(3aR,5R,6S,6aR)-6-(2-azidobenzyloxy)-5-(2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole | 1380778-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aR,5R,6S,6aR)-6-(2-azidobenzyloxy)-5-(2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6S,6aR)-6-[(2-azidophenyl)methoxy]-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 1380778-27-7
• 化学式: C₁₉H₂₅N₃O₆
• 分子量: 391.424
• InChiKey: GKTHYIOWTIQJFV-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-6-(2-azidobenzyloxy)-5-(2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 在 溶剂黄146 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Design and Synthesis of 1,2,3-Triazole-Fused Chiral Medium-Ring Benzo-Heterocycles, Scaffolds Mimicking Benzolactams

  摘要：

  Based on "amide-triazole bioequivalence" principle, 1,2,3-triazole-fused chiral medium ring benzo-heterocycles capable of mimicking benzolactams were designed. Their syntheses were accomplished by cycloaddition of different sugar-derived azidoalkynes. While triazole-fused eight-membered benzo-heterocycles were formed by exclusive intramolecuclar [3 + 2] cycloaddition, attempted preparation of seven-membered analogues led to some intermolecular cycloaddition resulting in a dimeric macrocyclic product, in addition to intramolecular cycloaddition furnishing the expected heterocycle.

  DOI：

  10.1021/jo3004327
• 作为产物：
  描述：

  1-叠氮基-2-(溴甲基)苯 、 双丙酮葡萄糖 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.25h， 以85%的产率得到(3aR,5R,6S,6aR)-6-(2-azidobenzyloxy)-5-(2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Design and Synthesis of 1,2,3-Triazole-Fused Chiral Medium-Ring Benzo-Heterocycles, Scaffolds Mimicking Benzolactams

  摘要：

  Based on "amide-triazole bioequivalence" principle, 1,2,3-triazole-fused chiral medium ring benzo-heterocycles capable of mimicking benzolactams were designed. Their syntheses were accomplished by cycloaddition of different sugar-derived azidoalkynes. While triazole-fused eight-membered benzo-heterocycles were formed by exclusive intramolecuclar [3 + 2] cycloaddition, attempted preparation of seven-membered analogues led to some intermolecular cycloaddition resulting in a dimeric macrocyclic product, in addition to intramolecular cycloaddition furnishing the expected heterocycle.

  DOI：

  10.1021/jo3004327