1-Benzyl-4-(4-fluorophenyl)piperidin-3-one | 916214-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Benzyl-4-(4-fluorophenyl)piperidin-3-one
• CAS: 916214-05-6
• 化学式: C₁₈H₁₈FNO
• 分子量: 283.345
• InChiKey: CZAPHFJODDJDIM-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 沸点：
  403.9±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Benzyl-4-(4-fluorophenyl)piperidin-3-one 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Enantioselective total and formal syntheses of paroxetine (PAXIL) via phosphine-catalyzed enone α-arylation using arylbismuth(V) reagents: a regiochemical complement to Heck arylation

  摘要：

  Exposure of dihydropyridinone 1 to the arylbismuth(V) reagent (p-F-Ph)(3)BiCl2 in the presence of substoichiometric quantities of tributylphosphine (10 mol %) results in aryl transfer to the transiently generated (beta-phosphonio)enolate to provide the alpha-arylated enone 2. This transformation, which represents a regiochemical complement to the Mizoroki-Heck arylation, is used strategically in concise formal and enantioselective total syntheses of the blockbuster antidepressant (-)-paroxetine (PAXIL). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.092
• 作为产物：
  描述：

  1-benzyl-1,2,3,6-tetrahydropyridin-4-en-3-one 在 三丁基膦 、 L-Selectride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 4.0h， 生成 1-Benzyl-4-(4-fluorophenyl)piperidin-3-one
  参考文献：
  名称：

  Enantioselective total and formal syntheses of paroxetine (PAXIL) via phosphine-catalyzed enone α-arylation using arylbismuth(V) reagents: a regiochemical complement to Heck arylation

  摘要：

  Exposure of dihydropyridinone 1 to the arylbismuth(V) reagent (p-F-Ph)(3)BiCl2 in the presence of substoichiometric quantities of tributylphosphine (10 mol %) results in aryl transfer to the transiently generated (beta-phosphonio)enolate to provide the alpha-arylated enone 2. This transformation, which represents a regiochemical complement to the Mizoroki-Heck arylation, is used strategically in concise formal and enantioselective total syntheses of the blockbuster antidepressant (-)-paroxetine (PAXIL). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.092

文献信息

• Enantioselective total and formal syntheses of paroxetine (PAXIL) via phosphine-catalyzed enone α-arylation using arylbismuth(V) reagents: a regiochemical complement to Heck arylation
  作者：Phillip K. Koech、Michael J. Krische

  DOI：10.1016/j.tet.2006.05.092

  日期：2006.11

  Exposure of dihydropyridinone 1 to the arylbismuth(V) reagent (p-F-Ph)(3)BiCl2 in the presence of substoichiometric quantities of tributylphosphine (10 mol %) results in aryl transfer to the transiently generated (beta-phosphonio)enolate to provide the alpha-arylated enone 2. This transformation, which represents a regiochemical complement to the Mizoroki-Heck arylation, is used strategically in concise formal and enantioselective total syntheses of the blockbuster antidepressant (-)-paroxetine (PAXIL). (c) 2006 Elsevier Ltd. All rights reserved.