| 1005421-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1005421-44-2
• 化学式: C₁₉H₂₀N₄O₃
• 分子量: 352.393
• InChiKey: LFFIEHUNRQOXIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.57
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  苄基叠氮 、 Acryloyl-benzyl-carbamic acid methyl ester 在 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 1.92h， 以54%的产率得到
  参考文献：
  名称：

  Use of comparative triazolinium triflate fragmentation rates as a tool to assay relative competency of Brønsted bases in N→N proton transfer

  摘要：

  Bronsted acid-induced fragmentation of a triazoline is used as a tool to identify Bronsted base additives capable of playing the role of a proton shuttle. Relative to water, dimethyl formamide accelerates proton transfer substantially under these conditions. A series of alcohols and ethers were also used to demonstrate that the Bronsted basicity of additive functionality, not their Bronsted acidity, is responsible for their ability to accelerate proton transfer from triazoline N3 to N1. This knowledge was then used to develop a convenient two step protocol for the synthesis of oxazolidine diones from benzyl azide and an unsaturated imide that employs a substoichiometric additive for triazolinium fragmentation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.067

文献信息

• On the Nature of Rate Acceleration in the Synthesis and Fragmentation of Triazolines by Brønsted Acid:  Secondary Catalysis by Water (Hydronium Triflate)
  作者：Ki Bum Hong、Matthew G. Donahue、Jeffrey N. Johnston

  DOI：10.1021/ja0779452

  日期：2008.2.1

  Rate acceleration of the addition of benzyl azide to an electron deficient olefin is characterized using in situ IR spectroscopy. Under strictly anhydrous conditions and at depressed temperature (-20 degrees C), a triazoline intermediate is selectively formed. The stability of this protonated triazoline intermediate at -20 degrees C is indefinite, but warming of the reaction mixture to 0 degrees C

  使用原位红外光谱表征将苄基叠氮化物加成到缺电子烯烃的速率加速。在严格无水条件下和低温（-20 摄氏度）下，选择性地形成三唑啉中间体。这种质子化三唑啉中间体在 -20 摄氏度下的稳定性是不确定的，但将反应混合物加热到 0 摄氏度或以上会导致其转化为在我们之前报告中使用的条件下观察到的 β-氨基恶唑烷二酮。作为加热的替代方法，可以通过添加一当量的水来实现相同的转化。我们的实验共同证明了质子化三唑啉中间体的亚稳定性和水对三唑啉环断裂的二次催化。