(3R,4R)-3-acetoxy-4-(acetoxymethyl)-[1,5:1,2]-[1,2,3-triazolo]-3,4,6-trihydrobenzo[c][1,5]oxazocine | 1394834-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (3R,4R)-3-acetoxy-4-(acetoxymethyl)-[1,5:1,2]-[1,2,3-triazolo]-3,4,6-trihydrobenzo[c][1,5]oxazocine
• 英文别名: [(7R,8R)-7-acetyloxy-9-oxa-2,3,4-triazatricyclo[9.4.0.02,6]pentadeca-1(15),3,5,11,13-pentaen-8-yl]methyl acetate
• CAS: 1394834-90-2
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 331.328
• InChiKey: NVHLJZRYWIKDGK-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3aR,5S,6S,6aR)-6-((2-azidobenzyl)oxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.0h， 生成 (3R,4R)-3-acetoxy-4-(acetoxymethyl)-[1,5:1,2]-[1,2,3-triazolo]-3,4,6-trihydrobenzo[c][1,5]oxazocine
  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