((3aR,4R,6R,6aR)-2,2-dimethyl-6-(8-phenyl-3H-imidazo-[1,2-i]purin-3-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ((3aR,4R,6R,6aR)-2,2-dimethyl-6-(8-phenyl-3H-imidazo-[1,2-i]purin-3-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-methanol
• 化学式: C₂₁H₂₁N₅O₄
• 分子量: 407.429
• InChiKey: KCTVEBLBEUKJAD-WVSUBDOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.93
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 、 苯乙酮 在 indium(III) triflate 、 copper(l) iodide 、 氧气 作用下， 以 N-甲基吡咯烷酮 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以36%的产率得到((3aR,4R,6R,6aR)-2,2-dimethyl-6-(8-phenyl-3H-imidazo-[1,2-i]purin-3-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-methanol
  参考文献：
  名称：

  CuI-Catalyzed Aerobic Oxidative α-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles

  摘要：

  CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.

  DOI：

  10.1021/jo402134x