1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione | 511283-91-3

• 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-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione
• 英文别名: 1-Benzyl-4-(4-fluorophenyl)piperidine-2,6-dione
• CAS: 511283-91-3
• 化学式: C₁₈H₁₆FNO₂
• 分子量: 297.329
• InChiKey: CHNWDNGSXWBSNU-UHFFFAOYSA-N

物化性质

• 沸点：
  495.3±45.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione 在 吡啶 、 lithium aluminium tetrahydride 、 1-chloroethyl formate 、 chiral bis-lithium amide base 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 6.75h， 生成 帕罗西汀
  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
• 作为产物：
  描述：

  3-(4-氟苯基)戊二酸 在 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione
  参考文献：
  名称：

  Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

  摘要：

  Enantioselective reductive desymmetrization of glutarimides,has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process, that upgraded the enantioselectivity of an intermediate,hydroxy-lactam. The reaction: was generally tolerant of a number of substituents in the 4-position giving enantiomeric excesses of greater than 82%.

  DOI：

  10.1021/acs.joc.5b02177

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。
• Chemoselective Hydrogenation of Imides Catalyzed by Cp*Ru(PN) Complexes and Its Application to the Asymmetric Synthesis of Paroxetine
  作者：Masato Ito、Ayaka Sakaguchi、Chika Kobayashi、Takao Ikariya

  DOI：10.1021/ja067777y

  日期：2007.1.1

  This work represents the first catalytic hydrogenation of imides into amides and primary alcohols, in which the unique chemoselectivity is originated from the bifunctional nature of ruthenium-NH moiety in the catalyst.

  这项工作代表了第一次将酰亚胺催化氢化成酰胺和伯醇，其中独特的化学选择性源于催化剂中钌-NH 部分的双功能性质。
• 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.
• Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from <i>cis</i>-1-Amino-indan-2-ol
  作者：Ibrahim U. Kutama、Simon Jones

  DOI：10.1021/acs.joc.5b02177

  日期：2015.11.20

  Enantioselective reductive desymmetrization of glutarimides,has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process, that upgraded the enantioselectivity of an intermediate,hydroxy-lactam. The reaction: was generally tolerant of a number of substituents in the 4-position giving enantiomeric excesses of greater than 82%.