(-)-(2R,4R,5S)-2-(Iodomethyl)-4-benzyloxy-5-methyltetrahydrofuran | 326805-90-7

• 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: (-)-(2R,4R,5S)-2-(Iodomethyl)-4-benzyloxy-5-methyltetrahydrofuran
• CAS: 326805-90-7
• 化学式: C₁₃H₁₇IO₂
• 分子量: 332.181
• InChiKey: GECGXNQZPXGDLF-CYZMBNFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-(2R,4R,5S)-2-(Iodomethyl)-4-benzyloxy-5-methyltetrahydrofuran 以 甲醇 、 乙醚 、 丙酮 为溶剂， 生成 (-)-(2R,4R,5S)-2-[(Dimethylamino)methyl]-4-benzyloxy-5-methyltetrahydrofuran methiodide
  参考文献：
  名称：

  Synthesis and pharmacological characterization of new chiral derivatives of muscarine and allo-muscarine

  摘要：

  Novel derivatives of natural muscarine and allo-muscarine, i.e. the benzyl ethers (-)-10 and (-)-12 and the benzoate (-)-13, were synthesized in very high enantiomeric excess. Target compounds were tested in vitro on guinea pig tissues, and their muscarinic potency was evaluated at M-2 (heart force and rate) and M-3 (ileum and bladder) receptor subtypes. The derivatives under study were also assayed in vive on pithed rat. In addition, muscarinic receptor heterogeneity was investigated by determining the affinity and the relative efficacy of compounds (-)-10, (-)-12 and (-)-13 at M-2 (heart force and rate) and M-3 (ileum and bladder) receptor subtypes. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00034-3
• 作为产物：
  描述：

  (+)-(2R,4R,5S)-2-(Iodomethyl)-4-benzoyloxy-5-methyltetrahydrofuran 在 三氟甲磺酸 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (-)-(2R,4R,5S)-2-(Iodomethyl)-4-benzyloxy-5-methyltetrahydrofuran
  参考文献：
  名称：

  Synthesis and pharmacological characterization of new chiral derivatives of muscarine and allo-muscarine

  摘要：

  Novel derivatives of natural muscarine and allo-muscarine, i.e. the benzyl ethers (-)-10 and (-)-12 and the benzoate (-)-13, were synthesized in very high enantiomeric excess. Target compounds were tested in vitro on guinea pig tissues, and their muscarinic potency was evaluated at M-2 (heart force and rate) and M-3 (ileum and bladder) receptor subtypes. The derivatives under study were also assayed in vive on pithed rat. In addition, muscarinic receptor heterogeneity was investigated by determining the affinity and the relative efficacy of compounds (-)-10, (-)-12 and (-)-13 at M-2 (heart force and rate) and M-3 (ileum and bladder) receptor subtypes. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00034-3