2-[tert-butyl(dimethyl)silyl]-5-[(1S,2S,4R)-1,4-dihydroxy-5-phenylmethoxy-2-phenylselanylpentyl]-N,N-dimethylimidazole-1-sulfonamide | 222419-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[tert-butyl(dimethyl)silyl]-5-[(1S,2S,4R)-1,4-dihydroxy-5-phenylmethoxy-2-phenylselanylpentyl]-N,N-dimethylimidazole-1-sulfonamide
• CAS: 222419-29-6
• 化学式: C₂₉H₄₃N₃O₅SSeSi
• 分子量: 652.789
• InChiKey: FBVLZIRYJGFZFW-NPAAKHOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[tert-butyl(dimethyl)silyl]-5-[(1S,2S,4R)-1,4-dihydroxy-5-phenylmethoxy-2-phenylselanylpentyl]-N,N-dimethylimidazole-1-sulfonamide 在 palladium dihydroxide 吡啶 、 盐酸 、 三乙基硼 、 三正丁基氢锡 作用下， 以 环己烯 为溶剂， 反应 2.0h， 生成 (-)-ethyl 4-[(2S,5R)-(5-hydroxymethyl)tetrahydrofuran-2-yl]imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis of imifuramine and its stereoisomers exhibiting histamine H3-agonistic activity

  摘要：

  The four possible stereoisomers of a novel imidazole C-nucleoside derivative were synthesized by the efficient use of a PhSe group. Among them, (+)-4(5)-[(2R,5R)-5-(aminomethyl)tetrahydrofuran-2-yl]imidazole (imifuramine) was indicated as a novel type of histamine H-3-agonist by a brain microdialysis method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00202-6
• 作为产物：
  描述：

  (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 在 三甲基氯硅烷 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 2-[tert-butyl(dimethyl)silyl]-5-[(1S,2S,4R)-1,4-dihydroxy-5-phenylmethoxy-2-phenylselanylpentyl]-N,N-dimethylimidazole-1-sulfonamide
  参考文献：
  名称：

  Synthesis of imifuramine and its stereoisomers exhibiting histamine H3-agonistic activity

  摘要：

  The four possible stereoisomers of a novel imidazole C-nucleoside derivative were synthesized by the efficient use of a PhSe group. Among them, (+)-4(5)-[(2R,5R)-5-(aminomethyl)tetrahydrofuran-2-yl]imidazole (imifuramine) was indicated as a novel type of histamine H-3-agonist by a brain microdialysis method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00202-6