(4RS,5SR)-1-benzyl-4-(4-fluorophenyl)-5-(methoxycarbonyl)piperidin-2-one | 612095-72-4

• 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: (4RS,5SR)-1-benzyl-4-(4-fluorophenyl)-5-(methoxycarbonyl)piperidin-2-one
• 英文别名: methyl (3R,4S)-1-benzyl-4-(4-fluorophenyl)-6-oxopiperidine-3-carboxylate
• CAS: 612095-72-4
• 化学式: C₂₀H₂₀FNO₃
• 分子量: 341.382
• InChiKey: HQCMRPPNDBQTRB-MSOLQXFVSA-N

物化性质

• 溶解度：
  溶于丙酮、二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4RS,5SR)-1-benzyl-4-(4-fluorophenyl)-5-(methoxycarbonyl)piperidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(3RS,4SR)-1-benzyl-4-(4-fluorophenyl)3-(hydroxymethyl)piperidine
  参考文献：
  名称：

  A direct entry to substituted piperidinones from α,β-unsaturated amides by means of aza double Michael reaction

  摘要：

  An intermolecular aza-double Michael reaction has been developed leading to functionalized piperidin-2-ones from simple starting materials. The method allows to utilize alpha,beta-unsaturated amides as a synthon of piperidine nucleus. The short synthesis of anti-depressant paroxetine was demonstrated by using the new methodology. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.025
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 (2E)-N-苄基-3-(4-氟苯基)丙烯酰胺 在 叔丁基二甲硅基三氟甲磺酸酯 、 三乙胺 、 叔丁醇 、 sodium methylate 作用下， 以 1,2-二氯乙烷 、 甲醇 、 甲苯 为溶剂， 反应 24.0h， 以58%的产率得到(4RS,5SR)-1-benzyl-4-(4-fluorophenyl)-5-(methoxycarbonyl)piperidin-2-one
  参考文献：
  名称：

  A direct entry to substituted piperidinones from α,β-unsaturated amides by means of aza double Michael reaction

  摘要：

  An intermolecular aza-double Michael reaction has been developed leading to functionalized piperidin-2-ones from simple starting materials. The method allows to utilize alpha,beta-unsaturated amides as a synthon of piperidine nucleus. The short synthesis of anti-depressant paroxetine was demonstrated by using the new methodology. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.025

文献信息

• Convenient Synthesis of Substituted Piperidinones from α,β-Unsaturated Amides:  Formal Synthesis of Deplancheine, Tacamonine, and Paroxetine
  作者：Kiyosei Takasu、Naoko Nishida、Akiko Tomimura、Masataka Ihara

  DOI：10.1021/jo050261x

  日期：2005.5.1

  An intermolecular aza-double Michael reaction leading to functionalized piperidin-2-ones from simple starting materials has been developed. The method allows alpha,beta-unsaturated amides to be used as a synthon of the piperidine nucleus. In addition, the utility of this methodology is demonstrated by its application to a formal synthesis of the indolo[2,3-a]quinolizidine alkaloids, (+/-)-deplancheine, (+/-)-tacamonine, and the antidepressant paroxetine.
• A direct entry to substituted piperidinones from α,β-unsaturated amides by means of aza double Michael reaction
  作者：Kiyosei Takasu、Naoko Nishida、Masataka Ihara

  DOI：10.1016/j.tetlet.2003.08.025

  日期：2003.9

  An intermolecular aza-double Michael reaction has been developed leading to functionalized piperidin-2-ones from simple starting materials. The method allows to utilize alpha,beta-unsaturated amides as a synthon of piperidine nucleus. The short synthesis of anti-depressant paroxetine was demonstrated by using the new methodology. (C) 2003 Elsevier Ltd. All rights reserved.