exo-rac-(1S,3S,4S)-3-(4-fluorophenyl)-2-phenyl-2-azabicyclo[2.2.2]octan-5-one | 1427441-80-2

• 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: exo-rac-(1S,3S,4S)-3-(4-fluorophenyl)-2-phenyl-2-azabicyclo[2.2.2]octan-5-one
• 英文别名: 3-exo-(4-fluorophenyl)-2-phenyl-2-azabicyclo[2.2.2]octan-5-one；exo-3-(4-fluorophenyl)-2-phenyl-2-azabicyclo[2.2.2]octan-5-one
• CAS: 1427441-80-2
• 化学式: C₁₉H₁₈FNO
• 分子量: 295.356
• InChiKey: RHSJYTKQGRVDMU-YQVWRLOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 对氟苯甲醛 、 苯胺 在 tungstosilicilic acid 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以39%的产率得到endo-rac-(1S,3R,4S)-3-(4-fluorophenyl)-2-phenyl-2-azabicyclo[2.2.2]octan-5-one
  参考文献：
  名称：

  杂多酸催化的微波辅助三组分氮杂-Diels-Alder环化反应：阿尔茨海默氏病潜在药物候选物的非对映选择性合成

  摘要：

  氮杂双环[2.2.2] octan-5-ones的高非对映选择性微波辅助三组分合成 硅钨酸描述了催化的aza-Diels-Alder环化反应。一锅法涉及原位生成的席夫碱的形成及其与环己-2-烯酮。短的反应时间，良好的收率和出色的非对映选择性使这种环法成为合成目标化合物的实用且对环境有吸引力的方法。进行了初步测定，以确定产物的活性。疼痛 以及在淀粉样蛋白β原纤维形成中的抑制作用。

  DOI：

  10.1039/c0ob00638f

文献信息

• An efficient synthesis of 2,3-diaryl-2-azabicyclo[2.2.2]octan-5-ones and their acetylcholinesterase inhibitory activity
  作者：Li Huang、Jun-Pei Chen、Can Jin、Wei-Ke Su

  DOI：10.1016/j.cclet.2013.01.045

  日期：2013.4

  Abstract A series of substituted 2,3-diaryl-2-azabicyclo[2.2.2]octan-5-ones have been prepared by an efficient three-component aza-Diels–Alder cycloaddition reaction in water catalyzed by layered α -zirconium hydrogen phosphate ( α -ZrP) and sodium calix[4]arene sulfonates bearing pendant short aliphatic chains. The 18 synthesized compounds were assayed for acetylcholinesterase inhibition using mouse

  摘要通过α-磷酸氢锆层状催化剂在水中高效地进行三组分氮杂-狄尔斯-阿尔德环加成反应，制备了一系列取代的2,3-二芳基-2-氮杂双环[2.2.2]辛烷-5-酮（α-ZrP）和杯芳烃磺酸钠[4]亚芳基磺酸盐带有短的脂肪族侧链。使用小鼠乙酰胆碱酯酶测定了18种合成化合物对乙酰胆碱酯酶的抑制作用。
• Enzyme-Catalyzed Direct Three-Component Aza-Diels–Alder Reaction Using Hen Egg White Lysozyme
  作者：Yan-Hong He、Wen Hu、Zhi Guan

  DOI：10.1021/jo2016696

  日期：2012.1.6

  The direct three-component aza-Diels-Alder reaction of aromatic aldehyde, aromatic amine, and 2-cyclohexen-1-one was catalyzed by hen egg white lysozyme for the first time. Under the optimized conditions investigated in this paper, the enzyme-catalyzed aza-Diels-Alder reaction gave yields up to 98% and stereoselectivity of endo/exo ratios up to 90:10.
• Aza-Diels–Alder reaction catalyzed by novel chiral metalocomplex Brønsted acids
  作者：Victor I. Maleev、Tat’yana V. Skrupskaya、Lidia V. Yashkina、Anna F. Mkrtchyan、Ashot S. Saghyan、Michayl M. Il’in、Denis A. Chusov

  DOI：10.1016/j.tetasy.2013.01.011

  日期：2013.2

  A series of Co(III) anionic complexes of Schiff bases obtained from salicylaldehydes and enantiomerically pure amino acids has been synthesized. The outersphere counterion was exchanged by H+ and the novel chiral Bronsted acids were used to induce asymmetry into an aza-Diels-Alder reaction. The influence of the temperature, solvent polarity, and structural modification of the chiral anions on the enantioselectivity of the process has also been investigated. (C) 2013 Elsevier Ltd. All rights reserved.