[(5R)-2-氧代-1,3-恶唑烷-5-基]甲基4-甲基苯磺酸盐 | 109794-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [(5R)-2-氧代-1,3-恶唑烷-5-基]甲基4-甲基苯磺酸盐
• 英文名称: (R)-(2-oxo-1,3-oxazolidin-5-yl)methyl 4-methylbenzenesulfonate
• 英文别名: (R)-5-(4-methylphenylsulfonyloxymethyl)-1,3-oxazolidin-2-one；((5R)-2-oxo-1,3-oxazolidin-5-yl)methyl 4-methylbenzenesulfonate；((5R)-2-oxo-1,3-oxazolidin-5-yl)methyl 4methylbenzenesulfonate；((5R)-2-oxo-1,3-oxazolidin-5-yl)methyl4-methylbenzenesulfonate；[(5R)-2-oxo-1,3-oxazolidin-5-yl]methyl 4-methylbenzenesulfonate
• CAS: 109794-69-6
• 化学式: C₁₁H₁₃NO₅S
• 分子量: 271.294
• InChiKey: OCDQYYSOGFFJPA-SECBINFHSA-N

物化性质

• 熔点：
  96-99 °C
• 沸点：
  540.7±19.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(5R)-2-氧代-1,3-恶唑烷-5-基]甲基4-甲基苯磺酸盐 在 氢化钾 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[[(5R)-2-氧代-1,3-恶唑烷-5-基]甲基]异吲哚-1,3-二酮
  参考文献：
  名称：

  Oxazolidinone chemotherapeutic agents

  摘要：

  式(I)的化合物或其治疗上可接受的盐或前药，可用于治疗细菌感染、牛皮癣、关节炎以及化疗引起的毒性。所述的化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法已被披露。

  公开号：

  US06277868B1
• 作为产物：
  描述：

  (5R)-5-(羟甲基)-1,3-恶唑烷-2-酮 、 对甲苯磺酰氯 在 吡啶 作用下， 生成 [(5R)-2-氧代-1,3-恶唑烷-5-基]甲基4-甲基苯磺酸盐
  参考文献：
  名称：

  通过钯催化的交叉偶联反应合成N-芳基化的恶唑烷酮。在抗菌剂Dup-721的合成中的应用

  摘要：

  描述了用于芳基溴化物和恶唑烷酮的分子间偶联的方法。描述了对可用于制备已知种类的抗菌剂和合成已知的抗菌恶唑烷酮Dup-721的中间体的应用。

  DOI：

  10.1016/s0040-4039(01)00559-7

文献信息

• OXAZOLIDINONE CHEMOTHERAPEUTIC AGENTS
  申请人：——

  公开号：US20020045625A1

  公开（公告）日：2002-04-18

  Compounds of the formula 1 or therapeutically acceptable salts or prodrugs thereof, are useful for treating bacterial infections, psoriasis, arthritis, and toxicity due to chemotherapy. Preparation of the compounds, compositions containing the compounds, and treatment of diseases using the compounds are disclosed.

  该式化合物或其治疗上可接受的盐或前药，可用于治疗细菌感染、牛皮癣、关节炎以及化疗引起的毒性。该化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法已被披露。
• The synthesis and biological evaluation of a novel series of antimicrobials of the oxazolidinone class
  作者：Richard J. Sciotti、Marina Pliushchev、Paul E. Wiedeman、Darlene Balli、Robert Flamm、Angela M. Nilius、Kennan Marsh、DeAnne Stolarik、Robert Jolly、Roger Ulrich、Stevan W. Djuric∗

  DOI：10.1016/s0960-894x(02)00352-9

  日期：2002.8

  A novel series of antimicrobials of the oxazolidinone class is disclosed. These compounds are characterized relative to previously described analogues by a 'halostilbene-derived' pharmacophore and demonstrate enhanced antimicrobial activity against key Gram-positive pathogens when compared to Linezolid. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB
  作者：Ahmed Kamal、G.B. Ramesh Khanna、T. Krishnaji、R. Ramu

  DOI：10.1016/j.tetasy.2006.04.019

  日期：2006.4

  Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified ceramic particles (PS-C) in diisopropyl ether gave the best results. The use of base additives in this transesterification drastically reduces the reaction time without effecting the yields or enantioselectivities. Resolved 3-hydroxy-4-trityloxybutanenitrile has been utilized for the synthesis of enantiomerically pure 5-tosyloxymethyl-1,3-oxazolidine-2-one, which is an important intermediate for the preparation of beta-adrenergic blocking agents and oxazolidinone based antimicrobial agents. Enantiomerically pure (R)-3-hydroxy-4-trityloxybutanenitrile and (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one have been utilized in the enantioconvergent synthesis of (R)-GABOB. (c) 2006 Published by Elsevier Ltd.
• Synthesis and antibacterial evaluation of oxazolidin-2-ones structurally related to linezolid
  作者：Alessandra Ammazzalorso、Rosa Amoroso、Giancarlo Bettoni、Marialuigia Fantacuzzi、Barbara De Filippis、Letizia Giampietro、Cristina Maccallini、Domenico Paludi、Maria L. Tricca

  DOI：10.1016/j.farmac.2004.05.002

  日期：2004.9

  Compounds structurally related to the known antimicrobial drug linezolid were selected in order to evaluate the influence of electron-withdrawing properties and altered geometric features as a result of the N-substituent modification. After a preliminary study of molecular modeling, cinnamoyl-, pyridin- and pyrimidinoxazolidin-2-ones were synthesized. None of the new compounds showed antibacterial activity.
• XAMAGUTI, SIGEHKI;KATAYAMA, KADZUXIKO;OXASI, TAKEHXISA;VATANABEH, KIESI
  作者：XAMAGUTI, SIGEHKI、KATAYAMA, KADZUXIKO、OXASI, TAKEHXISA、VATANABEH, KIESI

  DOI：——

  日期：——