(3bR,5S,5aS,8aS,8bS)-5-methoxy-7,7-dimethyl-3b,5,5a,8a,8b,10-hexahydro[1,3]dioxolo[4',5':4,5]pyrano[3,2-b]benzo[f][1,2,3]triazolo[5,1-d][1,5]oxazocine | 1380778-52-8

• 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: (3bR,5S,5aS,8aS,8bS)-5-methoxy-7,7-dimethyl-3b,5,5a,8a,8b,10-hexahydro[1,3]dioxolo[4',5':4,5]pyrano[3,2-b]benzo[f][1,2,3]triazolo[5,1-d][1,5]oxazocine
• 英文别名: (1R,15R,16S,20S,21S)-21-methoxy-18,18-dimethyl-14,17,19,22-tetraoxa-4,5,6-triazapentacyclo[13.7.0.02,6.07,12.016,20]docosa-2,4,7,9,11-pentaene
• CAS: 1380778-52-8
• 化学式: C₁₈H₂₁N₃O₅
• 分子量: 359.382
• InChiKey: OWCZNKIGLIKUQR-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 4-O-(2-azidobenzyl)-5-ethynyl-2,3-O-isopropylidene-α-D-mannopyranoside 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到(3bR,5S,5aS,8aS,8bS)-5-methoxy-7,7-dimethyl-3b,5,5a,8a,8b,10-hexahydro[1,3]dioxolo[4',5':4,5]pyrano[3,2-b]benzo[f][1,2,3]triazolo[5,1-d][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