(10aR,10bR,13aR,14aR)-12,12-dimethyl-10a,10b,13a,14a-tetrahydro-9H-[1,3]dioxolo[4',5':4,5]furo[3,2-b]benzo[f][1,2,3]triazolo[5,1-d][1,5]oxazocine | 1380778-39-1

• 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: (10aR,10bR,13aR,14aR)-12,12-dimethyl-10a,10b,13a,14a-tetrahydro-9H-[1,3]dioxolo[4',5':4,5]furo[3,2-b]benzo[f][1,2,3]triazolo[5,1-d][1,5]oxazocine
• 英文别名: (1R,15R,16R,20R)-18,18-dimethyl-14,17,19,21-tetraoxa-4,5,6-triazapentacyclo[13.6.0.02,6.07,12.016,20]henicosa-2,4,7,9,11-pentaene
• CAS: 1380778-39-1
• 化学式: C₁₆H₁₇N₃O₄
• 分子量: 315.329
• InChiKey: GYACTPSGTPMIOC-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 sodium periodate 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.0h， 生成 (10aR,10bR,13aR,14aR)-12,12-dimethyl-10a,10b,13a,14a-tetrahydro-9H-[1,3]dioxolo[4',5':4,5]furo[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