5-tetrahydro-2H-2-pyranyloxymethyl-2-oxazolidinone | 513068-35-4

• 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: 5-tetrahydro-2H-2-pyranyloxymethyl-2-oxazolidinone
• 英文别名: 5-tetrahydro-2H-2-pyranyloxymethyl oxazolidin-2-one；5-(Oxan-2-yloxymethyl)-1,3-oxazolidin-2-one
• CAS: 513068-35-4
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: DTUQLFHOLZZAEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴甲基苯 、 5-tetrahydro-2H-2-pyranyloxymethyl-2-oxazolidinone 在 copper(l) iodide 、 (1S,2S)-(+)-1,2-环己二胺 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以50%的产率得到3-{3-methylphenyl}-5-(tetrahydro-2H-2-pyranyloxy-methyl)-2-oxazolidinone
  参考文献：
  名称：

  Highly Efficient CuI-Catalyzed Coupling of Aryl Bromides with Oxazolidinones Using Buchwald's Protocol:  A Short Route to Linezolid and Toloxatone

  摘要：

  [GRAPHICS]Coupling of a variety of substituted aryl bromides with oxazolidinones has been achieved using the Buchwald protocol for the amidation of aryl halides. This procedure is exemplified by the synthesis of two medicinally important molecules, linezolid and toloxatone.

  DOI：

  10.1021/ol026902h
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 5-羟甲基噁唑烷-2-酮 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 5-tetrahydro-2H-2-pyranyloxymethyl-2-oxazolidinone
  参考文献：
  名称：

  Highly Efficient CuI-Catalyzed Coupling of Aryl Bromides with Oxazolidinones Using Buchwald's Protocol:  A Short Route to Linezolid and Toloxatone

  摘要：

  [GRAPHICS]Coupling of a variety of substituted aryl bromides with oxazolidinones has been achieved using the Buchwald protocol for the amidation of aryl halides. This procedure is exemplified by the synthesis of two medicinally important molecules, linezolid and toloxatone.

  DOI：

  10.1021/ol026902h

文献信息

• [EN] IMPROVED PROCESSES FOR THE PREPARATION OF LINEZOLID USING NOVEL INTERMEDIATES<br/>[FR] PROCÉDÉS AMÉLIORÉS POUR LA PRÉPARATION DE LINÉZOLIDE PAR UTILISATION DE NOUVEAUX INTERMÉDIAIRES
  申请人：SYMED LABS LTD

  公开号：WO2014174522A1

  公开（公告）日：2014-10-30

  Provided herein are improved, commercially viable and industrially advantageous processes for the preparation of Linezolid, in high yield and purity, using novel intermediates. In one aspect, provided herein are efficient, industrially advantageous and environmentally friendly processes for the preparation of linezolid, in high yield and with high purity, using novel intermediates. The processes disclosed herein avoid the tedious and cumbersome procedures of the prior processes, thereby resolving the problems associated with the processes described in the prior art, which is more convenient to operate at lab scale and in commercial scale operations.

  本文提供了一种改进的、商业可行的、在工业上具有优势的利用新型中间体制备利奈唑胺的工艺，产率高，纯度高。在一个方面，本文提供了一种高效、在工业上具有优势且环保的利用新型中间体制备利奈唑胺的工艺，产率高，纯度高。本文披露的工艺避免了先前工艺中繁琐和繁重的程序，从而解决了与先前技术描述的工艺相关的问题，更方便在实验室规模和商业规模操作中进行操作。
• [EN] IMPROVED PROCESS FOR THE PREPARATION OF LINEZOLID INTERMEDIATE<br/>[FR] PROCÉDÉ AMÉLIORÉ POUR LA PRÉPARATION D'UN INTERMÉDIAIRE DE LINÉZOLIDE
  申请人：SYMED LABS LTD

  公开号：WO2014045292A1

  公开（公告）日：2014-03-27

  The present inventors have surprisingly found that (5R)-5-(hydroxymethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone can be prepared in high purity and with high yield, by reacting 3-fluoro-4-morpholinyl aniline with (R)-glycidol, or an ester or an ether derivative thereof, to produce a novel 2-hydroxypropyl intermediate, which is then subjected cyclization using a suitable reagent to produce (5R)-5-(hydroxymethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone or an ester, or an ether derivative thereof. In one aspect, provided herein are efficient, industrially advantageous and environmentally friendly processes for the preparation of (5R)-5-(hydroxymethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone and its derivatives, in high yield and with high purity, using novel intermediates.

  本发明人惊奇地发现，通过将3-氟-4-吗啡基苯胺与(R)-环氧丙醇或其酯或醚衍生物反应，制备出一种新型2-羟基丙醇中间体，然后使用适当的试剂进行环化反应，可以高纯度高产率地制备出(5R)-5-(羟甲基)-3-[3-氟-4-(4-吗啡基)苯基]-2-噁唑烷酮或其酯或醚衍生物。在一个方面，本文提供了高效、工业上有利和环保的过程，使用新型中间体高产率高纯度地制备(5R)-5-(羟甲基)-3-[3-氟-4-(4-吗啡基)苯基]-2-噁唑烷酮及其衍生物。
• IMPROVED PROCESSES FOR THE PREPARATION OF LINEZOLID USING NOVEL INTERMEDIATES
  申请人：SYMED LABS LIMITED

  公开号：US20160102064A1

  公开（公告）日：2016-04-14

  Provided herein are improved, commercially viable and industrially advantageous processes for the preparation of Linezolid, in high yield and purity, using novel intermediates. In one aspect, provided herein are efficient, industrially advantageous and environmentally friendly processes for the preparation of linezolid, in high yield and with high purity, using novel intermediates. The processes disclosed herein avoid the tedious and cumbersome procedures of the prior processes, thereby resolving the problems associated with the processes described in the prior art, which is more convenient to operate at lab scale and in commercial scale operations.

  本文提供了一种改进的、商业可行的、工业上优越的过程，用于使用新型中间体高产高纯度制备Linezolid。在一个方面，本文提供了一种高效、工业优越、环境友好的过程，用于使用新型中间体高产高纯度制备Linezolid。本文所披露的过程避免了先前过程的繁琐和麻烦程序，从而解决了与先前技术描述的过程相关的问题，更方便地在实验室规模和商业规模操作。
• General cross-coupling reactions with adaptive dynamic homogeneous catalysis
  作者：Indrajit Ghosh、Nikita Shlapakov、Tobias A. Karl、Jonas Düker、Maksim Nikitin、Julia V. Burykina、Valentine P. Ananikov、Burkhard König

  DOI：10.1038/s41586-023-06087-4

  日期：——

  (AD-HoC) with nickel under visible-light-driven redox reaction conditions for general C(sp2)–(hetero)atom coupling reactions. The self-adjustive nature of the catalytic system allowed the simple classification of dozens of various classes of nucleophiles in cross-coupling reactions. This is synthetically demonstrated in nine different bond-forming reactions (in this case, C(sp2)–S, Se, N, P, B, O, C(sp3, sp2

  交叉偶联反应是现代有机合成中最重要的转化之一1,2,3。尽管考虑到各种方案，报道的（杂）芳基卤化物和亲核试剂偶联配偶体的范围非常大，但化合物类别之间的反应条件差异很大，因此需要根据具体情况重新优化反应条件4。在这里，我们介绍了在可见光驱动的氧化还原反应条件下镍的自适应动态均相催化（AD-HoC），用于一般的 C( sp 2 )–(杂)原子偶联反应。催化系统的自我调节性质允许在交叉偶联反应中对数十种不同类别的亲核试剂进行简单分类。这在九种不同的成键反应（在本例中为 C( sp 2 )–S、Se、N、P、B、O、C( sp 3、  sp 2、  sp )、Si、Cl）中得到了综合证明在可预测的反应条件下进行数百个合成实例。催化反应中心和条件因添加的亲核试剂或如果需要而添加市售的廉价胺碱而彼此不同。
• US9586913B2
  申请人：——

  公开号：US9586913B2

  公开（公告）日：2017-03-07