4-(4-Fluoro-phenyl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester | 916214-18-1

• 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: 4-(4-Fluoro-phenyl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
• 英文别名: benzyl 4-(4-fluorophenyl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 916214-18-1
• 化学式: C₁₉H₁₈FNO₃
• 分子量: 327.355
• InChiKey: GYGXDHIOVNWPKI-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108 °C
• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-Fluoro-phenyl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 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 sodium tetrahydroborate 、 cerium(III) chloride 、 三丁基膦 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 28.08h， 生成 4-(4-Fluoro-phenyl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
  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.