5-ethyl-3-tosyl-1,3-oxazolidin-2-one | 129200-02-8

• 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-ethyl-3-tosyl-1,3-oxazolidin-2-one
• 英文别名: 3-(p-tolylsulfonyl)-5-ethyl-1,3-oxazolidin-2-one；5-Ethyl-3-(4-methylphenyl)sulfonyl-1,3-oxazolidin-2-one
• CAS: 129200-02-8
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: CCGMIOXCOPBDKY-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±35.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲基苯磺酰异氰酸酯 、 1,2-丁二醇 在 polymer-bound sulfonyl chloride 、 三乙胺 、 敌草腈 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以40%的产率得到5-ethyl-3-tosyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of Oxazolidinones by a Solid-Phase/Activation Cycloelimination (SP/ACE) Methodology

  摘要：

  A versatile method for the solid-phase synthesis of oxazolidinones is described, An appropriate 1,2-diol is attached to immobilized sulfonyl chloride, resulting in the selective activation of one of the alcohol functions, The subsequent reaction of the other alcohol group with an isocyanate, followed by a base-promoted cycloelimination gives an oxazolidinone, By proper choice of isocyanates, functionalities can be introduced which are essential for antibiotic activity.

  DOI：

  10.1002/1099-0690(200108)2001:15<2965::aid-ejoc2965>3.0.co;2-z

文献信息

• Mechanistic Studies of Tetraphenylstibonium Iodide-Catalyzed Cycloaddition of Oxiranes with Heterocumulenes
  作者：Masahiro Fujiwara、Akio Baba、Haruo Matsuda

  DOI：10.1246/bcsj.63.1069

  日期：1990.4

  In the selective α-cleavage cycloaddition of oxiranes with heterocumulenes catalyzed by tetraphenylstibonium iodide, the direction of oxirane fission at first stage is not significant, while the difference of reaction behaviors of two antimony alkoxide intermediates (Ph4SbOCH2CH(R1)I and Ph4SbOCH(R1)CH2I), insertion of heterocumulenes and cyclization to original oxiranes, is responsible for the unusual

  在四苯基碘化锑催化的环氧乙烷与杂枯草烯的选择性α-裂解环加成反应中，第一阶段环氧乙烷裂变的方向不显着，而两种烷氧基锑中间体（Ph4SbOCH2CH(R1)I和Ph4SbOCH(R) CH2I)，插入杂草烯并环化成原始环氧乙烷，是导致异常选择性的原因。
• Solid-phase synthesis of 3,5-disubstituted 1,3-oxazolidin-2-ones by an activation/cyclo-elimination process
  作者：Peter ten Holte、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1016/s0040-4039(98)01608-6

  日期：1998.10

  Polymer-supported sulfonyl chloride is used in the solid-phase synthesis of disubstituted 1,3-oxazolidin-2-ones. The target compounds were prepared by attaching 1,2-diols to the solid support, followed by reaction with p-toluenesulfonyl isocyanate and subsequent cycle-elimination with concurrent detachment from the resin. Oxazolidinones of high enantiopurity can be prepared with this method by employing enantiopure 1,2-diols. (C) 1998 Elsevier Science Ltd. All rights reserved.