3-endo-phenyl-2-(4-bromophenyl)-2-azabicyclo[2.2.2]octan-5-one

• 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: 3-endo-phenyl-2-(4-bromophenyl)-2-azabicyclo[2.2.2]octan-5-one
• 英文别名: (1R,3S,4R)-2-(4-bromophenyl)-3-phenyl-2-azabicyclo[2.2.2]octan-5-one
• 化学式: C₁₉H₁₈BrNO
• 分子量: 356.262
• InChiKey: HPBCGLYOYMCBEQ-ZIFCJYIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 4-bromo-N-[(E)-phenylmethylidene]aniline 在 三苯基膦高氯酸盐 作用下， 以 乙腈 为溶剂， 以43%的产率得到3-endo-phenyl-2-(4-bromophenyl)-2-azabicyclo[2.2.2]octan-5-one
  参考文献：
  名称：

  Triphenyl Phosphonium Perchlorate–Catalyzed Imino Diels–Alder Synthesis of Azabicyclo[2.2.2]octan‐5‐ones

  摘要：

  A facile synthesis of azabicyclo [2.2.2]octan-5-ones by triphenyl phosphonium perchlorate-catalyzed imino Diels-Alder reaction of Schiff bases with cyclohex-2-enone.

  DOI：

  10.1081/scc-200057249

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。
• <i>N</i>-Fluorobenzenesulfonimide as Catalyst for the Three-Component Synthesis of Isoquinuclidines
  作者：D. Wu、Y-H. He、X. Deng、Z. Guan

  DOI：10.1002/jhet.1544

  日期：2013.3

  N‐Fluorobenzenesulfonimide was used for the first time as a catalyst to carry out the three‐component synthesis of isoquinuclidines with the use of various cyclohexenone (1), benzaldehydes (2), and anilines (3). The yields up to 80% and the endo/exo stereoselectivity ratios up to 19:81 were achieved.

  N-氟苯磺酰亚胺首次用作催化剂，使用各种环己烯酮（1），苯甲醛（2）和苯胺（3）进行异喹核苷的三组分合成。收率高达80％，内/外立体选择性高达19:81。
• Design of primary amine-functionalized polymer containing chiral isosorbide in the main chain for the asymmetric synthesis of isoquinuclidine derivatives
  作者：K. Hiba、K. Sreekumar

  DOI：10.1039/d1nj05868a

  日期：——

  The present article is concerned with the synthesis, characterization, and application of a novel amine-functionalized optically active polymer consisting of isosorbide units attached in the main chain. This polymer could be used as a chiral homogeneous organocatalyst for the one-pot three component asymmetric synthesis of isoquinuclidine derivatives via aza-Diels–Alder reaction. Recyclability, the

  本文关注一种新型胺官能化光学活性聚合物的合成、表征和应用，该聚合物由连接在主链上的异山梨醇单元组成。该聚合物可用作手性均相有机催化剂，用于通过aza-Diels-Alder 反应一锅三组分不对称合成异奎宁环衍生物。可回收性、催化剂用量少、后处理简单、非对映选择性优异、对映选择性适中、产品收率高，使含伯胺官能化手性聚合物（Chiral-ISO-PECH-Amine）的异山梨醇成为一种潜在的催化剂用于合成异奎宁环衍生物。
• Enantioselective oxidative-coupling of polycyclic phenols
  作者：Shinobu Takizawa、Junpei Kodera、Yasushi Yoshida、Makoto Sako、Stefanie Breukers、Dieter Enders、Hiroaki Sasai

  DOI：10.1016/j.tet.2014.01.017

  日期：2014.3

  Enantioselective oxidative-coupling of polycyclic phenols, such as 2-anthracenol, 9- or 3-phenanthrol, and 5-chrysenol was established by using vanadium(V/IV) catalysis under air or 02 as a co-oxidant. In the vanadium catalyzed reaction, the corresponding coupling products were obtained in good to excellent yields with up to 93% enantiomeric excess. (C) 2014 Elsevier Ltd. All rights reserved.
• Triphenyl Phosphonium Perchlorate–Catalyzed Imino Diels–Alder Synthesis of Azabicyclo[2.2.2]octan‐5‐ones
  作者：Gnanamani Shanthi、Paramasivan T. Perumal

  DOI：10.1081/scc-200057249

  日期：2005.5.1

  A facile synthesis of azabicyclo [2.2.2]octan-5-ones by triphenyl phosphonium perchlorate-catalyzed imino Diels-Alder reaction of Schiff bases with cyclohex-2-enone.