(3S,5R)-5-(phenylmethoxymethyl)-3-phenylselanyloxolan-2-one | 222419-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,5R)-5-(phenylmethoxymethyl)-3-phenylselanyloxolan-2-one
• CAS: 222419-07-0
• 化学式: C₁₈H₁₈O₃Se
• 分子量: 361.299
• InChiKey: BLBQUYDNDBTMFY-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5R)-5-(phenylmethoxymethyl)-3-phenylselanyloxolan-2-one 在 palladium dihydroxide 吡啶 、 盐酸 、 三乙基硼 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 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：

  苯基溴化硒 、 (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 在 三甲基氯硅烷 、 lithium hexamethyldisilazane 作用下， 生成 (3R,5R)-5-(phenylmethoxymethyl)-3-phenylselanyloxolan-2-one 、 (3S,5R)-5-(phenylmethoxymethyl)-3-phenylselanyloxolan-2-one
  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

文献信息

• Synthesis of imifuramine and its stereoisomers exhibiting histamine H3-agonistic activity
  作者：Shinya Harusawa、Tomonari Imazu、Seiichiroh Takashima、Lisa Araki、Hirofumi Ohishi、Takushi Kurihara、Yumiko Yamamoto、Atsushi Yamatodani

  DOI：10.1016/s0040-4039(99)00202-6

  日期：1999.3

  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.