(3aR,5R,6S,6aR)-5-ethynyl-6-methylamino-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole | 1380778-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,6aR)-5-ethynyl-6-methylamino-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6S,6aR)-5-ethynyl-N,2,2-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-amine
• CAS: 1380778-62-0
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: PNNXCJZKFWENJG-BZNPZCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-5-ethynyl-6-methylamino-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 、 1-叠氮基-2-(溴甲基)苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以82%的产率得到(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
• 作为产物：
  描述：

  3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 sodium periodate 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 苯硫酚 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 24.0h， 生成 (3aR,5R,6S,6aR)-5-ethynyl-6-methylamino-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