trans-1-benzyl-4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylic acid methyl ester

• 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: trans-1-benzyl-4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylic acid methyl ester
• 英文别名: methyl (3R,4S)-1-benzyl-4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylate
• 化学式: C₂₀H₁₈FNO₄
• 分子量: 355.366
• InChiKey: MZZAXJZWWKCLSG-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氰基甲酸甲酯 、 1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione 在 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以25%的产率得到trans-1-benzyl-4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine

  摘要：

  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.

  DOI：

  10.1016/j.tet.2003.08.046

文献信息

• [EN] PROCESS FOR PREPARATION OF PAROXETIN INTERMEDIATE<br/>[FR] PROCEDE DE PREPARATION D'UN INTERMEDIAIRE DE PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2001014335A1

  公开（公告）日：2001-03-01

  A trans-piperidinedione of formula (1), where R is a benzyl group and R' is an optionally substituted C1-6-alkyl, aryl-C1-6-alkyl, C1-6-allyl or aryl group, which process comprises the reaction of a cinnamate ester of formula (3), where R'' has independently the same meaning as R', with a malonamide (4) in the presence of a strong base. Compound (2) is used in the presentation of paroxetine. The preparation of paroxetine by the route from compounds (3 and 4) avoids the formation of difficult to remove impurities found in other routes.
• 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.