5-azidomethyl-3-phenyl-1,3-oxazolidin-2-one | 367925-74-4

• 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-azidomethyl-3-phenyl-1,3-oxazolidin-2-one
• 英文别名: (l)-5-azidomethyl-3-phenyl-2-oxazolidinone；5-(Azidomethyl)-3-phenyl-1,3-oxazolidin-2-one
• CAS: 367925-74-4
• 化学式: C₁₀H₁₀N₄O₂
• 分子量: 218.215
• InChiKey: JTNYNJOPHPELKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-azidomethyl-3-phenyl-1,3-oxazolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 2.0h， 生成 5-acetamidomethyl-3-phenyl-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
• 作为产物：
  描述：

  5-(氯甲基)-3-苯基-1,3-恶唑烷-2-酮 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到5-azidomethyl-3-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  An Approach to Synthesis of 3-Aryl-2-Oxazolidinones and In Situ`Click` Assembly of 1,2,3-Triazole Oxazolidinones

  摘要：

  据报道，在 MgI2 乙醚酸盐存在下，异氰酸酯与环氧化物的加成反应简便高效，收率良好。通过点击反应，相应的 2-恶唑烷酮能轻松转化为 1,2,3-三唑-恶唑烷酮（收率极高）。

  DOI：

  10.2174/157017810791112414

文献信息

• Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04705799A1

  公开（公告）日：1987-11-10

  Novel aminomethyl oxooxazolidinyl benzene derivatives, including the sulfides, sulfoxides, sulfones and sulfonamides, such as (l)-N-[3-[4-(methylsulfinyl)phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide, possess useful antibacterial activity.

  新型氨甲基氧噁唑啉基苯衍生物，包括硫化物、亚硫酸盐、磺酰化物和磺酰胺，例如（l）-N-[3-[4-(甲基亚磺酰基)苯基]-2-氧噁唑啉-5-基甲基]乙酰胺，具有有用的抗菌活性。
• Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0127902A2

  公开（公告）日：1984-12-12

  Novel aminomethyl oxooxazolidinyl benzene derivatives, including the sulfides, sulfoxides, sulfones and sulfonamides, such as (I)-N-[3-[4- (methylsulfonyl) phenyl] -2- oxooxazolidin -5- ylmethyl] carbamic acid, methyl ester possess useful antibacterial activity.

  新型氨甲基恶恶唑烷基苯衍生物，包括硫化物、硫醚、砜和磺酰胺，如 (I)-N-[3-[4-（甲基磺酰基）苯基] -2- 恶恶唑烷-5-甲基]氨基甲酸甲酯，具有有用的抗菌活性。
• Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity
  作者：Jeffrey A. Demaray、Jason E. Thuener、Matthew N. Dawson、Steven J. Sucheck

  DOI：10.1016/j.bmcl.2008.07.087

  日期：2008.9

  C-5-substituted triazole-oxazolidinones were synthesized using a bromide catalyzed cycloaddition between aryl isocyanates and epibromohydrin followed by a three-component Huisgen cycloaddition. The library of compounds was screened for antibacterial activity against Mycobacterium smegmatis ATCC 14468, Bacillus subtilis ATCC 6633, and Enterococcus faecalis ATCC 29212. Notably, the 3-(4-acetyl-phenyl)5-(1H-1,2,3-triazol-1-yl) methyl)-oxazolidin-2-one (18) showed an MIC of 1 mu g/mL against M. smegmatis ATCC 14468, fourfold lower than the MIC measured for isoniazid. Published by Elsevier Ltd.
• BRITTELLI, DAVID R.
  作者：BRITTELLI, DAVID R.

  DOI：——

  日期：——
• GREGORY, WALTER A.
  作者：GREGORY, WALTER A.

  DOI：——

  日期：——