1-((4aR,6R,8aS)-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl)-4,5-diphenyl-1H-imidazole | 1590400-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-((4aR,6R,8aS)-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl)-4,5-diphenyl-1H-imidazole
• CAS: 1590400-88-6
• 化学式: C₂₉H₂₆N₂O₄
• 分子量: 466.536
• InChiKey: CZYGCAMISRUZPU-KDFQGOFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4,5-二苯基咪唑 、 [(4aR,8R,8aS)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl] pyridine-2-carboxylate 在 四(三苯基膦)钯 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以69%的产率得到1-((4aR,6R,8aS)-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl)-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Palladium-Catalyzed Glycosylation: Novel Synthetic Approach to Diverse N-Heterocyclic Glycosides

  摘要：

  An efficient and highly stereoselective method for the construction of N-heterocyclic glycosides is reported. This method is based on a palladium-catalyzed allylation which proceeded to provide N-heterocyclic glycosyl compounds in good-to-excellent yields with beta- or alpha-selectivity. Various N-nucleophiles were examined for this reaction and selected N-glycosyl isatin substrates were further elaborated to bis-indole sugars which have potential as antiproliferative drugs.

  DOI：

  10.1021/ol5037437

文献信息

• One-pot synthesis of β-N-glycosyl imidazole analogues via a palladium-catalysed decarboxylative allylation
  作者：Shaohua Xiang、Jingxi He、Jimei Ma、Xue-Wei Liu

  DOI：10.1039/c3cc48041k

  日期：——

  A concise and highly efficient strategy for the synthesis of N-glycosyl imidazole analogues is reported. This reaction is based on a palladium catalysed decarboxylative allylation and three steps, namely, carbamation, decarboxylation and allylation are involved. All the substrates can afford the desired products with excellent yields and selectivities.

  本报告介绍了一种合成 N-糖基咪唑类似物的简明高效策略。该反应以钯催化的脱羧烯丙基化为基础，涉及三个步骤，即碳化、脱羧和烯丙基化。所有底物都能以极高的产率和选择性得到所需的产物。