α-azidobenzyl ethyl ether | 336616-13-8

• 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: α-azidobenzyl ethyl ether
• 英文别名: (azido(ethoxy)methyl)benzene；[Azido(ethoxy)methyl]benzene；[azido(ethoxy)methyl]benzene
• CAS: 336616-13-8
• 化学式: C₉H₁₁N₃O
• 分子量: 177.206
• InChiKey: WFAMOBRYWIDQRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-azidobenzyl ethyl ether 在 ([2,5-Me2-3,4-Ph2(η5-C4CNHPh)]Ru(CO)(μ-CO))2 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 苯甲亚胺酸乙酯
  参考文献：
  名称：

  C–H Activation Guided by Aromatic N–H Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes

  摘要：

  Aromatic N-H ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic NH ketimines, our protocol works under mild and neutral conditions, which enabled the synthesis of isoquinolines having various functionalities such as carbonyl, ester, alkenyl, and ether groups. In addition, the imidates generated from alpha-azido ethers were successfully used for the synthesis of 1-alkoxyisoquinolines.

  DOI：

  10.1021/jo501465q
• 作为产物：
  描述：

  苄基乙基醚 在 碘叠氮化物 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以75%的产率得到α-azidobenzyl ethyl ether
  参考文献：
  名称：

  Radical Azidonation of Benzylic Positions with Iodonium Azide

  摘要：

  Introduction of an azido substituent at the α position of benzyl ethers can be achieved by treating them with IN3 in refluxing acetonitrile. Some of the products obtained after 20 min-5 h are given.

  DOI：

  10.1002/1521-3773(20010202)40:3<623::aid-anie623>3.0.co;2-g

文献信息

• Substitution of α-azido ethers with Grignard reagents and its use in combinatorial chemistry
  作者：Mukulesh Baruah、Mikael Bols

  DOI：10.1039/b110428b

  日期：2002.2.6

  α-Azidobenzyl ethers were reacted with alkyl or arylGrignard reagents in toluene to produce α-alkylbenzyl or diarylmethyl ethers in 82–94% yield. α-Azidobenzyl ethers were also reacted with multicomponent Grignard reagents to produce libraries of α-alkylbenzyl ethers.

  在甲苯中，α-叠氮苄基醚与烷基或芳基格氏试剂反应，以82-94%的产率生成α-烷基苄基醚或二芳基甲基醚。α-叠氮苄基醚还可以与多组分格氏试剂反应，生成α-烷基苄基醚的库。