ethyl 4-[(2R,5R)-5-[(1,3-dioxoisoindol-2-yl)methyl]oxolan-2-yl]imidazole-1-carboxylate | 222419-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 4-[(2R,5R)-5-[(1,3-dioxoisoindol-2-yl)methyl]oxolan-2-yl]imidazole-1-carboxylate
• CAS: 222419-27-4
• 化学式: C₁₉H₁₉N₃O₅
• 分子量: 369.377
• InChiKey: PMBKSOSAQCQVBX-MLGOLLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  90.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-[(2R,5R)-5-[(1,3-dioxoisoindol-2-yl)methyl]oxolan-2-yl]imidazole-1-carboxylate 在 一水合肼 作用下， 以82%的产率得到(+)-4(5)-[(2R,5R)-(5-aminomethyl)tetrahydrofuran-2-yl]imidazole
  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：

  ethyl 4-[(2S,3R,5R)-5-(phenylmethoxymethyl)-3-phenylselanyloxolan-2-yl]imidazole-1-carboxylate 在 palladium dihydroxide 三乙基硼 、 偶氮二甲酸二异丙酯 、 三正丁基氢锡 、 4-(二甲氨基)三苯基膦 作用下， 以 环己烯 为溶剂， 反应 6.0h， 生成 ethyl 4-[(2R,5R)-5-[(1,3-dioxoisoindol-2-yl)methyl]oxolan-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