antibacterial Agents for the Potential Treatment of Multidrug-Resistant Gram-Positive Bacterial Infections

  摘要：

  Bacterial resistance development has become a very serious clinical problem for many classes of antibiotics. The 3-aryl-2-oxazolidinones are a relatively new class of synthetic antibacterial agents, having a new mechanism of action which involves very early inhibition of bacterial protein synthesis. We have prepared two potent, synthetic oxazolidinones, U-100592 and U-100766, which are currently in clinical development for the treatment of serious multidrug-resistant Gram-positive bacterial infections caused by strains of staphylococci, streptococci, and enterococci. The in vitro and in vivo (po and iv) activities of U-100592 and U-100766 against representative strains are similar to those of vancomycin. U-100592 and U-100766 demonstrate potent in vitro activity against Mycobacterium tuberculosis. A novel and practical asymmetric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for the synthesis of U-100592 and U-100766. This involves the reaction of N-lithioarylcarbamates with (R)-glycidyl butyrate, resulting in excellent yields and high enantiomeric purity of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones,

  DOI：

  10.1021/jm9509556

文献信息

• Short and practical enantioselective synthesis of linezolid and eperezolid via proline-catalyzed asymmetric α-aminooxylation
  作者：Srinivasarao V. Narina、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2006.07.065

  日期：2006.9

  An efficient enantioselective synthesis of the antibacterials, linezolid (U-100766), and eperezolid (U-100592) using D-proline-catalyzed asymmetric alpha-aminooxylation of aldehydes as the key step is described here. This is the first report on the enantioselective synthesis of linezolid and eperezolid using asymmetric catalysis. (c) 2006 Elsevier Ltd. All rights reserved.
• J. Med. Chem. 1996, 39, 673-679
  作者：

  DOI：——

  日期：——
• Heteroatom Chemistry. 2008, 19, 316-319
  作者：

  DOI：——

  日期：——
• Tetrahedron Lett. 1999, 40, 4855-4856
  作者：

  DOI：——

  日期：——
• Tetrahedron Lett. 1996, 37, 7937-7940
  作者：

  DOI：——

  日期：——