3-azidomethyl-2-oxazolidinone | 317366-85-1

• 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: 3-azidomethyl-2-oxazolidinone
• 英文别名: 3-azidomethyl-2-oxazolidone；3-(Azidomethyl)-2-oxazolidinone；3-(azidomethyl)-1,3-oxazolidin-2-one
• CAS: 317366-85-1
• 化学式: C₄H₆N₄O₂
• 分子量: 142.117
• InChiKey: DVSMAFFYUWLENL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  苯甲醛 、 3-azidomethyl-2-oxazolidinone 在 triphenylphosphine-bound polystyrene 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到3-[(benzylidene-amino)-methyl]-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of a Triphenylphosphine Reagent on Non-Cross-Linked Polystyrene Support:  Application to the Staudinger/Aza-Wittig Reaction

  摘要：

  [GRAPHICS]A new triphenylphosphine reagent linked to a linear polystyrene was synthesized. The reactivity of this phosphine-bound polymer is superior to that of the phosphine bound to cross-linked polystyrene. The polymer reacted very rapidly with azides to generate iminophosphoranes which could then react with aldehydes to generate imines in good yields and high purities.

  DOI：

  10.1021/ol006432w
• 作为产物：
  描述：

  2-唑烷酮 、 聚合甲醛 在 对甲苯磺酸 三(2-氯乙基)胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以89%的产率得到3-azidomethyl-2-oxazolidinone
  参考文献：
  名称：

  Synthesis of a Triphenylphosphine Reagent on Non-Cross-Linked Polystyrene Support:  Application to the Staudinger/Aza-Wittig Reaction

  摘要：

  [GRAPHICS]A new triphenylphosphine reagent linked to a linear polystyrene was synthesized. The reactivity of this phosphine-bound polymer is superior to that of the phosphine bound to cross-linked polystyrene. The polymer reacted very rapidly with azides to generate iminophosphoranes which could then react with aldehydes to generate imines in good yields and high purities.

  DOI：

  10.1021/ol006432w

文献信息

• Staudinger/aza-Wittig reactions utilizing a novel linear polymer-supported triphenylphosphine as a modified liquid-phase reagent
  作者：Hossein Mahdavi、Javad Amani

  DOI：10.1016/j.tetlet.2009.08.041

  日期：2009.10

  A new triphenylphosphine reagent linked to a linear maleimide-styrene copolymer is synthesized and is found to be effective for the formation of a variety of imines via the Staudinger/aza-Wittig reaction. This linear polymer-supported triphenylphosphine has a unique solubility behavior and provides for a simple means of purifying the desired imine from the phosphine oxide by-product. The reactivity of this polymeric reagent is Superior to that of the cross-linked polymer-supported phosphine reagent. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of a Triphenylphosphine Reagent on Non-Cross-Linked Polystyrene Support:  Application to the Staudinger/Aza-Wittig Reaction
  作者：André B. Charette、Alessandro A. Boezio、Marc K. Janes

  DOI：10.1021/ol006432w

  日期：2000.11.1

  [GRAPHICS]A new triphenylphosphine reagent linked to a linear polystyrene was synthesized. The reactivity of this phosphine-bound polymer is superior to that of the phosphine bound to cross-linked polystyrene. The polymer reacted very rapidly with azides to generate iminophosphoranes which could then react with aldehydes to generate imines in good yields and high purities.