(3S,4R)-3-{[4-(苄氧基)-3-甲氧基苯氧基]甲基}-4-(4-氟苯基)哌啶 | 600135-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (3S,4R)-3-{[4-(苄氧基)-3-甲氧基苯氧基]甲基}-4-(4-氟苯基)哌啶
• 英文名称: (3S,4R)-4-(4-fluorophenyl)-3-(3-methoxy-4-benzyloxyphenoxymethyl)piperidine
• 英文别名: (3S,4R)-4-(4-Fluorophenyl)-3-[[3-methoxy-4-(benzyloxy)phenoxy]methyl]piperidine；(3S,4R)-4-(4-fluorophenyl)-3-[(3-methoxy-4-phenylmethoxyphenoxy)methyl]piperidine
• CAS: 600135-89-5
• 化学式: C₂₆H₂₈FNO₃
• 分子量: 421.512
• InChiKey: JJJAIRUIVLJSHY-URXFXBBRSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  556.4±50.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-{[4-(苄氧基)-3-甲氧基苯氧基]甲基}-4-(4-氟苯基)哌啶 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、300.0 kPa 条件下， 反应 4.0h， 以89%的产率得到4-(4-氟苯基)-3-(4-羟基-3-甲氧基苯氧基甲基)哌啶
  参考文献：
  名称：

  Synthesis of the major metabolites of Paroxetine

  摘要：

  Paroxetine is a well-known antidepressant, used worldwide in therapeutics. In comparison with other selective serotonin reuptake inhibitors, it exhibits the highest activity in serotonin reuptake inhibition. Paroxetine metabolism initially involves its demethylenation to the catechol intermediate, which is then O-methylated at positions C3 or C4. Herein, the chemistry resulting in the syntheses of these metabolites (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine and (3S,4R)-4-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl) piperidine is described starting from the common intermediate (3S,4R)-4-(4-fluorophenyl)-3hydroxymethyl-1-methylpiperidine. Additionally, the common intermediate was used to synthesize paroxetine, which had the same structure and stereochemistry as commercial paroxetine, thereby confirming our synthetic route. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00040-3
• 作为产物：
  描述：

  反式-4-(4-氟苯基)-3-羟甲基-1-甲基哌啶 在 盐酸 、 三甲胺盐酸盐 、 sodium hydride 、 potassium carbonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 (3S,4R)-3-{[4-(苄氧基)-3-甲氧基苯氧基]甲基}-4-(4-氟苯基)哌啶
  参考文献：
  名称：

  Synthesis of the major metabolites of Paroxetine

  摘要：

  Paroxetine is a well-known antidepressant, used worldwide in therapeutics. In comparison with other selective serotonin reuptake inhibitors, it exhibits the highest activity in serotonin reuptake inhibition. Paroxetine metabolism initially involves its demethylenation to the catechol intermediate, which is then O-methylated at positions C3 or C4. Herein, the chemistry resulting in the syntheses of these metabolites (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine and (3S,4R)-4-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl) piperidine is described starting from the common intermediate (3S,4R)-4-(4-fluorophenyl)-3hydroxymethyl-1-methylpiperidine. Additionally, the common intermediate was used to synthesize paroxetine, which had the same structure and stereochemistry as commercial paroxetine, thereby confirming our synthetic route. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00040-3

文献信息

• Synthesis of the major metabolites of Paroxetine
  作者：Mireia Segura、Lidia Roura、Rafael de la Torre、Jesús Joglar

  DOI：10.1016/s0045-2068(03)00040-3

  日期：2003.6

  Paroxetine is a well-known antidepressant, used worldwide in therapeutics. In comparison with other selective serotonin reuptake inhibitors, it exhibits the highest activity in serotonin reuptake inhibition. Paroxetine metabolism initially involves its demethylenation to the catechol intermediate, which is then O-methylated at positions C3 or C4. Herein, the chemistry resulting in the syntheses of these metabolites (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine and (3S,4R)-4-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl) piperidine is described starting from the common intermediate (3S,4R)-4-(4-fluorophenyl)-3hydroxymethyl-1-methylpiperidine. Additionally, the common intermediate was used to synthesize paroxetine, which had the same structure and stereochemistry as commercial paroxetine, thereby confirming our synthetic route. (C) 2003 Elsevier Science (USA). All rights reserved.