(3aR,5R,6S,6aR)-6-(N-(2-azidobenzyl)-N-methylamino)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole | 1380778-63-1

• 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-(N-(2-azidobenzyl)-N-methylamino)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6S,6aR)-N-[(2-azidophenyl)methyl]-5-ethynyl-N,2,2-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-amine
• CAS: 1380778-63-1
• 化学式: C₁₇H₂₀N₄O₃
• 分子量: 328.371
• InChiKey: WPLNFAHPHYQURP-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-6-(N-(2-azidobenzyl)-N-methylamino)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以91%的产率得到(10aS,10bR,13aR,14aS)-10,12,12-trimethyl-9,10,10a,10b,-13a,14a-hexahydro[1,3]dioxolo[4',5':4,5]furo[2,3-c]benzo[g][1,2,3]triazolo[1,5-a][1,5]diazocine
  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：

  3-deoxy-3-(N-4-nitrobenzenesulfonyl-N-methylamino)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 sodium periodate 、 potassium carbonate 、 溶剂黄146 、 苯硫酚 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 21.75h， 生成 (3aR,5R,6S,6aR)-6-(N-(2-azidobenzyl)-N-methylamino)-5-ethynyl-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