4-azido-2-(4-nitrophenyl)tetrahydro-2H-pyran

• 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: 4-azido-2-(4-nitrophenyl)tetrahydro-2H-pyran
• 英文别名: (2R,4S)-4-azido-2-(4-nitrophenyl)oxane
• 化学式: C₁₁H₁₂N₄O₃
• 分子量: 248.241
• InChiKey: KYTOSULIDTWQCB-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-丁烯-1-醇 、 对硝基苯甲醛 在 sodium azide 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以80%的产率得到4-azido-2-(4-nitrophenyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  A diastereoselective synthesis of 4-azidotetrahydropyrans via the Prins-cyclization

  摘要：

  A three component coupling of aldehydes, homoallylic alcohols and sodium azide is achieved in the presence of trifluoroacetic acid in dichloromethane to produce 4-azidotetrahydropyran derivatives in high yields with all cis-selectivity. The use of trifluoroacetic acid makes this procedure simple and cost-effective. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.195

文献信息

• Three-Component Coupling of Aldehydes, Homoallyl Alcohols, and Trimethylsilyl Azide: A Facile Synthesis of 4-Azidotetrahydropyrans via the Prins Cyclization
  作者：Jhillu Yadav、Basi Reddy、Tapas Maity、Gunda Narayana Kumar

  DOI：10.1055/s-2008-1067210

  日期：2008.9

  The coupling of aldehydes, homoallylic alcohols, and trimethylsilyl azide has been achieved in the presence of phosphomo­lybdic acid (PMA) in dichloromethane to produce 4-azido- ­tetrahydropyran derivatives in high yields with all cis selectivity. The use of a heteropoly acid makes this procedure simple, convenient, and cost effective.

  在二氯甲烷中存在磷钼酸 (PMA) 的情况下，已经实现了醛、高烯丙醇和叠氮化三甲基甲硅烷基的偶联，以高收率和所有顺式选择性生产 4-叠氮基-四氢吡喃衍生物。杂多酸的使用使该程序简单、方便且具有成本效益。
• A diastereoselective synthesis of 4-azidotetrahydropyrans via the Prins-cyclization
  作者：J.S. Yadav、B.V. Subba Reddy、Tapas Maity、G.G.K.S. Narayana Kumar

  DOI：10.1016/j.tetlet.2007.07.195

  日期：2007.10

  A three component coupling of aldehydes, homoallylic alcohols and sodium azide is achieved in the presence of trifluoroacetic acid in dichloromethane to produce 4-azidotetrahydropyran derivatives in high yields with all cis-selectivity. The use of trifluoroacetic acid makes this procedure simple and cost-effective. (c) 2007 Elsevier Ltd. All rights reserved.