(3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester | 188302-27-4

• 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: (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester
• 英文别名: (3S,4R)-methyl 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate；methyl (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate
• CAS: 188302-27-4
• 化学式: C₁₄H₁₄FNO₄
• 分子量: 279.268
• InChiKey: MXRJHOMXFFBLFI-JQWIXIFHSA-N

物化性质

• 沸点：
  413.6±45.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester 生成 (3R,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)-1-methylpiperidine-2,6-dione
  参考文献：
  名称：

  [EN] COMPOUNDS AND PROCESS TO PREPARE CHIRAL INTERMEDIATES FOR SYNTHESIS OF PAROXETINE
  [FR] COMPOSÉS ET PROCÉDÉ DE PRÉPARATION D'INTERMÉDIAIRES CHIRAUX POUR LA SYNTHÈSE DE LA PROXÉTINE

  摘要：

  公开号：

  WO2009005647A3
• 作为产物：
  描述：

  4-(4-氟苯基)-1-甲基哌啶-2,6-二酮 在 subtilisin Carlsberg 水 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.67h， 生成 (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  [EN] COMPOUNDS AND PROCESS TO PREPARE CHIRAL INTERMEDIATES FOR SYNTHESIS OF PAROXETINE
  [FR] COMPOSÉS ET PROCÉDÉ DE PRÉPARATION D'INTERMÉDIAIRES CHIRAUX POUR LA SYNTHÈSE DE LA PROXÉTINE

  摘要：

  公开号：

  WO2009005647A3

文献信息

• A Novel Chiral Base Mediated Glutarimide Desymmetrisation: Application to the Asymmetric Synthesis of (-)-Paroxetine
  作者：Nigel S. Simpkins、Daniel A. Greenhalgh

  DOI：10.1055/s-2002-35588

  日期：——

  The asymmetric desymmetrisation of certain 4-aryl substituted glutarimides has been accomplished with high levels of selectivity (up to 97% ee) by enolisation with a chiral bis-lithium amide base. The selectivity of the reaction is shown to be the result of asymmetric enolisation, followed by a kinetic resolution. One of the chiral imides synthesised was converted into the selective seratonin reuptake inhibitor (-)-paroxetine.

  某些4-芳基取代戊二酰亚胺的不对称去对称化反应通过与手性双锂酰胺碱的烯醇化作用，实现了高水平的对映选择性（高达97% ee）。反应的选择性被证明是由不对称烯醇化引起的，随后进行了动力学拆分。合成的一种手性亚胺被转化为选择性血清素再摄取抑制剂（-）-帕罗西汀。
• Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine
  作者：Christopher D Gill、Daniel A Greenhalgh、Nigel S Simpkins

  DOI：10.1016/j.tet.2003.08.046

  日期：2003.11

  The synthesis of the alkaloid jamtine and the antidepressant paroxetine have been addressed by a strategy involving asymmetric desymmetrisation of prochiral imides by a chiral lithium amide base. A short reaction sequence, starting with a cyclohexane fused succinimide, led to the structures originally reported for the alkaloid jamine and its derived N-oxide. The structures synthesised are shown not to correspond with those originally reported. A second sequence involves desymmetrisation of a 4-arylglutarimide, and provides a short enantioselective synthesis of the drug substance paroxetine. (C) 2003 Elsevier Ltd. All rights reserved.